# UNITED STATES TAX COURT

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## Record

- **Collection:** Agency decision
- **Document type:** Agency decision

## Text

T.C. Memo. 1996-133

UNITED STATES TAX COURT

THEODORE A. ANDROS AND JOAN B. ANDROS, Petitioners v.
COMMISSIONER OF INTERNAL REVENUE, Respondent

Docket No. 28208-89.

Filed March 18, 1996.

Stewart Allen Smith, for petitioners.
Lawrence Davidow and Roland Barral, for respondent.

MEMORANDUM FINDINGS OF FACT AND OPINION
JACOBS,

Judge:

petitioners'

Federal

Respondent
income

taxes

determined
for

1976

deficiencies
and

1980

in

in
the

-2respective amounts of $983,966.13 and $2,338.90, and additional
interest for 1980 pursuant to section 6621(c).1
Pursuant

to

an

amended

answer,

respondent

asserts

that

petitioners are liable for additional interest for 1976 pursuant to
section 6621(c), and additions to tax for 1976 and 1980 pursuant to
section 6653(a) in the respective amounts of $49,198 and $117.
This case involves petitioner Theodore A. Andros' investment
in an options-spreads and futures-trading partnership, Tandrill
Associates (Tandrill).
litigation project.

It is part of the Arbitrage Management tax
The deficiencies result from respondent’s

disallowance of Theodore A. Andros’ allocable share of partnership
losses

from:

(1)

1979

option

spread

transactions

involving

Government securities, and (2) 1979 and 1980 futures transactions
involving commodities and Government securities.

The deficiency

for 1976 results from respondent's reduction in petitioners' net
operating loss carryback to that year from 1979.
The issues for decision are: (1) Whether respondent properly
disallowed petitioners’ allocable share of Tandrill’s losses for
1979 and 1980, pursuant to section 165(c)(2); the resolution of
this issue turns on whether the underlying partnership transactions

1

Pursuant to the Tax Reform Act of 1986, Pub. L. 99-514,
sec. 1151(c)(1), 100 Stat. 2744, former sec. 6621(d) was
redesignated as sec. 6621(c).
Unless otherwise indicated, all section references are
to the Internal Revenue Code in effect for the years in issue.
All Rule references are to the Tax Court Rules of Practice and
Procedure.

-3were entered into primarily for profit; (2) whether petitioners are
liable for additions to tax for negligence or intentional disregard
of

rules

or

regulations

for

1976

and

1980;

and

(3)

whether

petitioners are liable for additional interest for 1976 and 1980.
We find that the underlying options-spreads and futurestrading transactions by Tandrill were not entered into primarily
for

profit,

and

we

therefore

hold

that

respondent

properly

disallowed petitioners’ allocable share of Tandrill’s losses for
1979 and 1980.

We further hold that petitioners are not liable for

additions to tax for negligence or intentional disregard of rules
or regulations for 1976 and 1980, but that they are liable for
additional interest for 1976 and 1980.
FINDINGS OF FACT
Some

of

accordingly.

the

facts

have

been

stipulated

and

are

found

The stipulations of facts and the attached exhibits

are incorporated herein by this reference.
Background
Petitioners,

husband

and

wife,

resided

Florida, at the time they filed their petition.

in

Key

Biscayne,

They filed joint

Federal income tax returns for all relevant years. In April 1980,
petitioners filed a Form 1045, Application for Tentative Refund,
claiming that they were entitled to a net operating loss carryback
of $1,766,137 from 1979 to 1976.
Joan B. Andros is involved in this case by virtue of having
filed joint Federal income tax returns with her husband, Theodore

-4A. Andros.

Unless otherwise specified, the term “petitioner”

refers to Theodore A. Andros.
Petitioner received a B.A. in economics and psychology from
the University of Nebraska in 1950. He thereafter entered the U.S.
armed services and received the equivalent of an electronics
engineering degree.
Petitioner is an experienced and sophisticated businessman. He
has a basic knowledge of tax law.

Petitioner understands the

beneficial treatment accorded to capital gains and knows that
excess losses in 1 year can be carried back to the 3 prior years.
Hy-Gain Electronics Corp.
Petitioner was one of the founders of Hy-Gain Electronics
Corp. (Hy-Gain). Hy-Gain manufactured communications equipment.
From 1972 through 1976, petitioner was the executive vice president
as well as a director and shareholder of Hy-Gain.

His brother,

Andrew Andros, was Hy-Gain’s president.
On March 19, 1976, petitioner sold his shares of Hy-Gain stock
for $3.6 million.

He realized a $3,492,989 long-term capital gain

from the sale.
Real Estate Transactions
Upon leaving Hy-Gain, petitioner became involved in real
estate transactions, including condominium conversions.
he was involved in commercial real estate consulting.
investments in other business enterprises.

By 1979,

He also had

-5Richard Illingworth
Petitioner first met Richard Illingworth at a social gathering
in Miami in late 1977 or early 1978.

Petitioner informed Mr.

Illingworth that he was looking for investment opportunities. In
that regard, Mr. Illingworth explained to petitioner how he could
benefit from trading in commodity futures as well as option spreads
involving Government securities. They discussed the possibility of
forming a partnership that would engage in the trading of option
spreads and commodity futures.
Mr. Illingworth was educated in England and in the late 1960's
entered the commodities business.

He first worked at the London

Metal Exchange for the Rudolf Wolff Co., a London metal broker and
commodity trader.

In 1971, he moved to the United States, where he

was employed by C. Tennant Sons & Co., a metals and futures trading
company. Two years later, Mr. Illingworth moved to ICC Metals (a
division of International Chemical Corp.) where he traded in copper
and other metals. Subsequently, he worked for Gill & Duffus under
a trader named Herbert Weiss.
In 1977, Mr. Illingworth formed Manhattan Metals (Nonferrous)
Ltd. (Manhattan Metals), a New York corporation, involved in
physical commodities and futures trading.

He was the largest

Manhattan Metals shareholder and had a controlling interest.2

2

Mr.

The remaining stock was owned by Mr. Illingworth’s
(continued...)

-6Illingworth’s goal was to build Manhattan Metals into a commission
merchant that would compete with Merrill Lynch.
Initially,

Manhattan

Metals

brokered

relatively

small

transactions in metals, including copper. Manhattan Metals then
expanded its operations to include trading in the futures markets,
primarily in copper, gold, and silver.
By 1980, Manhattan Metals had seven employees, including two
traders--Mr. Illingworth and Herbert Weiss. Mr. Weiss was the main
trader for Manhattan Metals.

He was authorized to make trades

without discussing them with Mr. Illingworth.

One of Mr. Weiss’

responsibilities was to evaluate the prices that were being paid by
Manhattan Metals for option spreads.
Mr. Illingworth held seats on the New York Mercantile Exchange
and the New York Futures Exchange. Mr. Weiss was a member of the
Commodities Exchange, Inc. (COMEX).

Manhattan Metals was not a

member of any exchange.
In addition to Manhattan Metals, Mr. Illingworth was a partner
in several partnerships that were involved in option spreads and
commodities trading activities.
Petitioner’s Investigation of Mr. Illingworth
In considering the possibility of entering into an investment
relationship with Mr. Illingworth, petitioner engaged attorneys at

2

(...continued)
then wife and a third-party investor.

-7the Miami law firm of Paul & Thomson, accountants at Peat Marwick,
and

a

private

investigator

to

investigate

Mr.

Illingworth’s

background.

The reports petitioner received confirmed what Mr.

Illingworth

had

petitioner

that

stated
Mr.

to

be

his

background

and

Illingworth

had

expertise

in

convinced

commodities

trading.
Petitioner also consulted with accountants at Peat Marwick
regarding the tax ramifications of establishing and operating a
partnership with Mr. Illingworth.
Trading Terminology
Trading in commodity futures contracts involves tremendous
leverage and thus the potential for large gains or losses.

A

“futures” contract is a forward instrument (having a long side and
a short side) with respect to an underlying commodity.

The

contract represents a commitment to deliver (sell) or receive (buy)
a specified quantity of a commodity at a specified price at a
specified date in the future.

At the expiration of the specified

time (which is referred to by the specified month), a trader
holding a short futures contract (a contract to sell the commodity)
must

deliver

the

underlying

commodity

to

the

holder

corresponding long contract at the specified price.

of

the

A trader

holding a long futures contract (a contract to buy the commodity)
can compel the holder of the corresponding short contract to
deliver the underlying commodity.

Less than 5 percent of all

-8futures contracts actually result in delivery of the underlying
commodity; most are offset.

Futures contracts involving sales and

purchases of commodities are regulated by the Commodity Futures
Trading Commission through the Commodity Exchange Act.
A securities option is the right to buy or sell an underlying
security at a specific price (the “strike price”) and a specified
time (the expiration date). There are two types of options: “Call”
options and “put” options.

In a call option, the grantor (or

seller) of the option is required, if the buyer so desires, to sell
the underlying security to the buyer at the strike price on the
expiration date.

The buyer of a call option has the right to

“call” the security from the seller.

The buyer is “bullish” on the

underlying security; he is betting that the market price of the
underlying security will rise above the strike price.

If that

happens, the

on

option

buyer

will

purchase

the

security

the

expiration date at the strike price, which will be less than the
current market price.

With a put option, the grantor (or seller)

of the option is required, if the buyer so desires, to purchase at
the expiration date the underlying security put to him by the buyer
at the strike price.

In this latter case, the buyer is “bearish”

on the underlying security.

He is betting that the market price of

the underlying security will fall below the strike price by the
expiration date.

In that case, he will “put” the security to the

option writer, who must pay the higher strike price.

-9The price of an option, or its “premium”, is composed of two
elements:

The option’s “intrinsic value” and its “time value”.

For a call option, the intrinsic value of the option is the amount,
if any, by which the price of the underlying security exceeds the
option’s strike price.
value of the option.

The balance of the premium is the time

For a put option, the intrinsic value of the

option is the amount, if any, by which the strike price exceeds the
price of the security.
Generally, an option’s price in the marketplace will be
greater than its intrinsic value. The additional amount of premium
beyond the intrinsic value reflects that traders are willing to pay
the “time value” of money or the option’s “time premium”.

Market

participants are willing to pay this additional amount because of
the protective characteristics afforded by an option over an
outright long or short position in the underlying security.
An option is “in the money” when the option’s strike price is
less than the current market price of the underlying instrument;
i.e., when it would be economically favorable for the option holder
to exercise the option. An option is “out of the money” when it
would be economically unfavorable to exercise the option. When the
option strike price equals the market price of the underlying
security, an option is “at the money”.
In the futures market, a “spread” consists of the simultaneous
establishment of two opposite positions for delivery of the same

-10commodity in different delivery months.

Such a spread consists of

two “legs”: One is the purchase of a commodity for delivery at a
specific future date, while the other is the simultaneous sale of
the same commodity for delivery at a different specified future
date.

Although there are variations in spreads, all of them have

a simultaneous purchase and sale.
In

the

options

market,

a

“spread”

(sometimes

called

a

“straddle”) is a position maintaining simultaneously both long and
short options of the same type (i.e., puts or calls) or of
different types in the same class. A “vertical spread” in the
options market consists of purchasing an option at one strike price
and simultaneously selling an option at another strike price, where
the options are identical in all other respects.3 “Vertical put
spreads” are positions in which a trader has both long (purchased)
puts

and

short

(sold)

puts

in

the

same

underlying

different strike prices for the same maturity month.

asset

at

The spread is

a “credit spread” when the price paid for the long position is less
than the price received for the short position so that the trader’s
account shows a cash credit.
“sold” the spread.

The trader is then considered to have

A trader is said to have “purchased” the spread

(a “debit spread”) when the price paid for the long position is

3

The following is a typical vertical spread:
Buy 1 June 90 call
Sell 1 June 95 call

-11less than the price received for the short position so that the
trader’s account shows a debit.
“Butterfly spreads” occur when a trader holds three positions
in

the

same

underlying

asset

in

puts

or

calls

in

the

same

expiration month at three different strike prices, with the highest
and lowest

strike

positions

one-half

the

size

of

the

middle

position.4
A General Description of Tandrill’s Trading Plan
On August 22, 1979, petitioner and Mr. Illingworth formed
Tandrill,

a

general

partnership

under

the

laws

of

Florida.

Tandrill is a combination of the names of its two partners: T.
ANDROS and R. ILLINGWORTH. Petitioner contributed the major portion
of the funding for the partnership while Mr. Illingworth agreed to
conduct Tandrill’s trading activity.

As stated in the partnership

agreement, the purpose of Tandrill was to trade in:
commodities
of
every
nature,
foreign
currencies, U.S. Treasury Bills, U.S. Treasury
Bonds,
GNMA
Certificates[5]
and
other

4

A “butterfly” spread is a balanced straddle position.
An example of a butterfly spread in gold would involve the
purchase of one contract of February gold, the short sale of two
contracts for April delivery, and the purchase of one contract of
June gold. If the price of gold goes up, the investor will profit
on his two long contracts in February and June and lose a
substantially like amount on his two short April contracts. The
“butterfly” spread gets its name because it has a heavy body in
the center (in this case the two April short contracts) and
lighter wings on the side (in this case the one long contract
each in February and June).
5

GNMA’s, sometimes referred to as “Ginnie Maes”, are
long-term coupon-bearing securities issued through the Government
(continued...)

-12government (foreign or domestic) financial
instruments and futures contracts and options
with respect to the foregoing, and in
connection
therewith
to
use
arbitrage,
spreading,
margin
and
other
leveraging
devices, and such other techniques deemed
appropriate.
Petitioner contributed $300,000 to Tandrill in exchange for a
93.75-percent partnership interest; Mr. Illingworth contributed
$20,000 in exchange for a 6.25-percent interest.
On the same date Tandrill was formed (August 22, 1979),
Tandrill entered into a Management Agreement with Manhattan Metals,
whereby it was agreed that Manhattan Metals would “manage, buy,
sell, sell short, redeem and otherwise invest, reinvest and trade
in

commodities

of

every

nature”

on

Tandrill’s

behalf.

The

Management Agreement authorized Manhattan Metals to: (1) Perform
administrative functions for Tandrill; (2) employ Wilcap Advisors
(Wilcap)6 as an adviser in its trading activities; and (3) share in
commissions or fees that Tandrill paid.
Tandrill paid Manhattan Metals a retainer and organization fee
of $10,000 upon execution of the Management Agreement. On an
ongoing basis, Tandrill was required to pay Manhattan Metals an

5

(...continued)
National Mortgage Association that represent undivided interests
in specific pools of Government-guaranteed mortgages. Such
certificates are backed by the full faith and credit of the
Federal Government.
6

Messrs. Paul Willensky and Mark Sherman were the
principals of Wilcap. Mr. Illingworth had known Messrs. Willensky
and Sherman less than a year, and had not previously dealt with
them, when he decided to use their company as an adviser to
Manhattan Metals.

-13annual

management

fee

of

three-fourths

of

1

percent

of

the

aggregate value of Tandrill’s investments with Manhattan Metals
(including the value of commodities subject to futures contracts),
the value of premiums paid for options, and cash on hand.

Such fee

was capped at a maximum of $50,000, or $12,500 per calendar
quarter, for the period ending September 30, 1980, and at a maximum
of $25,000 per year, or $6,250 per calendar quarter, thereafter.
The Management Agreement had no fixed termination date; it
could be terminated on 30 days’ notice by either party. The
agreement provided that, if petitioner terminated the agreement
before September 30, 1980, Tandrill would pay Manhattan Metals the
difference between $50,000 and the sum of the quarterly fees that
had been paid to Manhattan Metals for that period.
Manhattan

Metals

was

exclusively for Tandrill.

not

required

to

perform

services

Petitioner understood that although

Manhattan Metals would conduct Tandrill's trading activities and
that

Mr.

Illingworth

would

be

in

charge

of

deciding

the

partnership’s trading positions, Mr. Illingworth would be assisted
in doing so by others.

Petitioner had no interest in managing

Tandrill’s day-to-day trading activities; he merely wanted the
right to make suggestions and review documents.
At the time that the trades were undertaken, petitioner did
not understand the exact nature of Tandrill's trading activities,
or the mechanics and theories of commodities trading. Although Mr.
Illingworth sent petitioner periodic updates regarding Tandrill’s

-14trading activity, petitioner did not closely monitor the trades
Manhattan Metals performed for Tandrill.
Tandrill's net asset value decreased each calendar quarter
during 1980.
Tandrill's Transactions
Arbitrage

Management

Investment

Company

(Arbitrage

Management)7 and Pershing & Co. (Pershing) performed brokerage
services

for

Tandrill

with

respect

to

Treasury

bill

options

transactions; they also made the market in which such transactions
were executed.

Arbitrage Management or Pershing was on the "other

side" of each Treasury bill option transaction that Tandrill
entered.

A.C.L.I. International Commodity Services, Inc. (ACLI),

and Bache Halsey Stuart Shields, Inc. (Bache), performed brokerage
services for Tandrill with respect to its commodity futures trading
transactions.
a.

Options Transactions

The Treasury bill options transactions involved herein were
cleared through Pershing and Arbitrage Management.8 See appendices
A-D

for

a

list

of

Tandrill’s

put-option

positions.

Messrs.

Willensky and Sherman of Wilcap handled the trades on behalf of
Manhattan Metals. They made all the trading decisions with respect

7

Arbitrage Management Investment Company has been
involved in other cases in this Court. See, e.g., Fox v.
Commissioner, 82 T.C. 1001 (1984); Manko v. Commissioner, T.C.
Memo. 1995-10.
8

Pershing and Arbitrage Management "wrote" the options
comprising the spreads that Tandrill established.

-15to the Treasury bill options transactions, after discussing with
Mr. Illingworth the "general parameters" of such trading.

Wilcap

decided which brokerage house would execute a particular options
transaction.
The options transactions did not occur on a regulated exchange
but instead were conducted over the counter.9

Current trading

prices for the option spreads, or the constituent put options, were
not published daily.

There was no publicly available mechanism

through which a trader in Treasury bill options could ascertain the
current price of his positions.

No steps were taken to insure that

Tandrill paid or received fair prices for its positions in Treasury
bill options.
All of the options transactions that Tandrill entered into
possessed the following characteristics: (1) They were part of
eight "vertical put" straddles or spreads; (2) all of the spreads
were opened and closed out in 1979; (3) the underlying commodities
were Treasury bills; (4) when the spreads were opened, all of the
puts were "in the money"; (5) all of the spreads were closed out
through "offset" before the date of issuance of the underlying
Treasury bills; (6) the options spreads were purchased as a unit
rather than as separate legs; and (7) the spread between exercise
prices varied from a minimum of .06 to a maximum of .125.

None of

the trade spreads was profitable.
9

In 1979 there were three or four dealers who made a
market in over-the-counter Treasury bill options.

-16Six of the options spreads were executed through Pershing.
These spreads were all credit spreads, so-called because Tandrill
received money or a credit to its account when it established the
spreads.10

These spreads involved the sale of put options having

a higher dollar exercise price and the purchase of puts with a
lower dollar exercise price.

The other two options spreads were

executed through Arbitrage Management.

Both of these spreads were

debit spreads, so-called because Tandrill paid money or suffered a
debit of its account when it established the spreads.

These

spreads involved the sale of put options having a lower dollar
exercise price and the purchase of put options having a higher
dollar exercise price.
b.

Futures Transactions

Tandrill's futures transactions generally had the following
characteristics: (1) Most took the form of straddles or spreads;
(2) Tandrill's British pound and Swiss franc futures trading took
place on the International Monetary Market; (3) the Treasury bill
futures trading took place on the Chicago Mercantile Exchange; (4)
the Treasury bond and GNMA futures trading took place on the
Chicago Board of Trade; (5) the sugar futures trading took place on
the Coffee, Cocoa and Sugar Exchange; (6) the gold, silver, and
copper futures trading took place on the COMEX; (7) the trading in

10

Vertical spreads, like individual options, can either
be purchased or sold. These spreads were sold by Tandrill.

-17"physical" copper took place through Manhattan Metals;11 and (8) all
of the futures positions were closed out through "offset".
In 1979 and 1980, Tandrill entered into futures transactions
in gold, silver,12 copper, and Treasury bills through Bache.

With

respect to these transactions: (1) The gold and silver trading
began on November 1, 1979, and the copper trading began on November
14, 1979; (2) all the gold, silver, and copper futures transactions

11

Tandrill's trading in "physical" copper had the
following characteristics: (1) Delivery or receipt of the
commodity was never intended and never took place; (2) all gains
and losses were cleared through a "difference account"; (3)
Manhattan Metals was on the other side of each transaction that
Tandrill entered into; Manhattan Metals was the source of any
profits and losses Tandrill realized; and (4) the "physical"
copper trades did not occur on an exchange. Respondent could not
determine how the “physical copper” transactions affected
petitioners’ or Tandrill’s tax returns, and the tax consequences
of these transactions are not in dispute here.
12

The price of silver fluctuated substantially on Nov.
21, 23, and 27, 1979. The following chart (taken from the COMEX
Statistical Yearbook for 1979) indicates the price movement and
number of contracts of September 1980 silver traded each day
between Nov. 15 and 27, 1979:
Price
Contracts
Movement
Traded
Date
Nov. 15
Nov. 16
Nov. 19
Nov. 20
Nov. 21
Nov. 23
Nov. 26
Nov. 27

down 7.8
up 7
up 2
up 3
down 21
up 31.5
up 7
up 40

605
235
126
80
4,463
817
173
4,240

Of the 721 silver contracts that Tandrill closed out in
1979, 718 were closed out on either Nov. 21 or 27, 1979. On Nov.
21, 1979, Tandrill closed out 359 silver contracts by
repurchasing 119 May 1980 silver contracts and 240 December 1980
silver contracts. On Nov. 27, 1979, Tandrill closed out 359
silver contracts by repurchasing 108 March 1981 silver contracts,
75 March 1980 silver contracts, and 176 September 1980 silver
contracts.

-18involved balanced straddles; some were butterfly spreads;13 (3) in
1979, Tandrill,

in

its

account

with

Bache,

entered

into

160

contracts of copper futures straddles, 330 contracts of

gold

futures straddles, and 1,110 contracts of silver futures straddles;
(4) in 1979, Tandrill closed out by offset 100 of the copper
futures contracts, 164 of the gold futures contracts, and 697 of
the

silver

futures

contracts,

realizing

a

net

loss

of

$1,772,139.10, including commissions; (5) every futures spread
Tandrill closed out in 1979 involved the realization of a loss,
with the exception of an aggregate gain of $612 realized on 20 July
1980 copper

contracts;

and

(6)

on

a

weighted

average

basis,

Tandrill's 1979 silver, gold, and copper spreads were kept open an
average 12.10 days.14

13

For example, on Nov. 26, 1979, Tandrill purchased 20
May 1980 copper contracts, sold 40 July 1980 copper contracts,
and purchased 20 September 1980 copper contracts.
14

HOLDING PERIODS, 1979 TRADES
DATE
SOLD

DATE
BOUGHT

QUANTITY

DESCRIPTION

NUMBER
OF DAYS

DAYS X
QUANTITY

11/01/79
11/06/79
11/15/79

11/21/79
11/21/79
11/21/79

18
146
119

Apr. 81 Gold
Apr. 81 Gold
May 80 Silver

20
15
6

360
2,190
714

11/01/79
11/02/79
11/05/79

11/21/79
11/21/79
11/21/79

73
79
88

Dec. 80 Silver
Dec. 80 Silver
Dec. 80 Silver

20
19
16

1,460
1,501
1,408

11/15/79
11/21/79
11/21/79

11/27/79
11/27/79
11/27/79

108
75
132

Mar. 81 Silver
Mar. 80 Silver
Sept. 80 Silver

12
6
6

1,296
450
792

11/21/79

11/27/79

44

Sept. 80 Silver

6

264

(continued...)

-19Tandrill realized gains and losses in 1979 and 1980 from
commodity futures transactions, with respect to which Bache was the
broker, in the following amounts:
Commodity

Net Gain/Loss
1979

Net Gain/Loss
1980

Silver
Gold
T-Bill futures
Copper
Other
Total

($1,402,729.30)
( 264,033.00)
199,502.00
( 105,440.00)
--(1,572,700.30)

$738,631.30
207,874.60
(44,448.80)
(35,821.10)
(16,940.90)
849,295.10

In 1980, Tandrill entered into futures transactions in copper,
gold, sugar, Treasury bills, Treasury bonds, and GNMA's through
ACLI.

Tandrill realized $749,143.50 in net losses with respect to

the commodity futures transactions.

For example, on June 26-27,

1980, Tandrill entered into a "spread of a spread" involving GNMA
and Treasury bond contracts: (a) It purchased 30 March 1981 GNMA
contracts and sold 30 September 1981 GNMA contracts; and (b) it
purchased 30 September 1981 Treasury bond contracts and sold 30

14

(...continued)

11/27/79
11/14/79

12/26/79
11/21/79

3
10

Dec. 80 Silver
Mar. 80 Copper

29
7

87
70

11/14/79
11/21/79
11/23/79

11/23/79
12/03/79
12/03/79

10
10
10

Mar. 80 Copper
July 80 Copper
July 80 Copper

9
12
10

90
120
100

11/26/79
11/26/79
11/26/79

12/13/79
12/19/79
12/07/79

20
20
20

July 80 Copper
July 80 Copper
Sept. 80 Copper

17
23
11

340
460
220

TOTALS

985

Average days per transaction
Average days per contract (11,922/985)

11,922
13.56
12.10

-20March 1981 Treasury bond contracts.

On October 28, 1980, Tandrill

entered into another "spread of a spread" involving GNMA and
Treasury bond

contracts:

(a)

It

purchased

30

June

1981

GNMA

contracts and sold 30 March 1981 GNMA contracts; and (b) it
purchased

30

June

September

1981

1981

Treasury

Treasury

bond

bond

contracts

contracts.

The

and

sold

October

30

1980

transactions resulted in a $327,030 loss on the GNMA contracts and
a $368,280 loss on the Treasury bond contracts. This left Tandrill
with unrealized profits of $691,406.25 in its open positions.
Tandrill's open positions were liquidated in 1981.
Tandrill’s Liquidation
Tandrill ceased operations in 1981; at this time, its capital
had dwindled to approximately $10,000. Petitioner received only one
distribution

from

Tandrill,

in

the

amount

of

$9,782,

which

represented his proportionate share of Tandrill's net assets on the
1981 liquidation date.
Tandrill's Forms 1065
Peat

Marwick’s

New

York

office

prepared

Tandrill’s

partnership returns (Forms 1065) for 1979 and 1980.15
a.

1979

On its 1979 partnership return, Tandrill reported an ordinary
loss of $1,858,743 on Treasury bill options and claimed deductions

15

Petitioners introduced into the record Tandrill’s 1979
and 1980 yearend financial statements. However, they failed to
present evidence proving the reliability of such documents. We
have therefore not utilized these statements in making our
determination.

-21for a management fee and accounting fee of $22,500 and $270,
respectively.

These ordinary losses arose from purchased put

options on Treasury bills.

Each of Tandrill's purchased put

options was closed out at a loss in 1979.
Tandrill also reported short-term capital gains of $163,666 on
this

return,

computed

as

the

excess

of

short-term

gains

of

$1,736,366 over short-term losses of $1,572,700. The $1,736,366 in
short-term capital gains arose from the sale of put options on
Treasury bills. The $1,572,700 in short-term capital losses arose
from futures transactions in gold, silver, copper, and Treasury
bills.
b.

1980

On its 1980 partnership return, Tandrill reported an ordinary
loss of $19,428 on Treasury bill futures transactions, interest
income

of

$36,065,

and

deductions

for

a

management

fee

and

accounting fee of $43,750 and $9,700, respectively. Tandrill also
reported

short-term

capital

capital gains of $1,509,077.
and

long-term

capital

losses

of

$918,244

and

long-term

Both the short-term capital losses

gains

arose

from

commodity

futures

transactions.
Petitioners' 1979 and 1980 Federal Income Tax Returns
Peat Marwick’s Miami office prepared petitioners’ returns for
both years in issue. Petitioner provided Peat Marwick with his tax
information and copies of his 1979 and 1980 Schedules K-1 from
Tandrill for use in Peat Marwick’s preparation of petitioners’ 1979
and 1980 returns.

-22Petitioners reported the following amounts of income and loss
on

their

1979

and

1980

returns

with

respect

to

petitioner's

investment in Tandrill:
Year

Income
(Loss)

Short-Term
Capital Gain (Loss)

Long-Term
Capital Gain

1979

($1,758,908)

$153,437

---

1980

(34,512)

(860,854)

$1,414,760

In April 1980, petitioners filed a Form 1045, Application for
Tentative Refund, claiming entitlement to a net operating loss
carryback of $1,766,137 from 1979 to 1976.
Notice of Deficiency
In

the

notice

of

deficiency,

respondent

disallowed

petitioners’ allocable share of losses arising from Tandrill’s
transactions on the premise that no profit motive existed with
respect to the transactions.16 Respondent determined the following
corrected amounts of income and loss petitioner realized through
his investment in Tandrill:
Year

Income
(Loss)

Short-Term
Capital Gain

Long-Term
Capital Gain

1979

$5,010

---

---

1980

33,811

---

---

16

Respondent also determined that “the transactions at
issue were either shams or devoid of the substance necessary for
recognition for federal income tax purposes.” Respondent’s
amended answer reiterated this position. However, at trial,
respondent’s counsel informed the Court that the only issue for
decision in this regard is whether Tandrill entered into the
transactions at issue primarily for profit. We therefore will
assume that Tandrill’s transactions were not shams.

-23Accordingly, the adjustments respondent made in the notice of
deficiency increased (decreased) petitioners' income and loss items
as follows:
Year

Income
(Loss)

Short-Term
Capital Gain

Long-Term
Capital Gain

1979

$1,763,918

($153,437)

---

1980

68,323

860,854

($1,414,760)

The adjustment to petitioners' 1979 income results in a reduction
of

petitioners'

net

operating

loss

carryback

to

1976

from

$1,766,137 to $146,279, and an increase of $1,619,858 in taxable
income for 1976.

The disallowed deductions arose from Tandrill's

transactions involving Treasury bill option spreads and commodity
futures.17
OPINION
Issue 1.

Tandrill Losses

The first issue for decision is whether respondent properly
disallowed petitioners’ allocable share of Tandrill’s 1979 and 1980
losses pursuant to section 165(c)(2).

This issue turns on whether

the underlying partnership transactions were entered into primarily
for profit.

Petitioners have the burden of proof in this regard.

Rule 142(a).
17

We note that prior to the trial in this case, the
Internal Revenue Service (IRS) audited Mr. Illingworth’s 1978-80
tax years, disallowing loss deductions that he had claimed
relating both to Tandrill’s transactions at issue herein and to
other transactions involving other partnerships. The IRS
determined that Tandrill’s transactions had not been entered into
for profit. Mr. Illingworth ultimately accepted an IRS
settlement offer based on this determination.

-24Respondent

contends

that

the

purpose

of

the

options

transactions was to generate corresponding amounts of ordinary
losses and short-term capital gains in 1979, while the purpose of
the commodity futures transactions was to generate short-term
capital losses

in

1979

and

long-term

capital

gains

in

1980.

Respondent posits that at the time the transactions were entered
into, Tandrill’s general partners (petitioner and Mr. Illingworth)
expected to realize economic losses rather than economic profits.
According to respondent, petitioner was aware that the economic
consequences of the transactions entered into by Tandrill were de
minimis as compared to their potential tax benefits.

On the other

hand, petitioners argue that the transactions at issue were entered
into with both a profit motive and profit potential.

We agree with

respondent.
Respondent and petitioners each rely on reports and testimony
of their respective experts.

As the trier of fact, we must weigh

the

these

evidence

presented

by

experts

in

light

of

their

demonstrated qualifications as well as all other credible evidence.
Estate of Christ v. Commissioner, 480 F.2d 171, 174 (9th Cir.
1973), affg. 54 T.C. 493 (1970). We are not bound by the opinion of
any expert witness when that opinion is contrary to our own
judgment.

Chiu v. Commissioner, 84 T.C. 722, 734 (1985).

-25The Parties’ Experts
Mr. Natenberg
Respondent’s first expert witness, Sheldon Henry Natenberg,
received a B.A. in mathematics from the University of Illinois.
After working in unrelated fields for 10 years, he became an
independent option trader in 1982.

Mr. Natenberg is an options

consultant and conducts educational seminars for traders all over
the world. He has written a book, Option Volatility and Pricing
Strategies, which was published in 1988 and revised in 1994.

Mr.

Natenberg is a member of the Chicago Board of Trade.
Mr. Natenberg's report, rebuttal report, and testimony solely
addressed Tandrill's 1979 options spreads. Mr. Natenberg testified
that Tandrill’s options trades consisted of vertical put spreads,
with all the puts being in the money. Grouping the trades by
opening date and exercise price, he further testified that the
trades consisted of eight different put vertical spreads. Six
spreads were initially sold and later bought back, and two spreads
were initially purchased and later sold out.

Mr. Natenberg opined

that in every one of the six spread positions initiated with the
sale of a vertical put spread, the spread was sold at a price so
low that a profit could be considered at best highly unlikely.

He

further stated that when the spread positions were closed, they
then were bought back at a price greater than the maximum possible
spread value. Thus, according to Mr. Natenberg, profit was not the
motivation for the trades.

-26Mr.

Natenberg

testified

that

in

closing

transactions, Tandrill experienced a cash outflow.

out

the

spread

By paying more

than the theoretical maximum value to close out the spreads,
Tandrill reduced its overall profits (if any) or increased its
overall losses.

Mr. Natenberg explained that over the life of an

option, the option’s value will vary depending on current market
conditions and the likelihood of changing conditions in the future.
He referred to the Black-Scholes Model.18

The Black-Scholes Model

is a mathematical refinement of the premise that changes in value
of an underlying asset are random.

The Black-Scholes Model uses

the laws of probability to determine the price at which an option
would have to trade so that neither the buyer nor the seller of the
option would show a profit in the long run.19
Mr. Natenberg opined that at the moment of expiration, an
option can take only one of two values:

Zero if it is out of the

money, and intrinsic value if it is in the money. Thus, at
expiration of the option it is always possible to calculate the
maximum potential profit or loss resulting from any individual
option trade as well as from a trade consisting of multiple
options.

Further, the maximum value of a put option spread is the

18

The Black-Scholes Model was developed by Fisher Black
and Myron Scholes in 1973. It is a tool for analyzing an
option’s value.
19

The Black-Scholes Model requires five inputs in order
to generate a theoretical value: Exercise price, expiration date,
price of the underyling instrument, prevailing interest rate, and
volatility.

-27difference between the exercise prices of the purchased and sold
puts, and the minimum value is zero.
According to Mr. Natenberg, the amount of money or credit that
Tandrill received upon the establishment of all six of its credit
spreads was always substantially outside (less than) the range of
values indicated by the Black-Scholes Model. In addition, the
amount of money or credit that Tandrill received upon closing out
the two debit spreads through Arbitrage Management was always
substantially outside (less than) the range of values indicated by
the Black-Scholes Model.
Mr. Natenberg analyzed Tandrill’s trades based on a comparison
of the trade prices with two numbers:

The maximum possible value

of

expiration,

each

vertical

spread

if

held

to

and

a

price

evaluation of each spread using the Black-Scholes Model. See
appendix E for Mr. Natenberg’s Trade Analysis.

Mr. Natenberg

concluded that Tandrill’s options trades were done at prices that
“practically ensured that they would result in a loss.”20

20

Mr. Natenberg gave as an example Tandrill’s first
trade, on Sept. 20, 1979, where the partnership sold the
97.50/97.625 put spread 47 times. He stated that if the price of
the underlying Treasury bill were at or below 97.50 at
expiration, the spread would have a maximum value of $58,750. If
the price of the underlying Treasury bill were at or above 97.625
at expiration, the spread would be worthless. At the time the
trade was made the Treasury bill price was 97.45. Because this
price was below 97.50, there was, in Mr. Natenberg’s opinion, a
far greater chance for the spread to be worth at expiration its
maximum value of $58,750 than its minimum value of zero. Thus,
according to Mr. Natenberg, the value of the spread should be
closer to $58,750 than to zero. Mr. Natenberg confirmed this by
(continued...)

-28Mr. Maduff
Respondent’s other expert, Michael L. Maduff, received a B.A.
in economics from the University of Iowa.

Between 1965 and 1984,

he was chief executive officer of Maduff & Sons, Inc., a licensed
futures commission merchant and clearing member of the Chicago
Mercantile Exchange.

After 20 years in business, he went to law

school at Northwestern University and received a J.D. in 1988.
Since 1988 he has been a practicing attorney, as well as a
consultant and expert witness regarding the futures industry.
Mr. Maduff's report and testimony concern Tandrill's 1979-81
commodity and futures transactions.

Mr. Maduff testified that a

spread

futures

in

gold,

silver,

or

copper

is

principally

a

speculation on interest rates rather than a speculation on the
value of the metal itself.21

20

(...continued)
using the Black-Scholes Model to evaluate the spread. From this
analysis he determined that a reasonable value for this spread
would have been somewhere between $32,638 and $50,553. But
Tandrill actually sold the spread for $25,004. Even allowing for
subjective judgments among different market participants, Mr.
Natenberg opined that this was well below the price any
knowledgeable trader would have placed on the spread.
21

Mr. Maduff explained that in 1979 and 1980, precious
metals and long-term interest rates made historic highs and
experienced great volatility. While absolute prices of the
metals may be volatile, the relative price for different delivery
months of the same metal remained fairly constant, reflecting the
cost of maintaining an inventory of the metal over time, socalled carrying costs, with interest being the major component of
these carrying costs.

-29Mr. Maduff stated that the documentation petitioners provided
concerning Tandrill’s futures trading, while not complete, was
sufficient for him to conclude that Tandrill in fact made trades on
the futures exchanges and that those trades generally were “tax
straddles with no economic objective or effect other than to move
income from one year to the next with minimal market exposure and
no hope of profit.”

He testified that while the commissions Bache

and ACLI charged Tandrill do not appear on the documents provided,
he was able to extrapolate the sum of commissions and fees charged
from the information supplied, namely $52.70 per contract charged
by Bache, and $41.50 for gold and $26.50 for copper charged by
ACLI.22

22

The charges connected with the execution of Tandrill’s
futures trading took two distinct forms: Broker’s commissions
(and associated fees) and market slippage, or the bid/ask price
spread. (The bid/ask price is the difference between the prices
at which floor traders are willing to buy and prices at which
they are willing to sell.) After studying the Bache and ACLI
monthly statements, Mr. Maduff concluded that Bache and ACLI
charged commissions and associates fees on a per-contract, roundturn basis. (A per-contract basis means that the commissions and
fees are the same for each contract of a particular commodity
traded, without regard to the price. A round-turn basis means
that no commission is charged when a position is established
(whether long or short), but rather the broker waits until the
position is closed out with an offsetting sale or purchase and
then charges a single fee for the entire round-turn transaction.)
Tandrill also paid execution costs, meaning the markup the
investor pays to the floor trader every time he buys and the
markdown he suffers every time he sells. Thus, commissions are
paid only when a position is closed out while execution costs are
encountered when an investor enters his position and again when
he closes it out. The total marginal costs of a single contract
include two execution costs and one commission cost.

-30The Bache Trades
Mr. Maduff was able to draw conclusions only with respect to
Tandrill’s 1979 trading through Bache because the documents that
were presented regarding Tandrill’s 1980 trades through Bache were
incomplete.
a.

Treasury Bills

The

Treasury

bill

trading

began

continued through the end of the year.

in

September

1979

and

Mr. Maduff stated that

taken in isolation, the Treasury bill trading would appear to have
been undertaken with a profit motive.

But, he went on to say,

because Tandrill failed to provide records of other interest rate
transactions it may have engaged in during the period, it is
possible that, when viewed in conjunction with transactions in
other brokerage accounts, the Treasury bill positions through Bache
would prove to be mere hedges against these other positions and
thus not
b.

reasonably

likely

to

have

resulted

in

net

profits.

Gold, Silver, and Copper Transactions

Mr. Maduff concluded that Tandrill’s 1979 gold, silver, and
copper transactions were not motivated by the desire to achieve an
economic profit and were taken solely for tax purposes. The gold
and silver trading began on November 1, 1979, and the copper
trading began on November 14, 1979.

Every transaction was a

perfectly balanced straddle with an equal number of purchases and

-31sales on each day.

A few of these transactions were butterfly

spreads.23
At times, Tandrill established positions that appeared to be
regular, nonbutterfly spreads but which, on closer examination, had
little risk involved.

For instance, in early November 1979,

Tandrill purchased February 1981 gold contracts and sold April 1981
gold contracts, a “forward spread” which apparently anticipated
that interest rates would decline.

However, at the same time

Tandrill purchased January 1981 silver contracts, it sold December
1980 silver contracts, resulting in a “back spread” which sought to
profit from an increase in interest rates.
In 1979, Tandrill bought and sold 160 contracts of copper
futures straddles, 330 contracts of gold futures straddles, and
1,110 contracts of silver futures straddles through Bache.24

Of

these transactions, 164 contracts of gold futures, 721 contracts of
silver futures, and 100 contracts of copper futures were all

23

The butterfly effect offsets forward spreads (which are
profitable if interest rates decline) with back spreads (which
are profitable if interest rates increase). Mr. Maduff believes
that this sort of strategy is "economically schizophrenic".
24

Mr. Maduff believed that because Tandrill engaged in
more transactions than necessary to achieve a given economic
purpose, its transactional costs were greater. Moreover, because
Tandrill held positions for short periods of time, it was less
likely the positions would move.

-32offset, resulting in losses of approximately $1,772,000, including
commissions for 1979.25
Mr. Maduff posited that in every case, when these positions
were

first

established,

Tandrill

made

contrary

straddle

transactions in the same quantity in a different delivery month of
the same futures contract.

When these positions were closed out,

Tandrill replaced them with a like quantity of contracts in the
same futures contract but in a different delivery month, at the
same time retaining into a subsequent year the profitable positions
that had been established at the same time as these loss positions

25

The closed-out losing trades were as follows:

Source No.

Date

Quantity

Description

Loss

330011
330010
330012
330013
330014
330015
330016
330029
330019
330020
330028
330028
330029
330029

11/23/79
11/21/79
11/23/79
11/23/79
11/27/79
11/28/79
11/28/79
12/16/79
11/21/79
11/23/79
12/3/79
12/7/79
12/18/79
12/19/79

164
75
44
240
108
75
176
3
10
10
20
20
20
20

Apr. 81 gold
May 80 silver
May 80 silver
Dec. 80 silver
Mar. 81 silver
Mar. 80 silver
Sept. 80 silver
Dec. 80 silver
Mar. 80 copper
Mar. 80 copper
July 80 copper
Sept. 80 copper
July 80 copper
July 80 copper

$264,032.80
183,837.50
104,933.80
352,253.00
183,026.60
127,317.50
313,250.20
138,110.70
10,819.00
13,569.00
49,388.00
28,138.00
(612.00)
4,138.00

-33had been established.26 In sum, Mr. Maduff concluded that these
trades clearly were not motivated by the desire to make a profit.
The ACLI Trades
Tandrill did not enter into any transactions through ACLI
during 1979. Tandrill’s 1980 transactions established through ACLI

26

The following are Tandrill’s 1979 positions established
or offset, and contrary positions:
Date

Position Established or Offset

11/1/79 Sold short 18 Apr. ‘81 gold
11/6/79 Sold short 146 Apr. ‘81 gold
11/21/79 Repurchased 164 Apr. ‘81

Contrary Position

12/3/79 Repurchased 20 July ‘80 copper
12/13/79 Repurchased 20 July ‘80 copper

Bought 18 Feb. ‘81 gold
Bought 146 Feb.‘81 gold
Sold short 117 Dec.‘80 gold
Sold short 27 June ‘81 gold
Bought 119 July ‘80 silver
Sold Short 75 Mar. ‘80 silver
Sold short 44 Sept. ‘80 silver
Bought 73 Jan. ‘81 silver
Bought 79 Jan. ‘81 silver
Bought 88 Jan. ‘81 silver
Sold short 108 Mar. ‘81 silver
Sold short 132 Sept. ‘80 silver
Bought 108 Dec. ‘80 silver
Sold short 108 Dec. ‘80 silver
Bought 75 May ‘80 silver
Sold short 75 May ‘80 silver
Bought 132 Dec. ‘80 silver
Bought 44 May ‘80 silver
Sold short 132 Dec. ‘80 silver
Sold short 44 May ‘80 silver
Bought 3 Sept. ‘80 silver
Sold short 3 Mar. ‘81 silver
Bought 20 May ‘80 copper
Sold short 10 July ‘80 copper
Sold short 10 July ‘80 copper
Sold 10 Mar. ‘80 copper
Sold 10 Mar. ‘80 copper
Bought 20 May ‘80 copper
Bought 20 Sept. ‘80 copper
Sold short 20 Dec. ‘80 copper
Sold short 20 Mar. ‘80 copper

12/19/79 Repurchased 20 July ‘80 copper
11/26/79 Bought 20 Sept. ‘80 copper
12/7/79 Sold 20 Sept. ‘80 copper

Sold short 20 Mar. ‘80 copper
Sold short 20 July ‘80 copper
Bought 20 May ‘80 copper

11/15/79 Sold short 119 May ‘80 silver
11/21/79 Repurchased 119 May ‘80 silver
11/1/79 Sold short 73 Dec. ‘80 silver
11/2/79 Sold short 79 Dec. ‘80 silver
11/5/79 Sold short 88 Dec. ‘80 silver
11/21/79 Repurchased 240 Dec. ‘80 silver
11/15/79 Sold short 108 Mar. ‘81 silver
11/27/79 Repurchased 108 Mar. ‘81 silver
11/21/79 Sold short 75 Mar. ‘80 silver
11/27/79 Repurchased 75 Mar. ‘80 silver
11/21/79 Sold short 132 Sept. ‘80 silver
11/21/79 Sold short 44 Sept. ‘80 silver
11/27/79 Repurchased 176 Sept. ‘80 silver
11/27/79 Sold short 3 Dec. ‘80 silver
12/26/79 Repurchased 3 Dec. ‘80 silver
11/14/79 Sold short 20 Mar. ‘80 copper
11/21/79 Repurchased 10 Mar. ‘80 copper
11/23/79 Repurchased 10 Mar. ‘80 copper
11/21/79 Sold short 10 July ‘80 copper
11/23/79 Sold short 10 July ‘80 copper
11/26/79 Sold short 40 July ‘80 copper

-34involved futures contracts in copper, gold, 90-day Treasury bills,
sugar, GNMA’s, and 30-year U.S. Treasury bonds.27
Mr. Maduff focused on the GNMA’s and bond trades.

He opined

that the GNMA and bond28 trades appear to have been intended to roll
gains from 1980 into 1981, and in fact succeeded in rolling
$695,156.25 of gains into 1981.

In addition, because these trades

involved contracts not maturing until 1982, they had the potential
of

generating

long-term

gains

and

short-term

losses.

After

examining these transactions, Mr. Maduff concluded that these
trades did not have any profit motive or potential.
The GNMA and Treasury bond transactions were established on
June 26 and 27, 1980, with the purchase on each day of: 15 March
27

With the exception of the GNMA’s and bonds, all of the
transactions were initiated by July 1, 1980, and closed out by
Dec. 31, 1980. Thus, Mr. Maduff did not perform a detailed study
of the copper, gold, 90-day Treasury bill, or sugar transactions
because it was clear that they were not used to postpone income
recognition from one year to the next. Also, they did not have
the potential for long-term capital gains because all were closed
out in less than 6 months.
28

Treasury bond futures contracts and GNMA futures
contracts are similar instruments. Both consist of 30-year debt
instruments with a $100,000 face value and a nominal 8-percent
“coupon”. Bonds are obligations of the U.S. Government; GNMA’s
are mortgage-backed debt instruments guaranteed by an agency of
the U.S. Government. The primary difference is that, in periods
of falling interest rates, GNMA’s are subject to prepayment while
bonds are not.
In addition, these debt instruments, which on their
face provide a constant income flow for approximately 30 years,
will fluctuate in value with interest rates. However, a 3-month
spread in either bonds or GNMA’s will tend to be stable because
that spread represents only the difference between 90-day
interest rates and 30-year interest rates for a 90-day period
rather than 30-year interest rates themselves.

-351981 GNMA contracts and the simultaneous sale of 15 September 1981
GNMA contracts; and the purchase on each day of 15 September 1981
Treasury bond contracts and the simultaneous sale of 15 March 1981
Treasury bond contracts.

These transactions taken as a whole have

the appearance, and effect, of incurring minimum market exposure to
risk of loss and no possibility of net gain (after transaction
costs) notwithstanding the fact that the transactions, viewed
separately, each had the possibility of making or losing thousands
of dollars per contract.

This was accomplished by establishing

“straddles of straddles”.29
While Tandrill’s GNMA trades consisted of long March and short
September (a 6-month forward spread), the bond trades were the
opposite, short March and long September (a 6-month back spread).
Consequently, while either the GNMA straddle or bond straddle taken
29

For example, Tandrill’s bond trades of June 26 and 27,
1980, occurred as follows: In that period the price of March
GNMA’s dropped $1,062.50 per contract and the price of March
bonds dropped $1,250 per contract. At the same time the
March/September GNMA spread moved $93.75 per contract, and the
March/September bond spread moved $62.50 per contract. Finally,
the entire position taken as a whole moved the minimum possible
increment that day, $31.25 per contract.
On Oct. 28, 1980, Tandrill executed a straddle of a
straddle involving GNMA’s and bonds, buying 30 June GNMA’s and
simultaneously selling 30 March GNMA’s, and buying 30 June bonds
and simultaneously selling 30 September bonds. These
transactions resulted in recognition of a $327,030 loss on the
GNMA’s and a $368,280 loss on the bonds and still left Tandrill
with offsetting 3-month straddles, June/September GNMA’s vs.
June/March bonds. On Oct. 30, 1980, after recognizing a net loss
of $693,750 (plus commissions of $1,560), Tandrill still had
profits of $691,406.25 in its open GNMA/bond position, for a net
loss of $2,343.75 (or 2-1/2 points per contract). This loss is
primarily attributable to transaction costs.

-36in isolation would allow the investor to profit or lose based on
the relative fluctuation of long and short-term interest rates, the
two

positions

taken

together

would

result

in

virtually

no

fluctuation at all.
Mr. Maduff’s Conclusions
1.

Taken in isolation, Tandrill’s 1979 Treasury bill trading

established through Bache appears to have been taken with a profit
motive.30
2.

Tandrill’s

transactions

1979

established

gold,

silver,

and

through

Bache

were

copper
“tax

straddle

straddles”,

entered into without an objective of earning an economic profit.
3.

Tandrill’s

1980

GNMA

and

Treasury

bond

transactions

established through ACLI were “tax straddles”, entered into without
an objective of earning an economic profit.
Mr. Borst
Petitioners’ expert, Thomas J. Borst, received a B.S. in
business administration from Miami University (in Oxford, Ohio) in
1962, and an M.B.A. from the Wharton School of Commerce and Finance
at the University of Pennsylvania in 1964. After working for Inland
Steel Company and International Business Machines Corp., Mr. Borst
became an institutional and retail securities broker with several
securities firms between 1968 and 1974. Later, he began trading on
the Chicago Board Options Exchange as an independent market maker
30

Mr. Maduff asserted that he cannot “be certain” of this
conclusion because of “inadequate documentation”.

-37and then on the Chicago Board of Trade as an independent floor
trader.

He also was a principal of Frontier Limited, a commodity

trading advisory firm, and a vice president of Hedged Portfolio
Advisors, Inc., a firm that provided sophisticated tactical trading
data and advice to institutions.

Since 1991, he has traded solely

on the Chicago Board of Trade.
Mr.

Borst’s

report

and

testimony

dealt

with

Tandrill’s

Treasury bill futures contracts and Treasury bill options contracts
during the last 4 months of 1979.31 His primary conclusion was that
Tandrill’s transactions “had the potential to earn a profit”.
Treasury Bill Futures Contracts
For the period beginning September 29, 1979, Tandrill shorted
90-day Treasury bill futures contracts.

This initial strategy

reflected

interest

Tandrill’s

expectation

that

rates

would

increase.32
Treasury Bill Options Contracts
For

the

period

beginning

September

29,

1979,

Tandrill’s

Treasury bill options trading consisted of “selling” vertical put

31

In addition to his expert report, Mr. Borst prepared a
rebuttal report which briefly discussed gold and silver commodity
futures, commodity trading, and the Black-Scholes Model.
32

Short Treasury bill futures positions increase in value
as the price of Treasury bills decrease in value (when interest
rates increase). Conversely, short Treasury bill futures
positions decrease in value as the price of Treasury bills
increases (when interest rates decrease).

-38spreads and thereafter closing these positions by “buying” vertical
put spreads.33
Credit Option Spreads
Part of Tandrill’s trading strategy was to purchase Treasury
bill put options at one strike price and sell the same amount of
Treasury bill put options at a higher strike price for the same
maturity month.34
Mr. Borst provided an example of the type of credit spreads in
which Tandrill engaged. On September 20, 1979, 6 December 1979
Treasury bill futures contracts were “sold” by the trader at 90.25
and 90.26, and 11 March 1980 Treasury Bill futures contracts were
“sold” by the trader at 90.89.

Also, a total of 47 March 97.50

puts were “bought” for a total price of $1,153,991, and 47 March
97.625 puts were “sold” for $1,178,995.

The credit on the options

positions was $25,004.

33

Each option was on $1 million face value Treasury
bills; the minimum price movement was $.01 ($100). The
underlying Treasury bills’ maturity date depended upon the
expiration date of the option. The usual maturity date of the
Treasury bills was about 3 months after the expiration date of
the option.
34

The year 1979 was an extremely volatile period for
interest rates in the United States. Rates were increasing
rapidly into September 1979 and during that month. Tandrill’s
strategy in this regard provided some risk control in the event
that Treasury bill interest rates that had been increasing began
to decline. If interest rates fell, the price of the short
Treasury bill futures positions would increase, thereby creating
losses for Tandrill.

-39Because Tandrill’s options trades in the aggregate generated
a credit, its put positions could suffer an unfavorable price
movement

and

still

provide

Tandrill

with

an

overall

profit.

Further, Tandrill’s put positions provide it with the ability to
absorb some of the risk in its futures positions.

That is, the put

positions could, in the aggregate, move unfavorably by $25,004
before Tandrill suffered a net loss.

Thus, $25,004 could be used

as a cushion to absorb losses in the short futures positions (if
the price of the short futures positions increased rather than
decreased).
Tandrill’s Portfolio Trading Strategy
Tandrill’s initial trading strategy was to build a portfolio
of Treasury bill put option credit spreads and short futures
positions in Treasury bills.

During this period, Tandrill closed

some of its short commodity futures positions at a profit.

For

example, on October 3, 1979, it closed two of its short futures
contracts (December) at 88.80 and two more on October 8 at 89.90--a
profit before

commissions

of

$9,000.

Mr.

Borst

stated

that

interest rates were rising at the time Tandrill closed out its
short position, as evidenced by the fact that the closing price of
the short futures contracts in October was lower than the price of
the contracts

when

they

were

entered

into

in

September.

But

Tandrill did not simultaneously close its put positions obtained on
September 20.

Mr. Borst believed that this was understandable

-40because it was probable that the credit spread put positions would
have suffered losses in the aggregate.35
Tandrill’s Positions at September 30, 1979
At the end of September, Tandrill was short 56 Treasury bill
futures,

a

position

worth

millions

of

dollars.

Tandrill

had

partially reduced the risk of this position by selling 144 put
spreads, each

on

$1

million

worth

of

Treasury

bill

futures.

Although Tandrill received $78,000 in premiums from selling the
higher strike puts over the lower, it stood to lose $180,000 if
both ends of the spreads expired in the money, and thus could have
incurred an overall net loss of $102,000.
Despite

this

potential

loss,

Tandrill

covered

the

short

futures in early October, while actually increasing the short put
exposure.

Tandrill realized an $82,500 profit from covering its

short Decembers.
The trade also locked in an additional $100,000 to $125,000
profit on the new March-December Treasury bill futures spread. Mr.
Borst believed that Tandrill made a very bold and risky move,
switching from a very bearish position to a very bullish one.
Tandrill’s Positions at October 31, 1979
Tandrill was long December 1979 Treasury bill futures against
an equal number of the March 1980 Treasury bill futures.

35

The long

Mr. Natenberg disagreed with this analysis. He opined
that if one enters a position as a true hedge, once the primary
asset has been disposed of, the hedge is no longer required.
According to Mr. Natenberg, a true hedger would liquidate the
hedge at the time of disposition of the primary asset.

-41position was rapidly moving toward the price of the 1-year bills
whereas the

March

future

had

a

substantially

longer

time

to

expiration, so Tandrill had an opportunity to profit further on
this spread if short rates stabilized or fell.

According to Mr.

Borst, Tandrill was also well positioned with its options spreads.
Tandrill’s Trading October 31-November 15, 1979
As of November 15, 1979, Tandrill had completed the unwinding
of its credit spreads.

As short-term interest rates continued to

rise, the results were worse than anticipated.

Tandrill, however,

had approximately 150 basis points locked into its futures spread.
Thus, Tandrill “took off” some of these points by covering a part
of its short position and realized a $13,000 profit.
Tandrill’s Final Trades: November 19-December 7, 1979
Tandrill closed out its last options spread over a 5-day
period in late November.

It did not adjust its futures position

until about a week later, effectively switching its position from
bearish to bullish, as it held one extra December Treasury bill
future.

On November 28, 1979, it sold 26 December Treasury bill

futures and bought only 21 March, shifting again to an aggressively
bearish stance, as it was now short ($1 million worth) of Treasury
bill futures and held that position until December 7, 1979.
Tandrill was unable to buy the rest of its Treasury bill
futures spreads at 50 basis points, but rather, it had to pay 90
basis

points

for

21

spreads

on

November

28.

Through

its

-42speculative “legs”, however, Mr. Borst believed that Tandrill “made
the best of a deteriorating situation”. The last three spreads
Tandrill bought on December 7 resulted in its reducing its profit
further, but it was short two extra March Treasury bill futures,
which it also covered at this point at the lowest price of any
March transaction.
Conclusion
Mr. Borst opined that the aforementioned trading transactions
were

“very

positions

sophisticated”.
very

“adroitly”

Tandrill’s
in

trader

extremely

managed

volatile

instruments and a volatile financial market.

huge

financial

Mr. Borst concluded

that because Tandrill earned approximately $78,000 during a 2-1/2
month period, such fact demonstrated the high quality of Tandrill’s
trading ability, as well as the fact that Tandrill’s strategies had
the economic potential to earn a profit.
Mr. Natenberg’s Rebuttal of Mr. Borst’s Report
Mr.

Natenberg

disagreed

with

Mr.

Borst’s

conclusions.

According to Mr. Natenberg, while a trader may hedge, the fact that
he does so is not necessarily a sign of experience.

A new trader

may choose a poor hedge, either one where the trader misjudges the
amount of protection offered by the hedge, or one where the cost of
the hedge is too great relative to the protection.

Nor does the

fact that a hedge is constructed necessarily show that it was done
with the intention of earning a profit, either in the hedge or in

-43the primary asset.

In fact, Mr. Natenburg believes Tandrill paid

more for some of the option hedges than they could ever be worth.
The Relevant Law
Section 165(c)(2) provides that, in the case of an individual,
the deduction for losses set forth in section 165(a) is limited to
“losses incurred in any transaction entered into for profit, though
not connected with a trade or business”. Accordingly, in order for
Tandrill’s losses to be deductible, petitioners must establish that
the transactions
profit”.

giving

rise

to

them

were

“entered

into

for

Fox v. Commissioner, 82 T.C. 1001, 1018 (1984); Smith v.

Commissioner, 78 T.C. 350, 390 (1982).

For this purpose, “profit”

means economic profit, independent of tax savings.

Surloff v.

Commissioner, 81 T.C. 210, 233 (1983).
Section 108 of the Deficit Reduction Act of 1984, Pub. L. 98369, 98 Stat. 494, 630, as amended by section 1808(d) of the Tax
Reform Act of 1986, Pub. L. 99-514,

100 Stat. 2817, provides as

follows:
SEC. 108. TREATMENT OF CERTAIN LOSSES ON STRADDLES ENTERED
INTO BEFORE EFFECTIVE DATE OF ECONOMIC RECOVERY TAX ACT OF 1981.
(a) General Rule.--For purposes of the Internal
Revenue Code of 1954, in the case of any disposition of
1 or more positions-(1) which were entered into before 1982 and form
part of a straddle, and
(2) to which the amendments made by title V of the
Economic Recovery Tax Act of 1981 do not apply,

-44any loss from such disposition shall be allowed for the
taxable year of the disposition if such loss is incurred
in a trade or business, or if such loss is incurred in a
transaction entered into for profit though not connected
with a trade or business.
(b) Loss Incurred in a Trade or Business.--For
purposes of subsection (a), any loss incurred by a
commodities dealer in the trading of commodities shall be
treated as a loss incurred in a trade or business.
Accordingly, a taxpayer, other than a commodities dealer,36 is
not eligible to deduct a loss on the disposition of a leg in a
straddle, unless the taxpayer proves that the loss was incurred “in
a transaction entered into for profit”.

DEFRA sec. 108 as amended.

To meet this requirement the taxpayer must establish that he entered
into the straddle transaction primarily for profit.

Ewing v.

Commissioner, 91 T.C. 396, 416-417 (1988), affd. without published
opinion 940 F.2d 1534 (9th Cir. 1991); Boswell v. Commissioner, 91
T.C. 151, 158-159 (1988).

To meet the primarily-for-profit test,

the investor need not be unaware of the tax consequences that might
ensue from his transactions.

However, where an investor has a

profit motive as well as a tax motive for entering into the
investment, the profit motive must be of first importance.
Because petitioner’s investments were made through Tandrill,
the

existence

36

of

a

profit

motive

must

be

determined

at

the

Neither respondent nor petitioners contend that
petitioner or Tandrill was a commodities dealer for purposes of
the profit motive presumption of DEFRA sec. 108(b) as amended.
See Kovner v. Commissioner, 94 T.C. 893 (1990).

-45partnership level.

Rosenfeld v. Commissioner, 82 T.C. 105, 112

(1984); Brannen v. Commissioner, 78 T.C. 471, 505 (1982), affd. 722
F.2d 695 (11th Cir. 1984); Hager v. Commissioner, 76 T.C. 759, 784
(1981).

A

partnership’s

profit

motivation

is

determined

by

reference to the actions of the general partners who manage the
affairs of the partnership.

See Resnik v. Commissioner, 66 T.C. 74

(1976), affd. per curiam 555 F.2d 634 (7th Cir. 1977).
In Ewing v. Commissioner, supra at 417-418, it was established
that profit must be the taxpayer’s primary motive in order for a
loss from a particular straddle transaction to be deductible.

In

Ewing we also set forth the following additional guidelines, taken
from Fox v. Commissioner, 82 T.C. 1001 (1984):
(1) The ultimate issue is profit motive and not
profit potential.
However, profit potential is a
relevant factor to be considered in determining profit
motive. 82 T.C. at 1021.
(2) Profit motive refers to economic
independent of tax savings. 82 T.C. at 1022.

profit

(3) The determination of profit motive must be made
with reference to the spread positions of the straddle
and not merely to the losing legs, since it is the
overall scheme which determines the deductibility or
nondeductibility of the loss. 82 T.C. at 1018, citing
Smith v. Commissioner, 78 T.C. at 390-391.
(4) If there are two or more motives, it must be
determined which is primary, or of first importance. The
determination is essentially factual, and greater weight
is to be given to objective facts than to self-serving
statements characterizing intent. 82 T.C. at 1022.
(5) Because the statute speaks of motive in
“entering” a transaction, the main focus must be at the

-46time the transactions were initiated. However, all
circumstances surrounding the transactions are material
to the question of intent. 82 T.C. at 1022. [Ewing v.
Commissioner, supra at 417-418]
Petitioners contend that Tandrill’s primary purpose in entering
into the transactions at issue was to further its profit-making
objectives. Respondent, on the other hand, argues that Tandrill did
not enter into these transactions primarily for profit.

Respondent

further contends that the most important factor determining profit
is the trading pattern involved.

Each party relies on its expert’s

analysis of Tandrill’s trading.
Tandrill’s Trading Activities Were Not Profit Motivated
We have considered the qualifications and experience of the
parties’ experts and their particular knowledge and experience in
options and futures transactions, as well as the substance and
reasoning of their reports.

We found respondent’s expert witness

reports and testimony more useful and persuasive than that of
petitioner’s. Messrs. Natenberg’s and Maduff’s reports support our
conclusion that tax considerations primarily motivated Tandrill’s
trading.37

37

Mr. Maduff concluded that Tandrill’s 1979 Treasury bill
trading established through Bache appears to have been taken with
a profit motive. We therefore assume that respondent concedes
that these trades were taken with a profit motive. Thus, the
following discussion does not address Tandrill’s 1979 Treasury
bill trading established through Bache.

-47a. Tandrill Paid More than Fair Value When Purchasing Option
Spreads and Received Less than Fair Value When Selling Option
Spreads
Tandrill’s

put

option

spreads

resulted

in

losses

solely

because: (1) With regard to the credit spreads, Tandrill received
less than fair value when it initiated the spreads and paid more
than fair value when it closed out such spreads; and (2) with regard
to the debit spreads, Tandrill received less than fair value when
it closed out the spreads.
The option spreads (unlike the futures transactions) were not
executed on a regulated exchange.

They were over-the-counter

transactions executed through Pershing and Arbitrage Management.
Thus, there was no active trading market to assure a fair price to
all traders.

Further, there was no institutional safeguard to

prevent Pershing or Arbitrage Management from charging Tandrill more
(or paying Tandrill less) than some other trader for an identical
position.
There is no evidence in the record that Tandrill bargained with
Pershing

or

Arbitrage

Management,

or

engaged

in

“comparison

shopping”, to insure that it received fair prices, even though there
were three or four dealers that made a market in over-the-counter
Treasury bill options.

Mr. Illingworth did not instruct Messrs.

Willensky and Sherman of Wilcap (who placed the actual trades) to
attempt to get the best price they could for the option spreads, nor

-48did he otherwise discuss with them the prices they were getting for
the spreads.
Moreover, even though in 1979 options traders generally relied
upon the Black-Scholes theoretical pricing model, Mr. Illingworth
was unaware of the model.
usage

of

the

Even in the absence of Mr. Illingworth’s

Black-Scholes

theoretical

pricing

model,

Mr.

Illingworth should have known that Tandrill was systematically
receiving far less than fair value for the spreads it was selling.38
Such transactions result from a systematic disregard of economic
values in executing option spread transactions.39
38

For example, when Tandrill closed out its credit
spreads, in each case it paid more for the closing spread than
its maximum theoretical value.
39

Respondent claims that Fox v. Commissioner, 82 T.C.
1001 (1984), is factually similar to this case. Respondent
posits that Tandrill’s option spreads were similar to the 1977
series of transactions in Fox in that both were initiated and
closed out in the same year and over a relatively short period of
time.
In Fox all the transactions were executed through
Arbitrage Management. Like Tandrill’s two option spread
transactions executed through Arbitrage Management (but unlike
the six such transactions executed through Pershing), the spreads
in Fox were debit and bearish spreads. Id. at 1003. Also, the
taxpayers in Fox and Tandrill each sustained economic losses.
Id. at 1004.
Further, the tax strategy used by the taxpayer in Fox
was very similar to the strategy Tandrill followed. The taxpayer
in Fox reported ordinary losses and short-term capital gains for
the years in issue, treating the dispositions of individual legs
of the spreads as separate taxable events. Because Treasury
bills were at that time specifically excluded from the definition
of a capital asset by sec. 1221(5), the taxpayer reported the
losses as ordinary losses. This Court upheld the deficiency,
holding that the taxpayer did not enter into the transactions
(continued...)

-49b.

Tandrill’s Futures Transactions Were Not Profit Motivated

Tandrill’s 1979 gold, silver, and copper futures transactions
and the 1980 Treasury bond and GNMA futures transactions were
entered into for the purpose of deferring income from one tax year
to the next, and generating approximately equal amounts of shortterm capital loss and long-term capital gain. The futures straddles
were designed to minimize the volatility of the straddle as a whole,
yet produce substantial losses in one leg of the straddle (and
offsetting gain in the other leg).
the gain deferred.

The loss was then realized, and

In Tandrill’s straddles, the opportunity for

profit and risk of loss was minimized by keeping the spreads in
effect for short periods of time, putting on spreads with short
intervals between delivery dates, and maximizing the butterfly
effect.40
39

(...continued)
primarily for profit and that the transactions were not a type of
tax-motivated transaction that Congress intended to encourage.
Petitioners attempt to distinguish Fox on the grounds
that the taxpayer in Fox: (1) Did not engage in any Treasury bill
futures trading; (2) conducted all the trading in “isolated yearend transactions” that were “unquestionably tax motivated”; and
(3) had entered into the options transactions only after both he
and his accountant had “thoroughly investigated their potential
tax benefits.”
We agree with respondent that the two options spreads
Tandrill initiated through Arbitrage Management were similar to
the spreads in Fox.
40

More specifically, Tandrill’s commodity futures trading
was used to defer income from 1979 into 1980 in the case of the
gold, silver, and copper straddles cleared through Bache, and
from 1980 into 1981 in the case of the Treasury bond and GNMA
(continued...)

-50This strategy reduced Tandrill’s overall potential for economic
profit or loss, but substantially increased its transactional costs.
We are convinced that Tandrill’s primary aim was to generate tax
benefits.
The tax-motivated nature of Tandrill’s futures straddles is
reflected in the timing of the transactions that closed out its
losses.

For example, in 1979 the loss legs of the precious metals

straddles were closed out on dates of large price movements in the
underlying metals.41

The record indicates that in November 1979,

traders closed out their short silver positions and simultaneously
replaced

them

with

other

short

silver

positions.

The

sole

motivation of this strategy was to lock in a tax loss for 1979 and
to push the corresponding gain into 1980.
Tandrill did.

This is precisely what

Of the 721 silver contracts that it closed out in

1979, 718 were closed out either on November 21, 1979, or November
27, 1979, landmark dates for large price movements.

40

(...continued)
futures straddles cleared through ACLI.
41

For instance, in November 1979, the price of silver
futures fluctuated far more than normal. This meant that for
traders holding silver spreads, both long and short legs
increased sharply in value, placing the long leg in a position
with a substantial profit and the short leg in a position with a
substantial loss. For tax-motivated individuals, this was the
optimal occasion to close out the loss leg, realizing the loss
for tax purposes, and to replace that position with another short
position comprising the same number of silver contracts
(typically with a delivery date late in 1980).

-51c.

Tandrill’s Overall Tax Strategy

The purpose of Tandrill’s investment strategy was to generate
losses from the loss legs of its Treasury bill option spreads that
would be deductible by petitioners as ordinary losses in 1979 and
to generate a corresponding (though somewhat smaller) amount of gain
from the profit legs of the option spreads that would be taxable as
short-term capital gains.

From its futures straddles, Tandrill’s

purpose was to generate short-term capital losses in 1979 that would
offset the short-term capital gains generated by the Treasury bill
options transactions, and to defer the recognition of gain from the
profit legs of such commodity futures straddles until a subsequent
year.

The gain was carried forward into 1980 and realized as long-

term capital gain.

A similar approach was used to defer capital-

gain income from 1980 into 1981.

Such strategy was employed to

produce in substance an economic loss on a long-term basis.
We agree with respondent that Tandrill’s options transactions
employed a character-mismatching strategy similar to the 1977
options spreads in Fox v. Commissioner, 82 T.C. 1001 (1984).

The

loss on the loss leg of each option spread would be an ordinary
loss; the profit on the gain leg would be a short-term capital gain.
The ordinary losses Tandrill reported on its Form 1065 for 1979
arose from Treasury bill options transactions (and, to a minor
extent, from deductions for management and accounting fees).

The

losses

to

from

Treasury

bill

transactions

for

1979

amounted

$1,858,743 and arose from purchased put options that were closed out

-52at a loss in 1979.

Because the losses were on purchased puts, they

purportedly qualified for ordinary loss treatment under section
1234.42
The $163,666 in net short-term capital gain Tandrill reported
for 1979 represents the excess of its short-term capital gains of
$1,736,366

over

its

short-term

capital

losses

of

$1,572,700.

Tandrill realized its short-term capital gains on put options on
Treasury bills and the short-term capital losses from the loss legs
of futures straddles on gold, silver, copper, and Treasury bills.43
Tandrill’s $1,509,077 of long-term capital gain for 1980 resulted
from the closing out of Tandrill’s commodity futures straddles.
We are convinced that Tandrill’s overall trading strategy was
geared toward the assurance of tax savings for its partners rather
than a real profit motive.

See, e.g., Leslie v. Commissioner, T.C.

Memo.

with

1996-86

transactions).

(dealing

profit

motive

in

gold

And profit motive is the crucial test.

futures

See, e.g.,

Fox v. Commissioner, supra at 1021.

42

Sec. 1234(a)(1) provides that the character of the gain
or loss on the sale or exchange of a purchased option is the same
as the character of the gain or loss on the sale of the property
to which the option relates. Because Treasury bills were at that
time specifically excluded from the definition of a capital asset
by sec. 1221(5), Tandrill reported the losses as ordinary losses.
43

Under sec. 1234(b), the character of the gain or loss
recognized on the closing out of granted options is short-term
capital gain or loss.

-53Petitioner and Mr. Illingworth
Both petitioner and Mr. Illingworth testified that they did not
discuss the tax ramifications of creating and operating Tandrill.
Under the circumstances herein, we are not required to, and we do
not, accept the self-serving testimonial evidence presented by
petitioners

to

sustain

their

burden

of

establishing

error

in

respondent’s determination.44 See Geiger v. Commissioner, 440 F.2d
688, 689-690 (9th Cir. 1971), affg. per curiam T.C. Memo. 1969-159.
Based upon the entire record, we conclude that petitioner
became a partner in Tandrill in order to reap tax benefits; i.e.,
to offset the $3,492,989 gain he realized in 1976 from the sale of
his Hy-Gain stock with losses from Tandrill.

The record makes it

clear that petitioner, Mr. Illingworth, and Tandrill all had the
same primary objective: to create tax losses.

The absence of a

primary for-profit objective is “so obvious that it must be the same
for all of the individual partners or their [partnership].” Donahue
v. Commissioner, T.C. Memo. 1991-181, affd. without published
opinion 959 F.2d 234 (6th Cir. 1992).

Thus, it makes no practical

difference whether the relevant motive belongs to petitioner, Mr.
Illingworth, or Tandrill itself.
Petitioner willingly accepted the Partnership and Management
Agreements.

He contributed $300,000 for a 93.75-percent interest;

Mr. Illingworth contributed $20,000 for a 6.25-percent interest.

44

Petitioner’s testimony was marked by frequent failures
of recall, and he failed to provide answers to simple questions.

-54However, Tandrill paid Mr. Illingworth’s company, Manhattan Metals,
$10,000 (denominated as a retainer and organization fee) upon the
signing

of

the

Management

Agreement.

Thus,

in

essence,

Mr.

Illingworth’s net contribution was approximately $10,000.
In addition, in 1980 Manhattan Metals received a $50,000
management fee (and $25,000 annually thereafter), plus an incentive
payment that would be triggered if the net assets of Tandrill
increased

beyond

a

stipulated

annual

percentage

threshold.

Manhattan Metals also had the right to share in the brokerage
commissions and other fees Tandrill paid.
Petitioner’s $300,000 investment was a fraction of the tax
benefits that Tandrill’s transactions were expected to provide.
Petitioners’ total deficiencies of $986,305 for 1976 and 1980
(arising from the disallowance of Tandrill’s losses) represent a
claimed tax benefit of more than three times his investment in
Tandrill. We believe that petitioner agreed to the arrangement with
Mr. Illingworth and Manhattan Metals because tax savings, rather
than Tandrill’s economic performance, was petitioner’s primary
objective.
Petitioner was a prototypical “passive investor”.
have a meaningful role in Tandrill’s management.

He did not

Tandrill only

engaged in trading activities, and these activities were delegated
to Manhattan Metals (and hence effectively to Mr. Illingworth) by
means of the Management Agreement. Petitioner testified that he did
not understand Tandrill’s trading activities. Although he claims to

-55have invested in Tandrill in order to earn a profit, we believe that
petitioner chose to invest in an area in which he had little
background in order to realize tax benefits.
Petitioner was financially sophisticated.

His tax advisers at

Peak Marwick gave him “an education” on the anticipated tax benefits
of Tandrill’s trading.

They informed him that the tax consequences

of his investment in Tandrill “could be advantageous.”

It is clear

that petitioner expected the tax losses that Tandrill generated.
Moreover,

petitioner

expected

to

carry

back

losses

from

Tandrill 3 years. See sec. 172(b)(1)(A). Tandrill began operations
in 1979, and that year petitioner carried his Tandrill losses back
to 1976, the year in which he reported a gain of almost $3.5 million
from the sale of Hy-Gain stock and an adjusted gross income of
$2,047,797.

Petitioners’ tax liability for 1976 was $1,355,566.

Thus, as a result of investing in Tandrill, petitioners were
expecting to carry back a net operating loss into 1976.

This

carryback would reduce their tax liability by $1,053,742. This
reduction, more than any supposed profit potential, was petitioner’s
real motive.
Mr. Illingworth was the “brains” behind Tandrill’s trading
activities.

While he clearly understood the nature of Tandrill’s

options

futures

and

transactions,

he

delegated

considerable portion of the decision making.45

45

at

least

a

Concurrently, Mr.

Mr. Illingworth’s precise role in Tandrill’s trading
(continued...)

-56Illingworth was involved with other partnerships that realized tax
losses in all years for which their results are in evidence.
partnerships had similar trading patterns to Tandrill.

The

This is

another indication that Mr. Illingworth’s “expertise” as a trader
lay in his ability to produce tax losses for his partners.
Conclusion
We conclude that Tandrill did not enter into the options and
futures transactions with a primary profit motive. Thus, respondent
properly disallowed petitioners’ allocable share of Tandrill’s 1979
and 1980 losses under section 165(c)(2).
Issue 2.
The

Section 6653(a) Additions to Tax
second

issue

is

whether

petitioners

are

liable

for

additions to tax for negligence or intentional disregard of rules
or regulations for 1976 and 1980.

For these years, respondent has

the burden of proving petitioners’ negligence or disregard of rules
and regulations because it is a new matter raised in respondent’s
amended answer.

45

Rule 142(a).

(...continued)
activities is unclear. As president of Manhattan Metals, he had
ultimate responsibility for Tandrill’s trading. However, the
extent to which Mr. Illingworth personally determined which
trades Tandrill should make, what trading strategies Tandrill
should adopt, or the degree of his oversight is uncertain. For
example, he apparently delegated all responsibility for the
options trading to Messrs. Willensky and Sherman of Wilcap
Advisors, and for the futures trading to Mr. Weiss, a Manhattan
Metals employee. And Mr. Illingworth testified that Mr. Weiss
did not discuss his trades with Mr. Illingworth.

-57Section 6653(a) for 1976 and 1980 imposes an addition to tax
if any part of an underpayment of tax is due to negligence or
intentional disregard of rules or regulations.

Negligence is the

lack of due care or failure to do what a reasonable and ordinarily
prudent

person

would

do

under

the

circumstances.

Neely

v.

Commissioner, 85 T.C. 934, 947 (1985).
Based upon the record before us, we conclude that respondent
has not satisfied her burden of proof on this issue.

Thus,

petitioners are not liable for the section 6653(a) additions to tax
for 1976 and 1980.
Issue 3.
The

Section 6621(c) Additional Interest
third

issue

is

whether

petitioners

additional interest for 1976 and 1980.

are

liable

for

Respondent determined that

petitioners are liable for the increased rate of interest provided
in section 6621(c) (formerly section 6621(d)).

Respondent has the

burden of proof on this issue with regard to 1976 (because it is a
new matter raised in respondent’s amended answer) and petitioners
have the burden of proof with regard to 1980.
Section 6621(c) provides for an interest rate on substantial
underpayments attributable to tax-motivated transactions that is
120 percent of the underpayment rate provided in section 6601. See
Stanley Works & Subs. v. Commissioner, 87 T.C. 389, 413-415 (1986).
Section 6621(c) applies to interest accrued after December 31, 1984,
even though the transaction was entered into prior to the date of
enactment of section 6621(c). Solowiejczyk v. Commissioner, 85 T.C.

-58552, 555-557 (1985), affd. without published opinion 795 F.2d 1005
(2d Cir. 1986).
$1,000.

An underpayment is substantial if it exceeds

Sec. 6621(c)(2).

The phrase “tax-motivated transactions”

includes straddles and transactions lacking a profit motive.

See

Ewing v. Commissioner, 91 T.C. at 422-423.
We have concluded that petitioner and Mr. Illingworth formed
Tandrill for the purpose of generating tax benefits.

Moreover, the

$1,000 statutory threshold is surpassed in this case for both
taxable years in issue.

Consequently, petitioners’ underpayments

based on the losses attributable to tax-motivated transactions are
subject to the additional interest provided by section 6621(c).

We

hold that petitioners are liable for the increased rate of interest
under section 6621(c) on the entire underpayments for 1976 and 1980.
To reflect the foregoing,
Decision will be
entered under Rule 155.

-59APPENDIX A
TANDRILL'S 1979 PURCHASES OF PUT OPTION POSITIONS THROUGH
PERSHING AND BY THE CORRESPONDING SALES OF SUCH POSITIONS
In all of the transactions below, the expiration date for the
option was December 5, 1979, and the expiration date of the
underlying Treasury bill was March 4, 1980.

Purchases

Sales

Date

No.

Yield

Cost

Date

No.

Proceeds

9/20

47

97.50

$1,153,991

11/7
11/8

33
14

$ 544,731
225,498

11/7
11/8
9/24

33
14
41

97.625
97.625
97.53

586,905
243,404
941,196

9/20
11/12
11/13
11/14
11/15

47
20
6
7
8

1,178,995
280,600
82,044
92,785
99,640

11/12
11/13
11/14
11/15
9/25
11/9
9/26

20
6
7
8
40
40
16

97.65
97.65
97.65
97.65
97.53
97.65
97.50

305,220
89,436
101,402
109,496
902,320
659,840
354,128

9/24
11/9
9/25
11/9
11/12
11/13

41
40
40
8
4
4

962,721
610,640
924,280
119,752
54,928
53,508

11/9
11/12
11/13
10/2

8
4
4
26

97.625
97.625
97.625
97.45

129,984
60,052
58,628
516,282

9/26
11/9
11/12
11/15

16
11
10
5

363,968
159,203
132,360
58,300

11/9
11/12
11/15
10/3
11/14

11
10
5
8
8

97.51
97.51
97.51
97.45
97.51

166,188
138,720
61,480
158,344
104,768

10/2
11/14
10/3

26
8
8

523,120
99,680
160,520

-60APPENDIX B
TANDRILL'S 1979 PURCHASES OF PUT OPTION POSITIONS THROUGH
ARBITRAGE MANAGEMENT AND THE CORRESPONDING SALES OF SUCH
POSITIONS
In all of the transactions below, the expiration date for the
option was March 26, 1980, and the expiration date of the underlying
Treasury bill was June 24, 1980.
Purchases

Sales

Date

No.

Yield

Cost

Date

No.

Proceeds

10/30

25

97.16

$1,464,975

11/20
11/21
11/23

13
10
2

$632,476
488,170
96,562

11/20
11/21
11/23
10/31
11/19

13
10
2
24
24

97.08
97.08
97.08
97.16
97.08

629,408
485,470
96,162
1,389,744
1,185,192

10/30
11/19
10/31

25
24
24

1,454,325
1,191,360
1,380,192

-61APPENDIX C
TANDRILL'S 1979 PUT OPTION SPREAD TRANSACTIONS THROUGH PERSHING
AND ARBITRAGE MANAGEMENT
In all of the transactions below, the expiration date for the
option was December 5, 1979, and the issuance date of the underlying
Treasury bill was March 4, 1980.
Trade
Date

Type

No.

Trade

Commission

Cash Flow

47
47

97.50
97.625

$940
940

$(1,153,991)
1,178,995
25,004

33
33

97.50
97.625

660
660

544,731
(586,905)

Opening Trade:
9/20

Bought
Sold

Closing Trades:
11/7

Sold
Bought

(42,174)
11/8

Sold
Bought

14
14

97.50
97.625

280
280

225,498
(243,404)
(17,906)

Opening Trade:
9/24

Bought
Sold

41
41

97.53
97.65

820
820

(941,196)
962,721
21,525

Closing Trades:
11/12

Sold
Bought

20
20

97.53
97.65

400
400

280,600
(305,220)
( 24,620)

11/13

Sold
Bought

6
6

97.53
97.65

120
120

82,044
(89,436)
( 7,392)

11/14

Sold
Bought

7
7

97.53
97.65

140
140

92,785
(101,402)
( 8,617)

-6211/15

Sold
Bought

8
8

97.53
97.65

160
160

99,640
(109,469)
( 9,856)

40
40

97.53
97.65

800
800

(902,320)
924,280
21,960

40
40

97.53
97.65

800
800

610,640
(659,840)
( 49,200)

16
16

97.50
97.625

320
320

(354,128)
363,968
9,840

Opening Trade:
9/25

Bought
Sold

Closing Trade:
11/9

Sold
Bought

Opening Trade:
9/26

Bought
Sold

Closing Trades:
11/9

Sold
Bought

8
8

97.50
97.625

160
160

119,752
(129,984)
( 10,232)

11/12

Sold
Bought

4
4

97.50
97.625

80
80

54,928
(60,052)
( 5,124)

11/13

Sold
Bought

4
4

97.50
97.625

80
80

53,508
(58,628)
( 5,120)

_____________________________________________________________
Opening Trade:
10/2

Bought
Sold

26
26

97.45
97.51

520
520

(516,282)
523,129
6,838

Closing Trades:
11/9

Sold
Bought

8
8

97.50
97.625

160
160

159,203
(166,188)
( 6,985)

11/12

Sold
Bought

4
4

97.50
97.625

80
80

132,360
(138,720)

-63(
11/13

Sold
Bought

6,360)

4
4

97.50
97.625

80
80

58,300
(61,480)
( 3,180)

8
8

97.45
97.51

160
160

(158,344)
160,520
2,176

8
8

97.45
97.51

160
160

99,680
(104,768)
( 5,088)

Opening Trade:
10/3

Bought
Sold

Closing Trade:
11/4

Sold
Bought

-64APPENDIX D
TANDRILL'S 1979 PUT OPTION SPREAD TRANSACTIONS
THROUGH ARBITRAGE MANAGEMENT
In all of the transactions below, the expiration date for the
option was March 26, 1980, and the issuance date of the underlying
Treasury bill was June 24, 1980.
Trade
Date

Type

No.

Trade

Commission

Cash Flow

25
25

97.16
97.08

500
500

$(1,464,975)
1,454,325
(
10,650)

Opening Trade:
10/30

Bought
Sold

Closing Trades:
11/20

Sold
Bought

13
13

97.16
97.08

260
260

632,736
(629,148)
3,588

11/21

Sold
Bought

10
10

97.16
97.08

200
200

488,370
(485,270)
3,100

11/23

Sold
Bought

2
2

97.16
97.08

40
40

96,602
(96,122)
480

24
24

97.16
97.08

480
480

(1,389,744)
1,380,192
(
9,552)

24
24

97.16
97.08

480
480

1,191,840
(1,184,712)
7,128

Opening Trade:
10/31

Bought
Sold

Closing Trade:
11/19

Sold
Bought

-65APPENDIX E
TRADE ANALYSIS

DATE

TRADE
TYPE

TRADE

DAYS TO
EXPIRATION

UNDERLYING
PRICE

INTEREST
RATE

SPREAD
PRICE

MAXIMUM
SPREAD VALUE

SPREAD
VALUE RANGE

9/20/79

Spread +47 97.50P
Sale
-47 97.625P

76

97.45

10.21

25,004

58,750

32,638-50,553

9/24/79

Spread +41 97.53P
Sale
-41 97.65P

72

97.50

10.02

21,525

49,200

26,786-41,143

9/25/79

Spread +40 97.53P
Sale-4097.65P

71

97.48

10.08

21,960

49,200

26,744-41,508

9/26/79

Spread +16 97.50P
Sale
-16 97.625P

70

97.45

10.21

9,840

20,000

11,184-17,399

10/2/79

Spread +26 97.45P
Sale
-26 97.51P

64

97.41

10.38

6,838

15,600

8,357-12,246

10/3/79

Spread + 8 97.45P
Sale
- 8 97.51P

63

97.40

10.40

2,176

4,800

2,605-3,928

11/7/79

Spread -33 97.50P
Purchase +33 97.625P

28

96.88

12.50

42,174

41,250

38,976-40,856

11/8/79

Spread -14 97.50P
Purchase +14 97.625P

27

96.89

12.45

17,906

17,500

16,551-17,340

11/9/79

Spread -40 97.53P
Purchase +40 97.65P

26

97.01

11.98

49,200

48,000

44,316-47,592

11/9/79

Spread - 8 97.50P
Purchase + 8 97.625P

26

97.01

11.98

10,232

10,000

9,135-9,915

11/9/79

Spread -11 97.45P
Purchase +11 97.51P

26

97.01

11.98

6,985

6,600

5,800-6,544

11/12/79 Spread -20 97.53P
Purchase +20 97.65P

23

97.00

12.00

24,620

24,000

22,526-23,819

11/12/79 Spread - 4 97.50P
Purchase + 4 97.625P

23

97.00

12.00

5,120

5,000

4,649-4,962

11/12/79 Spread -10 97.45P
Purchase +10 97.51P

23

97.00

12.00

6,360

6,000

5,389-5,955

11/13/79 Spread - 6 97.53P
Purchase + 6 97.65P

22

97.00

12.00

7,392

7,200

6,787-7,148

11/13/79 Spread - 4 97.50P
Purchase + 4 97.625P

22

97.00

12.00

5,120

5,000

4,671-4,964

11/14/79 Spread - 7 97.53P
Purchase + 7 97.65P

21

96.95

12.20

8,617

8,400

8,055-8,341

11/14/79 Spread - 8 97.45P
Purchase + 8 97.51P

21

96.95

12.20

5,088

4,800

4,457-4,766

11/15/79 Spread - 8 97.53P
Purchase + 8 97.65P

20

97.08

11.70

9,856

9,600

8,884-9,539

11/15/79 Spread - 5 97.45P
Purchase + 5 97.51P

20

97.00

12.00

3,180

3,000

2,710-2,978

10/30/79 Spread +25 97.16P
Purchase -25 97.08P

148

96.99

12.06

10,650

20,000

10,603-16,178

10/31/79 Spread +24 97.16P
Purchase -24 97.08P

147

96.96

12.15

9,552

19,200

10,422-16,439

-66APPENDIX E
(Continued)
TRADE ANALYSIS

DATE

TRADE
TYPE

TRADE

DAYS TO
EXPIRATION

UNDERLYING
PRICE

INTEREST
RATE

SPREAD
PRICE

MAXIMUM
SPREAD VALUE

SPREAD
VALUE RANGE

11/19/79

Spread -24 97.16P
Sale
+24 97.08P

128

97.02

11.93

6,168

19,200

10,066-14,791

11/20/79

Spread -13 97.16P
Sale
+13 97.08P

127

97.01

11.95

3,068

10,400

5,503-8,249

11/21/79

Spread -10 97.16P
Sale
+10 97.08P

126

97.08

11.68

2,700

8,000

3,980-4,873

11/23/79

Spread - 2 97.16P
Sale
+ 2 97.08P

124

97.16

11.35

400

1,600

747-562

---

Source: Frix Law Library, https://www.frixlaw.com/law-library/documents/agency%3Atax-court%3A2ae044ad03ae630e. Public record. Not legal advice.