United States v. Bryant, Thomas

In the

United States Court of Appeals

For the Seventh Circuit

No. 07-3608

U NITED S TATES OF A MERICA,

Plaintiff-Appellee,

v.

T HOMAS B RYANT,

Defendant-Appellant.

Appeal from the United States District Court

for the Northern District of Illinois, Eastern Division.

No. 05 CR 71—Elaine E. Bucklo, Judge.

A RGUED O CTOBER 21, 2008—D ECIDED F EBRUARY 26, 2009

Before R IPPLE, E VANS and SYKES, Circuit Judges.

R IPPLE, Circuit Judge. On April 8, 2005, Thomas Bryant

provided Eddie Franklin with a substance containing

cocaine base. Franklin delivered that substance to a

confidential informant, who then turned the sample over

to the Government. Mr. Bryant was subsequently

arrested and charged with one count of conspiracy to

distribute cocaine base. Mr. Bryant initially pleaded

guilty to the charge, but later unsuccessfully sought to

withdraw his guilty plea. At his sentencing hearing, the

2 No. 07-3608

district court sentenced Mr. Bryant to 180 months’ impris-

onment. Mr. Bryant now challenges the district court’s

denial of his motion to withdraw his guilty plea. He

also raises several challenges to the sentence imposed by

the district court. For the reasons set forth in this opinion,

we affirm the district court’s denial of his motion to

withdraw his plea, vacate his sentence and remand for

resentencing.

I

BACKGROUND

A.

In 2005, a confidential informant contacted Eddie Frank-

lin and attempted to purchase crack cocaine. Franklin

agreed to obtain crack for the informant and called the

defendant, Thomas Bryant, in an attempt to procure the

drugs. On April 8, 2005, Mr. Bryant provided Franklin

with a substance that Franklin described as hard and rock-

like. Franklin then delivered the substance to the infor-

mant, who turned it over to Drug Enforcement Adminis-

tration (“DEA”) agents.

A DEA chemist analyzed the substance and, in his report,

described it as a beige, compressed, moist powder. Al-

though the substance tested positive for the presence of

cocaine base, the chemist did not detect the presence of

No. 07-3608 3

sodium bicarbonate in the substance.1 Later, a second

DEA chemist analyzed the substance, described it as

hard and rock-like and concluded that it contained

sodium bicarbonate. After the second chemist completed

his analysis, the Government discovered that he had

mishandled evidence on several occasions during the

time period in which he analyzed the substance at issue

here. The Government decided that, because chain of

custody issues may have resulted from the chemist’s

mishandling of evidence, it would introduce neither the

substance nor the second chemist’s report in its case

against Mr. Bryant.

B.

Several months after Franklin delivered the substance

to the informant, the Government arrested Mr. Bryant and

Franklin. Mr. Bryant subsequently entered a blind condi-

tional guilty plea to one count of conspiracy to distribute

cocaine base; he reserved the issues of the type and quan-

tity of the drugs involved for a bench trial. At the time

of his plea, he was aware that the first DEA chemist’s

description of the substance conflicted with Franklin’s

description. He believed, however, that the second DEA

chemist’s report would corroborate Franklin’s description

1

The presence of sodium bicarbonate in a mixture containing

cocaine base is one of the indicators that the mixture is crack

cocaine.

4 No. 07-3608

of the substance.2 At the time of his plea, Mr. Bryant was

unaware that the second chemist had mishandled evi-

dence.

On October 27, 2006, Mr. Bryant moved to withdraw

his plea. He claimed that he had been pressured into

accepting the plea by his former attorney, who had

stated that he was unprepared for trial. Mr. Bryant did not

claim that he was innocent of the crime charged; rather,

he indicated that he did not believe that the Govern-

ment could prove its case beyond a reasonable doubt.

The district court held a plea withdrawal hearing, during

which both Mr. Bryant and his former attorney testified.

The district court noted that Mr. Bryant’s statements

conflicted with his former attorney’s statements. It con-

cluded that Mr. Bryant had intentionally misled the

court and denied Mr. Bryant’s motion to withdraw his

plea.

Mr. Bryant asserts that, immediately prior to his

bench trial, he made a second motion to withdraw his

plea on the basis of newly discovered evidence.3 He con-

2

The first DEA chemist to analyze the substance described it

as a beige, compressed, moist powder. Both the second DEA

chemist and Franklin described the substance as hard and rock-

like.

3

The Government contends that Mr. Bryant did not move to

withdraw his plea; rather, it claims, he requested additional

time “to figure it out and determine whether it matters.” R.183-9

at 6. The Government characterizes Mr. Bryant’s statements

(continued...)

No. 07-3608 5

tended that he should be allowed to withdraw his plea

on the ground of newly discovered evidence in light of the

Government’s discovery that the second chemist had

mishandled evidence and its decision that it would not

introduce the substance or the second DEA chemist’s

report. The district court rejected this argument. It con-

cluded that Mr. Bryant would not have altered his

decision had he known that the second chemist mishan-

dled evidence because Mr. Bryant “necessarily challenged

[the chemist’s] finding by saying he wasn’t going to

agree that it was crack.” R.183-9 at 17.

On August 3, 2007, the district court held a bench trial

to determine the type and quantity of drugs involved in

the conspiracy.4 Franklin testified that he had purchased

3

(...continued)

as an emergency motion to continue the bench trial. Statements

made by the district court support this characterization. R.183-9

at 18 (“I’m not going to continue [the trial], not for that rea-

son.”).

Although Mr. Bryant claims to have made a motion to

withdraw his plea, there is no indication that he expressly

requested that his plea be withdrawn. Nevertheless, because

Mr. Bryant asserted that he should have “known about [the

evidentiary problems] so [he] could have figured this out

while [he] still had time,” id. at 6, we shall assume, for the

purposes of this appeal, that Mr. Bryant moved to withdraw

his plea.

4

The issue of the type and quantity of drugs involved in the

charged crime was litigated on two occasions in the pro-

ceedings before the district court: First, in order to determine

(continued...)

6 No. 07-3608

crack from Mr. Bryant on numerous occasions. He re-

counted the details of the April 8 transaction, stating that

he received about sixty-three grams of crack cocaine

from Mr. Bryant. He described the substance he received

4

(...continued)

the statutory maximum sentence, the court held a bench trial to

determine whether the Government had proven, beyond a

reasonable doubt, that Mr. Bryant had conspired to distribute

five kilograms or more of a mixture containing cocaine or fifty

grams or more of a mixture containing cocaine base. 21 U.S.C.

§ 846 (“Any person who attempts or conspires to commit any

offense defined in this subchapter shall be subject to the same

penalties as those prescribed for the offense, the commission

of which was the object of the attempt or conspiracy.”); 21

U.S.C. §§ 841(b)(1)(A)-(C) (establishing statutory maximum

and minimum sentences for the crime of possession with

intent to distribute a controlled substance). As we previously

have noted, “all facts . . . that set the maximum possible punish-

ment under § 841(b) must be established beyond a reasonable

doubt to the satisfaction of the same body that determines

culpability under § 841(a).” United States v. Brough, 243

F.3d 1078, 1079 (7th Cir. 2001) (citing United States v. Nance, 236

F.3d 820 (7th Cir. 2000)). Next, the district court held a sentenc-

ing hearing to determine the type and quantity of the drugs

involved in the charged conspiracy; at that hearing, “[t]he

government [had] the burden of proving the quantity of drugs

attributable to [the] defendant for sentencing purposes by a

preponderance of the evidence.” United States v. Krasinski,

545 F.3d 546, 551 (7th Cir. 2008) (citing United States v. Soto-

Piedra, 525 F.3d 527, 529 (7th Cir. 2008)).

No. 07-3608 7

on that date as hard and rock-like.5 The district court

concluded, based on the discrepancy between the first

DEA chemist’s description of the substance and

Franklin’s description of the substance, that the Govern-

ment had failed to prove, beyond a reasonable doubt, that

Mr. Bryant had conspired to distribute crack cocaine.

R.144.

At Mr. Bryant’s sentencing hearing, the district court

found, based on the testimony presented at the bench

trial, 6 that the Government had proven, by a preponderance

of the evidence, that Mr. Bryant had conspired to

distribute more than fifty grams of crack cocaine. The

court therefore assigned Mr. Bryant a base offense level

of 30 under the November 2007 Amendments to the

Sentencing Guidelines.7 The district court next applied a

two-level enhancement for obstruction of justice based

5

Although Franklin could recall the details of the April 8

transaction with specificity, he was unable to provide specific

information about the amounts of drugs involved in any of his

prior transactions with Mr. Bryant or the dates on which

those transactions took place. Nor could he estimate the num-

ber of times he had purchased drugs from Mr. Bryant.

6

The Government presented no new evidence at the sen-

tencing hearing.

7

Although the November 2007 Amendments were not in

effect at the time Mr. Bryant was sentenced, the district court

agreed, pursuant to Mr. Bryant’s request, to sentence him

under the November 2007 Amendments. The November 2007

Amendments partially ameliorated the sentencing disparity

between crack and powder cocaine.

8 No. 07-3608

on its finding that Mr. Bryant intentionally had made

material misrepresentations to the court during his first

plea withdrawal hearing. It then denied Mr. Bryant’s

motion for a two-level reduction in offense level for

acceptance of responsibility. As a result of these enhance-

ments, the court determined that Mr. Bryant’s offense

level was 32.

Next, the district court assigned a criminal history

category of IV to Mr. Bryant, based, in part, upon a state-

court conviction for cocaine possession. Mr. Bryant

claimed, however, that the conviction should not be

considered for the purpose of determining his criminal

history category; instead, he submitted, the conviction

should be considered relevant conduct for sentencing

purposes because the conviction involved similar

conduct that had taken place during the time period of

the conspiracy. The district court declined to deem the

conviction relevant conduct.

The district court sentenced Mr. Bryant to 180 months’

imprisonment, a sentence in the middle of the advisory

guideline range for an individual of Mr. Bryant’s criminal

history category and offense level. Because Mr. Bryant

was sentenced before the Supreme Court’s decision in

Kimbrough v. United States, ___ U.S. ___, 128 S. Ct. 558

(2007), the district court did not take the sentencing

disparity between crack and powder cocaine into

account when determining Mr. Bryant’s sentence.

Mr. Bryant subsequently filed this appeal.

No. 07-3608 9

II

DISCUSSION

Mr. Bryant raises the following arguments: (1) the

district court abused its discretion in denying his second

motion to withdraw his plea; (2) the district court clearly

erred in finding that the Government had proven, by a

preponderance of the evidence, that the charged con-

spiracy involved crack cocaine; (3) the district court

clearly erred in applying a two-level enhancement for

obstruction of justice based on the statements he made

at his first plea withdrawal hearing; (4) the district court

clearly erred in declining to apply a two-level reduction

for acceptance of responsibility; (5) the district court

clearly erred by increasing his criminal history score

because of his state-court conviction for possession of

cocaine base; and (6) his sentence should be vacated

and remanded for resentencing in light of the Supreme

Court’s opinion in Kimbrough, 128 S. Ct. 558. We shall

address each of these arguments in turn.

A.

Mr. Bryant contends that the district court erred in

denying his second motion to withdraw his guilty plea.

We review a district court’s denial of a motion to with-

draw a plea for abuse of discretion. United States v. Silva,

122 F.3d 412, 414-15 (7th Cir. 1997). After a district court

accepts a defendant’s guilty plea and before it imposes

a sentence, the court may permit the defendant to with-

draw his plea provided that he “can show a fair and

10 No. 07-3608

just reason for requesting the withdrawal.” Fed. R.

Crim. P. 11(d)(2)(B); accord United States v. Underwood, 174

F.3d 850, 852 (7th Cir. 1999). The defendant bears the

burden of proving that a fair and just reason for with-

drawal exists. United States v. Coonce, 961 F.2d 1268, 1275

(7th Cir. 1992).

Mr. Bryant claims that, immediately prior to his bench

trial, he discovered new evidence that undermined the

Government’s case against him: He learned that the

second DEA chemist had mishandled drug samples

during the time period in which he evaluated the sub-

stance at issue in Mr. Bryant’s case, and that the Gov-

ernment no longer intended to introduce the second

chemist’s report or the substance itself into evidence.

Mr. Bryant contends that because he discovered new,

relevant evidence after entering his plea, see, e.g., United

States v. Garcia, 401 F.3d 1008, 1011 (9th Cir. 2005), and

because the discovery of that evidence enabled him to

make a legal argument that he was unaware of at the time

of his plea, see, e.g., United States v. Groll, 992 F.2d 755, 759-

60 (7th Cir. 1993), he has demonstrated a fair and just

reason to withdraw his plea.

We cannot say that the district court abused its discre-

tion in denying this motion. Unlike the defendant in

Garcia, Mr. Bryant did not present newly discovered

evidence relating to his factual guilt or innocence. Garcia,

401 F.3d at 1011-12 (concluding that the defendant’s

discovery of a new witness created a fair and just reason

for withdrawal of the defendant’s guilty plea because the

witness’ statement “raise[d] new questions about [the

No. 07-3608 11

defendant’s] involvement in the illegal activity”). Addi-

tionally, unlike the defendant in Groll, Mr. Bryant did not

introduce evidence that, at the time of his plea, he was

unaware of a legal defense to the crime charged. Groll, 992

F.2d at 758, 759-60 (stating that “being legally innocent of

the crime is a fair and just reason to withdraw a guilty

plea” and concluding that the district court abused its

discretion in denying the defendant’s motion to with-

draw her guilty plea when unrebutted evidence in the

record could have supported her entrapment defense

and the defendant may have been unaware of the en-

trapment defense at the time she pleaded guilty).

The evidence and legal arguments that Mr. Bryant relied

upon in his motion at best relate to the strength of the

Government’s case against him, not his factual or legal

innocence. As we previously have noted, “[a] defendant

is not entitled to withdraw his plea merely because he

has misapprehended the strength of the government’s

case.” Silva, 122 F.3d at 415. When a defendant has been

apprised of the facts giving rise to the charges against

him, the mere fact that he does not know, at the time of

his plea, what evidence the Government will use against

him does not present a “fair and just” reason for him to

withdraw his plea. See Underwood, 174 F.3d at 853-54

(concluding that “[the defendant’s] reevaluation of his

trial prospects afforded no basis for withdrawing his

validly-entered guilty pleas”); United States v. Seybold, 979

F.2d 582, 587 (7th Cir. 1992) (noting that Rule 11 “does not

require the trial judge at the plea hearing to air all of the

government’s evidence”). Furthermore, it is far from

clear that Mr. Bryant’s discovery of the problem with one

12 No. 07-3608

of the Government’s chemists would have impacted his

decision to plead guilty. Although Mr. Bryant pleaded

guilty to the charged conspiracy, he specifically reserved

for a bench trial the issues of the type and quantity of

drugs involved in the conspiracy. In other words, he

admitted to conspiring to possess and distribute drugs;

he did not admit that the drugs he conspired to distrib-

ute included cocaine or cocaine base. The discovery of

the chemist’s mishandling of the evidence, however,

relates solely to the issue of the type of drugs involved in

the conspiracy, and is irrelevant to the question of whether

Mr. Bryant conspired to distribute any controlled sub-

stance. As the district court noted, Mr. Bryant “necessarily

challenged [the second chemist’s] finding by saying he

wasn’t going to agree that [the substance] was crack.”

R.183-9 at 17. We therefore cannot say that the district

court abused its discretion in rejecting Mr. Bryant’s

motion to withdraw his plea.

B.

1.

Mr. Bryant raises a number of challenges to the sen-

tence imposed by the district court. Among his other

arguments, Mr. Bryant contends, and the Government

concedes, that his sentence should be vacated and re-

manded in light of the Supreme Court’s decision in

Kimbrough v. United States, ___ U.S. ___, 128 S. Ct. 558

(2007). We agree with the parties that Mr. Bryant

preserved this issue. During the sentencing hearing,

which was held before the Supreme Court’s decision in

No. 07-3608 13

Kimbrough, Mr. Bryant maintained that the drugs involved

in the conspiracy were not crack cocaine. As we held in

United States v. Padilla, 520 F.3d 766, 774 (7th Cir. 2008),

such a position is sufficient to preserve the Kimbrough

issue. Accordingly, we vacate Mr. Bryant’s sentence and

remand for resentencing so that the district court may

take into account the sentencing disparity between crack

and powder cocaine when sentencing Mr. Bryant. We

now turn to the remainder of Mr. Bryant’s challenges to

his sentence.

2.

Mr. Bryant challenges the district court’s conclusion

that the charged conspiracy involved crack cocaine. We

review the district court’s finding for clear error, United

States v. Wilson, 437 F.3d 616, 621 (7th Cir. 2006), and shall

reverse its decision “only if we are left with the definite

and firm conviction that a mistake was made.” Padilla,

520 F.3d at 769.

The Government was required to prove, by a prepon-

derance of the evidence, that the charged conspiracy

involved “crack” cocaine. United States v. Johnson, 200

F.3d 529, 537 (2000). Mr. Bryant claims that the Govern-

ment’s evidence on this issue, which consisted solely of

the evidence presented at the bench trial, was insufficient

to support the district court’s finding. In particular,

Mr. Bryant claims that Franklin’s testimony was unreli-

able because, with the exception of the April 8 transaction,

Franklin was unable to recall the details of any of the

transactions in which he allegedly received crack cocaine

14 No. 07-3608

from Mr. Bryant. Mr. Bryant describes Franklin’s testi-

mony as an allegation “that, at some point in the past,

though he doesn’t remember exactly when, [Franklin]

received some amount of crack cocaine [from Mr. Bryant],

though he doesn’t remember how much,” and asserts

that this vague testimony cannot support a finding that

Mr. Bryant conspired to distribute more than fifty grams

of crack cocaine. Appellant’s Br. 28.

Although Franklin’s testimony lacked specific details

about the transactions in which he had obtained crack

cocaine, it nevertheless contained sufficient details to

support the district court’s conclusion. Franklin was not

able to recall the dates on which he received crack cocaine

from Mr. Bryant or the specific quantities of crack cocaine

he received. However, he did testify that each of the

transactions involved more than sixty-three grams of

crack cocaine. In addition, he provided detailed testi-

mony about an occasion when he watched Mr. Bryant

“cook” powder cocaine into crack cocaine. Further-

more, Franklin’s testimony was not the only evidence

presented to the district court on this issue; the Govern-

ment introduced recorded conversations between

Franklin and the informant, in which those two

individuals discussed having Franklin’s supplier “cook”

the cocaine. It also introduced evidence that the sub-

stance that Franklin received on April 8 contained cocaine

base. The district court was entitled to rely on this evi-

dence, in its totality, in determining that the conspiracy

involved crack cocaine. See, e.g., Padilla, 520 F.3d at 770-71

(noting that “the government can prove a substance is

crack by offering testimony from people familiar with the

No. 07-3608 15

drug, United States v. Anderson, 450 F.3d 294, 301 (7th Cir.

2006), including . . . an informant’s belief that he was

purchasing crack”); United States v. Earnest, 185 F.3d 808,

813 (7th Cir. 1999) (recognizing that a court may rely on

the testimony of experts and other witnesses in con-

cluding that a substance is crack cocaine).

Mr. Bryant also suggests that, because the Government

could not show that the substance contained sodium

bicarbonate, it failed to prove, by a preponderance of the

evidence, that the substance was crack cocaine. The

Sentencing Guidelines distinguish between “cocaine base”

and “cocaine” for sentencing purposes. U.S.S.G. § 2D1.1(c)

(“Drug Quantity Table”). Although “greater punishment

applies to cocaine base than to cocaine,” Lemon v. United

States, 335 F.3d 1095, 1095 (8th Cir. 2003), the Sentencing

Guidelines did not define “cocaine base” until the Guide-

lines were amended in 1993. United States v. Waters, 313

F.3d 151, 155 (3d Cir. 2002). “Prior to 1993, circuit courts

were divided over whether ‘cocaine base’ under § 2D1.1

included only ‘crack,’ or whether it also broadly encom-

passed all other substances the scientific community

generally considered to be cocaine base.” United States v.

Abdul, 122 F.3d 477, 478 (7th Cir. 1997) (citations omitted)

(discussing the conflicting definitions of cocaine base

adopted by various courts). To resolve the conflict, the

Sentencing Commission proposed an amendment to

Section 2D1.1(c). Id. The amendment, which became

effective in 1993, id. at 479, reads as follows:

“Cocaine base,” for the purposes of [the Sentencing

Guidelines], means “crack.” “Crack” is the street name

16 No. 07-3608

for a form of cocaine base, usually prepared by pro-

cessing cocaine hydrochloride and sodium bicarbonate,

and usually appearing in a lumpy, rocklike form.

U.S.S.G. § 2D1.1(c) note (D) (hereinafter “Note D”).8

Although “the definition of ‘cocaine base’ in the Guide-

lines makes it clear that only the ‘crack’ form of cocaine

base should receive the . . . sentencing enhancement

under § 2D1.1,” United States v. Jones, 159 F.3d 969, 982

(6th Cir. 1998), the Guidelines do not explicitly define

“crack” in terms of its chemical composition, method of

manufacture or physical appearance. See Waters, 313

F.3d at 156 (noting that “there is no precise chemical

definition of crack cocaine,” and concluding that “crack

generally refers more to the way the drug is prepared

and used than the specific chemical composition”).

Perhaps due to the reference to sodium bicarbonate in

Note D and the absence of a specific definition of “crack,”

it has become common for individuals sentenced under

Section 2D1.1 to challenge whether a substance is, in

fact, crack cocaine. Often, as in the case before this

court, these challenges take the form of claims that the

substance at issue cannot be crack cocaine because it

does not contain sodium bicarbonate. See, e.g., Abdul, 122

F.3d at 478. We have rejected this argument. We have

8

“Notes or commentary to the sentencing guidelines are

considered binding authority unless either violative of the

Constitution or a federal statute, or clearly inconsistent with

the guideline[s].” United States v. Brooks, 161 F.3d 1240, 1248

(10th Cir. 1998) (internal quotation marks and citations omitted).

No. 07-3608 17

held that, based on the use of the qualifying term “usu-

ally” in Note D, “crack” is not limited to cocaine that has

been processed with sodium bicarbonate. See id. at 479

(“If courts were to disregard the qualifying term ‘usually,’

crack dealers could avoid the penalties for distribution

of crack by merely finding some substitute for baking

soda in production, or by crushing the rocks so that

the final product resembles powder.”). Other courts

have reached similar conclusions. See United States v.

Whitehead, 487 F.3d 1068, 1072 (8th Cir. 2007) (“[T]he

government need not show the presence of sodium bicar-

bonate in order to prove that cocaine is crack. . . .”);

United States v. Eli, 379 F.3d 1016, 1022 (D.C. Cir. 2004)

(“The Sentencing Guidelines do not insist that crack can

be made only with sodium bicarbonate; they merely

state that it is ‘usually prepared’ that way.” (internal

citation omitted)); Waters, 313 F.3d at 155 (“[I]t is not

necessary for the government to show that a substance

contains sodium bicarbonate in order to demonstrate by

a preponderance of the evidence that the drugs in ques-

tion are crack cocaine.”); United States v. Brooks, 161 F.3d

1240, 1248 (10th Cir. 1998) (“We interpret the qualifier

‘usually’ . . . as an acknowledgment that other methods

of crack preparation exist and that not all forms of

‘cocaine base’ need contain sodium bicarbonate to

qualify as crack for sentencing purposes. Indeed, it

appears that the method which uses sodium bicarbonate

is the least sophisticated and yields the lowest purity.”

(internal quotation marks and citations omitted)); Jones,

159 F.3d at 983 (“[T]he presence of sodium bicarbonate

is not a necessary prerequisite to a district court’s

factual determination that cocaine base is crack.”).

18 No. 07-3608

Our approach takes into account the fact that there are

multiple methods of manufacturing crack cocaine. Indeed,

we have stated expressly that “while crack might gen-

erally be produced using sodium bicarbonate, production

with sodium bicarbonate is not the exclusive preparation

method recognized for the purposes of § 2D1.1(c).” Abdul,

122 F.3d at 479. Two of our sister circuits have

recognized that chemical compounds other than sodium

bicarbonate, including sodium borate and niacinamide,

may be used to convert powder cocaine into crack cocaine.9

Furthermore, at least one expert has opined that, even

where sodium bicarbonate is utilized to process powder

cocaine into crack, the final product may not necessarily

contain detectable quantities of sodium bicarbonate.

Waters, 313 F.3d at 153 (referring to the statements of a

DEA chemist who testified as follows: “If the conversion

9

United States v. Eli, 379 F.3d 1016, 1022 (D.C. Cir. 2004)

(holding that the district court did not clearly err in

“conclud[ing] that the presence of sodium borate did not

undermine the conclusion that the substance was crack,” based,

in part, on an expert’s testimony that he: (1) had converted

powder cocaine to crack using sodium borate; (2) had previously

detected sodium borate in other crack samples; and (3) was

aware that other chemists had detected sodium borate in

crack samples); United States v. Waters, 313 F.3d 151, 156-57

(3d Cir. 2002) (noting an officer’s testimony that “niacinamide

is commonly used in the Philadelphia area as a substitute

for sodium bicarbonate,” and concluding that the district court

did not err in finding that the substance at issue was crack

cocaine).

No. 07-3608 19

is performed properly and you use the correct amounts

of sodium bicarbonate and powdered cocaine . . . you

should have no sodium bicarbonate left when the con-

version is complete. However, traditionally, what we

find is that out on the street an excess of this bicarbonate

is used in the conversion.” (internal quotation marks and

citations omitted)).

Cases from this and other circuits establish, therefore,

that the presence of sodium bicarbonate is not a litmus test

for establishing that a substance is “crack” for the pur-

poses of Section 2D1.1. Instead, courts have considered

the following factors, among others, in determining

whether a substance qualifies as crack for sentencing

purposes: (1) whether “the substance at issue [has] tested

positive for the presence of cocaine base”;1 0 (2) the color

of the substance;11 (3) the shape and texture of the sub-

stance;12 (4) the method of packaging;1 3 (5) the price of the

10

United States v. Brown, 499 F.3d 817, 824 (8th Cir. 2007); see

also Brooks, 161 F.3d at 1247, 1248-49; United States v. Canales,

91 F.3d 363, 368 (2d Cir. 1996) (concluding that the Guidelines

were not ambiguous as applied to the defendant because,

among other things, DEA reports indicated that the substance

tested positive for the presence of cocaine base).

11

United States v. Morris, 498 F.3d 634, 644 (7th Cir. 2007)

(“yellowish-white” substance); Canales, 91 F.3d at 368 (white

substance).

12

Morris, 498 F.3d at 644 (noting that “[o]ther evidence corrobo-

rated the fact that the drugs in question were crack cocaine,” in-

cluding a DEA agent’s testimony that “ ‘the material . . . was

(continued...)

20 No. 07-3608

substance; and (6) whether the seller represents the

substance as or understands the substance to be crack.1 4

Indeed, a comprehensive analysis that focuses on not

only the chemical composition of a substance but also its

appearance and other properties, its packaging, and the

representations associated with its sale is consistent

with the congressional concerns that prompted the statu-

tory sentencing disparity: crack’s low cost, high availabil-

12

(...continued)

kind of wet, which is not uncommon for crack’ ”); Brown,

499 F.3d at 824 (“rock” form); Canales, 91 F.3d at 368 (“chunky”

substance).

13

Morris, 498 F.3d at 644 (noting that testimony “describ[ing] the

usual method for packaging crack” and indicating that the

“drugs that were recovered were ‘packaged for distribution’ as

crack cocaine” supported the district court’s conclusion that “the

drugs in question were crack cocaine and not some other

form of cocaine base”).

14

Eli, 379 F.3d at 1021 n.7 (declining to decide whether the

Government must prove that the substance would pass for

crack on the streets, but concluding that, if such a require-

ment did exist, the requirement would be satisfied by the

defendant’s admission that the substance was crack and “by the

fact that [the defendant] sold the drugs as ‘crack’ to an under-

cover officer”); Canales, 91 F.3d at 368 (“The street name ‘crack’

is not ambiguous, because crack has a common and ordinary

meaning that is understood by [the defendant] . . . by others

in the drug trade, and by citizens in communities that are

plagued by the drug.”).

No. 07-3608 21

ity and quick, intense high.1 5 See also United States v. Scott,

No. 08-2579, slip op. at 10 (7th Cir. Feb. 11, 2009) (“There

are special dangers posed to society when cocaine is

marketed in a form that makes it more readily available

to a wider and more vulnerable part of our population.”).

Crack is not defined merely by its secondary ingredients;

it is a “product,” particularly dangerous because of its

ability to reach a wide, susceptible market and produce,

in that market, disastrous effects for both those who

fall prey to its addictive allure and the people who come

in contact with them.

Considering the concerns that gave rise to the sen-

tencing disparity, we conclude that district courts may

15

Although there is little legislative history discussing the

reasoning behind the sentencing disparity between crack and

powder cocaine, Congress’ concern for the impact that crack

would have on individuals and communities is clear. See, e.g.,

132 Cong. Rec. 26,447 (1986) (statement of Sen. Chiles) (“The

whole Nation now knows about crack cocaine. They know it

can be [bought] for the price of a cassette tape, and make

people into slaves.”); 132 Cong. Rec. 19,241 (1986) (statement of

Sen. Chiles) (“Crack is available to the young, and it will be in

the schools this fall. . . . We have all heard of cocaine, but I must

stress to you that crack cocaine is something altogether dif-

ferent. It is more powerful; it is cheaper to use; it is also far

more addictive. Crack cocaine is a purified form of powdered

cocaine that is smoked. A hit of crack costs around $10, well

within the budget of any teenager. When smoked, crack reaches

the brain in less than 10 seconds. It produces a short but

incredibly powerful high that is followed by an equally power-

ful low.”).

22 No. 07-3608

rely on a number of factors, including those we have

discussed, in determining whether a substance is crack. We

restate our earlier conclusion that the Government need

not prove that a substance contains sodium bicarbonate

in order to establish, for the purposes of Section 2D1.1, that

a substance is crack. Accordingly, we cannot say that

the district court clearly erred in determining that

Mr. Bryant conspired to distribute more than fifty grams

of crack cocaine.

3.

The district court concluded that Mr. Bryant made

material misrepresentations during his first plea with-

drawal hearing, in which he claimed that he was pres-

sured into pleading guilty and that his former attorney

told him that he was unprepared for trial. Therefore, the

district court imposed a two-level enhancement for ob-

struction of justice under Section 3C1.1 of the Sentencing

Guidelines. U.S.S.G. § 3C1.1. We review for clear error

the district court’s factual finding underlying the decision

to impose the enhancement. United States v. Griffin,

310 F.3d 1017, 1022 (7th Cir. 2002).

An obstruction of justice enhancement may be imposed

when a defendant has “willfully obstructed or impeded, or

attempted to obstruct or impede, the administration of

justice with respect to the investigation, prosecution, or

sentencing of the instant offense of conviction.” U.S.S.G.

§ 3C1.1. The obstructive conduct must be related to the

“offense of conviction and any relevant conduct” or a

“closely related offense.” Id. “Committing, suborning, or

No. 07-3608 23

attempting to suborn perjury supports an obstruction

enhancement.” Griffin, 310 F.3d at 1023 (citing U.S.S.G.

§ 3C1.1 cmt. n.4(b)). “In order to find obstruction based

on perjury, the sentencing court must find that the defen-

dant willfully made misrepresentations under oath that

were relevant to the prosecution, and specifically in-

tended to obstruct justice.” United States v. Carroll, 412

F.3d 787, 793 (7th Cir. 2005) (citing United States v.

Dunnigan, 507 U.S. 87, 94 (1993)).

Mr. Bryant claims that the Government failed to demon-

strate that he made false representations with the intent

to obstruct justice. Although he admits that the state-

ments he made at the plea withdrawal hearing conflicted

with his former attorney’s testimony, he claims that the

statements were an honest, though perhaps inaccurate,

recollection of his discussions with his attorney. He

asserts that his statements were not the result of a specific

intent to obstruct justice, but, rather, were the product

of his own misunderstanding and faulty memory.

The district court explicitly addressed the willfulness of

Mr. Bryant’s statements. It rejected his claim that he

lacked specific intent to mislead the court:

It wasn’t that . . . [Mr. Bryant] perceived that [his

attorney] wasn’t prepared. The statements under oath

were that Mr. Willis told him he had to plead

guilty. . . . [T]here was nothing there about perception.

It was actual statements.

R.183-11 at 3. The district court concluded, based on its

observation of Mr. Bryant and his former attorney—the

24 No. 07-3608

only witnesses to testify at the plea withdrawal hear-

ing—that Mr. Bryant “lied in his testimony.” R.183-8 at 12.

The district court was entitled to make this conclusion. The

district court simply based its determination that

Mr. Bryant had perjured himself on its evaluation of the

sworn statements of Mr. Bryant and his former attorney.

We cannot say that the court clearly erred in reaching

its conclusion.

4.

The district court also determined that Mr. Bryant was

not entitled to a two-level reduction for acceptance of

responsibility. The Guidelines permit district courts to

apply a two-level reduction when a defendant “clearly

demonstrates acceptance of responsibility for his offense.”

U.S.S.G. § 3E1.1(a). The district court concluded, based

on Mr. Bryant’s statements at his first plea withdrawal

hearing, that Mr. Bryant was not entitled to the two-

level reduction.

The Government submits that the district court’s con-

clusion was correct; it notes that conduct resulting in an

obstruction of justice enhancement “ordinarily indicates

that the defendant has not accepted responsibility for his

criminal conduct.” U.S.S.G. § 3E1.1 cmt. n.4.1 6 In the Gov-

16

Accord United States v. Martinez, 169 F.3d 1049, 1056 (7th Cir.

1999) (“Where a defendant falsely denies [ ] relevant conduct

that the court determines to be true, he has acted in a manner

(continued...)

No. 07-3608 25

ernment’s view, this is not the type of extraordinary case

where both an obstruction of justice enhancement and

an acceptance of responsibility reduction are warranted.

On the basis of this record, the district court reasonably

could have determined that Mr. Bryant had not accepted

responsibility for his conduct. Nevertheless, a statement

made by the district court in the course of its proceedings

gives us pause: The district court indicated that, because

of Mr. Bryant’s statements at his first plea withdrawal

hearing, “there was obstruction, and, you know, it was [a]

very foolish thing to do because legally that means

there’s no acceptance of responsibility.” R.183-8 at 13.

However, the district court later recognized that “there

are exceptions where somebody may have obstructed

justice and could be allowed to accept responsibility.”

R.183-11 at 6.

It is clear that, while a finding that a defendant ob-

structed justice “ordinarily indicates that the defendant

has not accepted responsibility for his criminal conduct,”

U.S.S.G. § 3E1.1 cmt. n.4 (emphasis added), the ap-

plication of an obstruction of justice enhancement does not

necessitate the denial of a reduction in offense level for

acceptance of responsibility. See, e.g., United States v. Davis,

442 F.3d 1003, 1009-10 (7th Cir. 2006) (“A defendant

whose sentence was properly enhanced for obstruction

16

(...continued)

inconsistent with the acceptance of responsibility, and the

district court may refuse to grant this reduction.” (internal

citations and quotation marks omitted)).

26 No. 07-3608

of justice is presumed not to have accepted responsibil-

ity. . . . It is only under exceptional circumstances that a

defendant who has received a sentence enhancement for

obstruction of justice will be given a downward adjust-

ment for acceptance [of] responsibility.” (internal citations

omitted)). Because we remand Mr. Bryant’s sentence on

other grounds, we need not determine whether the

district court clearly erred in denying Mr. Bryant an

acceptance of responsibility adjustment. The district

court will have the opportunity to revisit this issue on

remand.

5.

The parties agree that, during the relevant time period,

Mr. Bryant pleaded guilty in Illinois state court to simple

possession of less than fifteen grams of cocaine. At his

sentencing hearing, Mr. Bryant argued that the state-

court conviction should not be considered when calculat-

ing his criminal history category; instead, he maintained

that it should be considered as relevant conduct for

sentencing purposes, because the conduct giving rise to

the conviction involved possession of distribution-level

quantities of cocaine during the conspiratorial time

period. In the district court, the Government disagreed

with Mr. Bryant’s contention: It asserted that the state-

court conviction should not be considered relevant

conduct because Mr. Bryant pleaded guilty to mere

possession of, and not distribution of, cocaine. The Gov-

ernment also claimed that there was insufficient evidence

for the court to find that the conduct underlying the

No. 07-3608 27

conviction was related to the charged conspiracy. In its

argument, the Government suggested that the court

could not use the information in the police reports and

charging documents to determine whether the state-

court conviction should be considered relevant conduct.

R.183-11 at 10. On appeal, however, the Government now

concedes that “the district court could have found that

the . . . state case constituted relevant conduct.” Govern-

ment’s Br. 35.

The district court rejected Mr. Bryant’s claim that the

conviction should be considered relevant conduct, con-

cluding that it “[did not] have enough information to

say that [the conviction was] part of th[e] conspiracy.”

R.183-11 at 15. Consequently, the court assigned Mr.

Bryant a criminal history level of IV.1 7

When calculating a defendant’s criminal history cate-

gory, a district court may not consider prior convictions

for acts which constitute relevant conduct—conduct that

was part of the instant offense. U.S.S.G. § 4A1.2 cmt. n.1.

Whether a prior conviction may be considered relevant

conduct depends on the acts which gave rise to the con-

viction; as we have noted, the name of the offense to which

a defendant pleaded guilty “cannot be the basis of the

district court’s [relevant conduct] determination, for . . .

the sentencing guidelines direct courts to look to the

underlying conduct of the offense, and not the name of

17

The parties agree that, had the conviction been considered

relevant conduct, Mr. Bryant would have been assigned a

criminal history category of III.

28 No. 07-3608

the offense itself, when assessing relevant conduct.”

United States v. Olson, 408 F.3d 366, 374 (7th Cir. 2005)

(instructing the district court to determine whether the

defendant “possessed the drugs [involved in his plea to

possession of a controlled substance] merely for his

personal use, or with an intent to distribute”) (citing

United States v. Garecht, 183 F.3d 671, 674 (7th Cir. 1999) and

United States v. Wyss, 147 F.3d 631, 632 (7th Cir. 1998)). See

U.S.S.G. §§ 4A1.2, 4A1.2 cmt. n.1 (noting that, for the

purpose of computing the defendant’s criminal history

level, a “prior sentence [is] any sentence . . . for conduct not

part of the instant offense,” as specified in Section 1B1.3

(emphasis added)); U.S.S.G. § 1B1.3(a)(2) (stating that

relevant conduct includes “all acts and omissions . . . that

were part of the same course of conduct or common

scheme or plan as the offense of conviction” (emphasis

added)). Therefore, the district court must consider the

acts giving rise to Mr. Bryant’s state-court conviction and

evaluate whether those acts and the charged conspiracy

were either “part of a single episode, spree, or ongoing

series of offenses,” or “substantially connected to each

other by . . . [a] common factor, such as common victims,

common accomplices, common purpose, or similar

modus operandi.” U.S.S.G. § 1B1.3 cmt. n.9. Where the

conduct underlying a prior conviction is unclear, the

district court must “make specific factual findings re-

garding the underlying conduct . . . thereby clearly pro-

viding the basis for its ultimate resolution of the

relevant conduct question.” Olson, 408 F.3d at 374.

We cannot tell, based on the record before us, whether

the district court ultimately concluded that it could not

No. 07-3608 29

consider the underlying police reports and charging

documents in its relevant-conduct analysis. Certain

statements indicate that the district court believed that

it could consider only the conduct to which Mr. Bryant

ultimately pleaded guilty in its relevant-conduct analysis.1 8

Other statements, however, indicate that the district

court simply did not have enough information to deter-

mine whether the conduct underlying the conviction

was relevant to the charged conspiracy.1 9 On remand, the

district court will have the opportunity to further explain

its reasoning and to conduct any fact-finding necessary

to resolve this issue.

Conclusion

In sum, we hold that the evidence of the DEA chemist’s

mishandling of evidence related solely to the strength of

the Government’s case and did not present a fair and

just reason for Mr. Bryant to withdraw his guilty plea.

Therefore, the district court did not abuse its discretion

in rejecting Mr. Bryant’s motion to withdraw his guilty

plea. Furthermore, we conclude that the district court

appropriately addressed the issues of whether the

18

See, e.g., R.183-11 at 14-15 (“I think if the government tried

to say this was delivery of a controlled substance, you would

be well within your rights to come back and say, ‘Wait a

minute. He pled guilty to possession, and that’s all you can

do,’ so if it made a difference.”).

19

See, e.g., R.183-11 at 15 (“I don’t have enough information to

say that it is part of this conspiracy. . . .”).

30 No. 07-3608

charged conspiracy involved crack cocaine and whether

an obstruction of justice enhancement was appropriate.

Nevertheless, we vacate Mr. Bryant’s sentence and remand

for resentencing so that the district court may take into

account the sentencing disparity between crack and

powder cocaine when sentencing Mr. Bryant. On

remand, the district court will also have the opportunity to

address fully whether Mr. Bryant is entitled to an accep-

tance of responsibility adjustment and whether Mr.

Bryant’s state-court conviction for possession of cocaine

constitutes relevant conduct for sentencing purposes.

Therefore, Mr. Bryant’s conviction is affirmed, but his

sentence is vacated and his case is remanded to the

district court for resentencing.

A FFIRMED in part, V ACATED

and R EMANDED in part

2-26-09