United States v. Phillip Howard

USCA11 Case: 23-13871 Document: 76-1 Date Filed: 01/07/2026 Page: 1 of 18

NOT FOR PUBLICATION

In the

United States Court of Appeals

For the Eleventh Circuit

____________________

No. 23-13871

Non-Argument Calendar

____________________

UNITED STATES OF AMERICA,

Plaintiff-Appellee,

versus

PHILLIP TIMOTHY HOWARD,

Defendant- Appellant.

____________________

Appeal from the United States District Court

for the Northern District of Florida

D.C. Docket No. 4:22-cr-00043-AW-MAL-1

____________________

____________________

No. 24-10042

Non-Argument Calendar

____________________

UNITED STATES OF AMERICA,

Plaintiff-Appellee,

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2 Opinion of the Court 23-13871

versus

PHILLIP T. HOWARD,

Defendant-Appellant.

____________________

Appeal from the United States District Court

for the Northern District of Florida

D.C. Docket No. 4:22-cr-00043-AW-MAL-1

____________________

Before NEWSOM, ABUDU, and ANDERSON, Circuit Judges.

PER CURIAM:

Phillip Howard appeals both his conviction and sentence re-

sulting from his guilty plea to racketeering in violation of 18 U.S.C.

§ 1962(c). He argues that his guilty plea was invalid because it was

not supported by a sufficient factual basis and because it was not

knowing and voluntary. He further argues that his 168-months’

imprisonment sentence is both procedurally and substantively un-

reasonable. He asserts that the district court improperly calculated

his sentence because it used relevant conduct to which he did not

plead guilty and inaccurate calculations of actual loss to determine

his offense level. Howard also argues that the district court erred

in imposing restitution in an amount equal to actual loss, and that

it erred in imposing a forfeiture money judgment in the amount of

$10,651,941.40. For the reasons we’ll explain below, we AFFIRM

the district court on all grounds.

The facts of the case are known to the parties, and we repeat

them here only as necessary to decide the case.

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23-13871 Opinion of the Court 3

I

A

When, as here, a defendant fails to challenge the validity of

a guilty plea in the district court, we review for plain error. United

States v. Puentes-Hurtado, 794 F.3d 1278, 1285 (11th Cir. 2015). The

defendant bears the burden of showing “that (1) there is an error;

(2) the error is clear or obvious, rather than subject to reasonable

dispute; (3) the error affected [his] substantial rights; and (4) the er-

ror seriously affects the fairness, integrity or public reputation of

judicial proceedings.” United States v. Hill, 119 F.4th 862, 866 (11th

Cir. 2024) (quotation omitted).

A district court must determine that there is a factual basis

for a guilty plea before accepting it. Fed. R. Crim. P. 11(b)(3).

Whether the facts were sufficient to support the plea depends upon

“whether the trial court was presented with evidence from which

it could reasonably find that the defendant was guilty.” United

States v. Frye, 402 F.3d 1123, 1128 (11th Cir. 2005) (quotation omit-

ted). There need not be “uncontroverted evidence of guilt.” United

States v. Owen, 858 F.2d 1514, 1516–17 (11th Cir. 1988).

Generally, an error that affects substantial rights is one that

is “prejudicial,” in that it “affected the outcome of the district court

proceedings.” United States v. Olano, 507 U.S. 725, 734 (1993). A

defendant who seeks to reverse “his conviction after a guilty plea,

on the ground that the district court committed plain error under

Rule 11 must show a reasonable probability that, but for the error,

he would not have entered the plea.” United States v. Dominguez

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4 Opinion of the Court 23-13871

Benitez, 542 U.S. 74, 83 (2004). “A variance from the requirements

of [Rule 11] is harmless error if it does not affect substantial rights.”

Id. at 80 (quoting Fed. R. Crim. P. 11(h)).

To establish that a defendant has committed a RICO viola-

tion under 18 U.S.C. § 1962(c), the government must prove:

“(1) the existence of an enterprise; (2) that the enterprise affected

interstate commerce; (3) that the defendants were employed by or

associated with the enterprise; (4) that the defendants participated,

either directly or indirectly, in the conduct of the affairs of the en-

terprise; and (5) that the defendants participated through a pattern

of racketeering activity.” United States v. Starrett, 55 F.3d 1525, 1541

(11th Cir. 1995) (footnote omitted). A “pattern of racketeering ac-

tivity” refers to at least two acts of racketeering activity within the

span of ten years. Id.

Wire fraud in violation of 18 U.S.C. § 1343 qualifies as a

“racketeering activity.” 18 U.S.C. § 1961(1)(B). To convict a de-

fendant for wire fraud, the government must prove that he (1) in-

tentionally participated in a scheme to defraud and (2) utilized in-

terstate mails or wires in furtherance of that scheme. United States

v. Maxwell, 579 F.3d 1282, 1299 (11th Cir. 2009). “A scheme to de-

fraud requires proof of a material misrepresentation, or the omis-

sion or concealment of a material fact calculated to deceive another

out of money or property.” Id. And “[a] misrepresentation is ma-

terial if it has a natural tendency to influence, or [is] capable of in-

fluencing, the decision maker to whom it is addressed.” Id. (quota-

tion marks omitted).

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Here, the statement of facts attached to Howard’s plea

agreement contains facts sufficient for the district court to “reason-

ably find that the defendant was guilty.” Frye, 402 F.3d at 1128. He

has admitted to the following: being the founder and president of

Howard & Associates and The Cambridge Entities; hiring as invest-

ment manager and then actively concealing the past of D.W.R., a

convicted felon barred by the SEC from engaging in investment

work; convincing former NFL players to invest over $4 million

with The Cambridge Entities; and misrepresenting the nature of

clients’ investments and returns. The district court, considering

these facts, found that the plea had a sufficient factual basis. We

hold that the district court did not commit plain error in accepting

the plea.

B

The Due Process Clause requires that a guilty plea be know-

ing and voluntary. McCarthy v. United States, 394 U.S. 459, 466

(1969). To determine whether the waiver is knowing and volun-

tary, a district court accepting a plea of guilty must comply with

the three “core objectives” of Rule 11 by ensuring that: (1) the

guilty plea is free from coercion; (2) the defendant understands the

nature of the charges; and (3) the defendant understands the con-

sequences of his plea. United States v. Presendieu, 880 F.3d 1228,

1238 (11th Cir. 2018). To comply with the first core principle, Rule

11(b)(2) requires the court to ensure that the plea did not result

from force, threats, or promises not included in the plea agree-

ment. Fed. R. Crim. P. 11(b)(2). Whether the court has complied

with the second core principle depends on a variety of factors,

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6 Opinion of the Court 23-13871

including the complexity of the offense and the defendant’s intelli-

gence and education. Presendieu, 880 F.3d at 1238. To comply with

the third core principle, the district court must inform the defend-

ant of the rights that he gives up by pleading guilty, the court’s au-

thority to impose certain punishments, and the possibility of a per-

jury prosecution for false statements during the plea colloquy.

United States v. Moriarty, 429 F.3d 1012, 1019 (11th Cir. 2005); see

also Fed. R. Crim. P. 11(b)(1). The district court must address the

defendant personally to ensure he understands the nature of the

charges and the potential consequences of a guilty plea. United

States v. Lewis, 115 F.3d 1531, 1535 (11th Cir. 1997); Fed. R. Crim.

P. 11(b)(1).

Howard’s plea was knowing and voluntary. He signed a

written plea agreement that explicitly detailed the conduct to

which he was admitting and the rights he was waiving. At How-

ard’s change-of-plea hearing, the court addressed him personally to

ensure that he understood his rights, the rights he would be waiv-

ing by pleading guilty, and the nature of the charge. Howard there-

upon affirmed his understanding and confirmed that he had “just

signed” the plea bargain “[i]n the courtroom” after having “seen a

copy of it.” He moreover affirmatively stated multiple times that

he was guilty of the conduct outlined in the statement of facts. The

most he could say for himself was that he did not intend for the

victims “not to have money at the end of their investment.” How-

ever, that is irrelevant here given his concession that “I did not in-

form them, and I had a duty to do that and I didn’t do that.” After

clarifying one last time that Howard wanted to plead guilty, the

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23-13871 Opinion of the Court 7

district court judge finally noted that Howard understood the con-

sequences and was “well-presented by counsel here” before accept-

ing his guilty plea. We find no constitutional defect here.

II

A

We review the procedural reasonableness of a sentence for

abuse of discretion. United States v. Barrington, 648 F.3d 1178, 1194

(11th Cir. 2011). The district court abuses its discretion if it applies

an incorrect legal standard, follows improper procedures in deter-

mining the sentence, or makes clearly erroneous factual findings.

Id. We review a district court’s interpretation of the Sentencing

Guidelines de novo, and its determination of the loss amount for

clear error. Maxwell, 579 F.3d at 1305.

However, when a party fails to make specific objections at

sentencing after being given an opportunity to do so by the district

court, challenges to the sentence on appeal will be reviewed only

for plain error. United States v. Ramirez-Flores, 743 F.3d 816, 821

(11th Cir. 2014). To preserve an objection, a defendant “must raise

that point in such clear and simple language that the trial court may

not misunderstand it.” Id. (quotation marks omitted). Addition-

ally, if a defendant fails to adequately brief an issue on appeal, it is

considered abandoned. United States v. Cunningham, 161 F.3d 1343,

1344 (11th Cir. 1998). This includes mere “passing reference[s]”

made in the initial brief. United States v. Brown, 125 F.4th 1043, 1054

(11th Cir. 2025).

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8 Opinion of the Court 23-13871

A district court must consult the Sentencing Guidelines and

take them into account when determining a defendant’s sentence.

United States v. Booker, 543 U.S. 220, 264 (2005). The Sentencing

Guidelines allow the consideration of relevant conduct to deter-

mine the guideline range. U.S.S.G. § 1B1.3(b). Under the 2024 and

2025 Guidelines, “[r]elevant conduct does not include conduct for

which the defendant was criminally charged and acquitted in fed-

eral court, unless such conduct also establishes, in whole or in part,

the instant offense of conviction.” Id. § 1B1.3(c).

When calculating the guideline range, a district court may

rely on factual findings based on facts admitted during a defend-

ant’s guilty plea, undisputed statements in the presentence investi-

gation report (“PSI”), or evidence presented during the sentencing

hearing. United States v. Matthews, 3 F.4th 1286, 1289 (11th Cir.

2021). Undisputed statements in a defendant’s PSI are deemed ad-

mitted. Fed. R. Crim. P. 32(i)(3)(A); United States v. Beckles, 565 F.3d

832, 844 (11th Cir. 2009). If a defendant challenges one of the fac-

tual bases of his sentence, the government has the burden of prov-

ing the disputed fact by a preponderance of the evidence. United

States v. Aguilar-Ibarra, 740 F.3d 587, 592 (11th Cir. 2014).

The government also has the burden of proving loss

amounts attributed to the defendant by a preponderance of the ev-

idence. United States v. Cavallo, 790 F.3d 1202, 1232 (11th Cir. 2015).

And “a sentencing court need only make a reasonable estimate of

the loss, given the available information.” Id. (quotation omitted).

“The court, however, cannot merely speculate as to the proper

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23-13871 Opinion of the Court 9

amount of loss, and, if the amount suggested by the government is

contested, the government must support its estimate with reliable

and specific evidence.” United States v. Yeager, 331 F.3d 1216, 1224

(11th Cir. 2003) (citation modified). Additionally, all relevant con-

duct may be considered in determining the loss amount if the gov-

ernment can prove the conduct by a preponderance of the evi-

dence. United States v. Hamaker, 455 F.3d 1316, 1336 (11th Cir.

2006); see also Cavallo, 790 F.3d at 1233-34. And the district court

may hold all participants in a conspiracy responsible for the losses

resulting from the reasonably foreseeable acts of co-conspirators in

furtherance of the conspiracy. United States v. Hunter, 323 F.3d

1314, 1319 (11th Cir. 2003). A district court should deduct any

losses returned to the victims when calculating the total loss

amount for sentencing purposes, but any error in failing to do so is

harmless where the deduction would not alter the threshold

amount level for triggering the upward adjustment. See, e.g., United

States v. Woodard, 459 F.3d 1078, 1087 (11th Cir. 2006).

First, Howard contends that it was erroneous for the district

court, relying on the presentence report, to consider as “relevant

conduct” actions beyond those conceded in his guilty plea. He ar-

gues this violates his rights under both the Fifth and Sixth Amend-

ments, as well as U.S.S.G. § 1B1.3(b). As he did not object to the

consideration of this “relevant conduct” at sentencing, we review

for plain error.

The district court did not err. As for the constitutional

claims, we have repeatedly rejected this sort of argument in the

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past. See, e.g., United States v. Chau, 426 F.3d 1318, 1323 (11th Cir.

2005) (“As we have explained, all nine justices [in Booker] agreed

that the use of extra-verdict enhancements in an advisory guide-

lines system is not unconstitutional.” (citation modified)). As for

the guidelines claim, even assuming the 2024 amendment to the

Guidelines applies to this case, § 1B1.3(c) only bars “conduct for

which the defendant was criminally charged and acquitted in federal

court.” U.S.S.G. § 1B1.3(c) (emphasis added). There was no ac-

quittal here, and therefore no error.

Second, Howard contends that the district court errone-

ously calculated the loss amount. The district court found that

Howard was responsible for approximately $12.6 million in actual

loss. Howard doesn’t dispute this figure as a starting point for the

calculations, but rather contends that the district court should have

credited other things (e.g., loans made, value of other fund invest-

ments, the value of litigation claims) against this loss to reduce it.

Since Howard objected below, we review for clear error. See Max-

well, 579 F.3d at 1305.

The district court did not clearly err in calculating the loss

amount. Commentary to the Sentencing Guidelines delineates sit-

uations in which credits must be applied against losses. This in-

cludes the “money returned, and the fair market value of the prop-

erty returned and the services rendered,” before the offense was

detected. U.S.S.G. § 2B1.1 cmt. 3(D)(i). “In a case involving a

fraudulent investment scheme . . . loss shall not be reduced by the

money or the value of the property transferred to any individual

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investor in the scheme in excess of that investor’s principal invest-

ment.” Id. § 2B1.1 cmt. 3(E)(iv).

The losses here can be broken down into four categories: (1)

Losses to investors (former NFL players) associated with The Cam-

bridge Entities; (2) Losses to Preferred Capital (a third-party

lender); (3) Losses to Virage Capital (a litigation lender); and (4)

Losses to a retired university professor (a real estate investor).

Howard contends that he’s entitled to credits in the first

three categories. He first claims the district court should have

granted him credits in the first category for money paid out to vic-

tims including loan balances, medical and travel costs, and the

value of the fund’s investment in a startup. However, loans

granted are not the same thing as money given out—with loans

there’s an expectation of a return with interest. These loans are

also an entirely separate financial transaction from the funds fraud-

ulently raised from investors, and therefore cannot be credited

against one another. U.S.S.G. § 2B1.1 cmt. (3)(E)(iv). As for the

medical and travel costs, money spent in a fraudulent scheme

doesn’t become legitimate simply because legitimate businesses in-

cur these expenses. United States v. Campbell, 765 F.3d 1291, 1305

(11th Cir. 2014). As these costs helped “perpetuat[e] the scheme,”

they should not be credited against the loss amount. Id. at 1306.

Further, the district court did not act unreasonably in determining

the value of equity interest in the startup as $0 in light of unsub-

stantiated sales projections and the absence of any marketable

product.

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12 Opinion of the Court 23-13871

As for the second category, Howard claims that losses to

Preferred Capital should be offset by the value of the outstanding

principal of the loans, at least for the players who had already re-

ceived settlements from the NFL. However, the district court did

not act unreasonably in valuing these loans at $0. These were high-

risk loans and the practical chance of getting anything off these

loans, informed by the testimony of Preferred Capital’s General

Counsel and lead underwriter, was close to zero.

Howard contends that the third category of losses should be

offset by the collateral of these loans: the value of the attorneys’

fees owed to Howard from the NFL and tobacco settlements. The

district court, however, did not clearly err in valuing this collateral

at $0. There are a number of practical and legal difficulties with

recovering the fees, implicating questions of Howard’s disbarment

and general misdeeds, as well as plaintiffs changing counsel in the

tobacco litigation. It is therefore reasonable to value this collateral

at $0.

Howard also argues more generally that he was not the

proximate cause of the losses suffered by those within these same

three categories. He points to the “complex medical/legal process

that derailed [the] NFL claims” as an intervening event. However,

we find the district court did not err. Howard’s ability to raise

money in the first place stemmed from misrepresentations he

made about his own operations and the underlying NFL claims.

The fact that the some NFL settlement claims came later than ex-

pected, and some not at all, doesn’t break this causal chain.

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Complex medical and legal processes are reasonably foreseeable

parts of pursuing settlement. See United States v. Stein, 846 F.3d

1135, 1154–55 (11th Cir. 2017).

B

We also apply “the familiar abuse-of-discretion standard”

when reviewing the substantive reasonableness of a sentence. Gall

v. United States, 552 U.S. 38, 46 (2007). This standard is a deferential

one, and “it is only the rare sentence that will be substantively un-

reasonable.” United States v. McQueen, 727 F.3d 1144, 1156 (11th

Cir. 2013). “The party challenging the sentence bears the burden

of establishing that the sentence is unreasonable in light of both the

record and the 3553(a) factors.” United States v. Witt, 43 F.4th 1188,

1198 (11th Cir. 2022).

For a sentence to be substantively reasonable, the district

court must impose a “sentence sufficient, but not greater than nec-

essary, to comply with the purposes set forth” in § 3553(a)(2),

which are the need for the sentence to reflect the seriousness of the

offense, promote respect for law, provide just punishment, afford

adequate deterrence, protect the public, and provide the defendant

with needed correctional treatment. 18 U.S.C. § 3553(a)(2). The

district court must also consider: (1) the nature and circumstances

of the offense and the history and characteristics of the defendant;

(2) the types of sentences that are available; (3) the appropriate

types of sentences and sentencing range established by the sentenc-

ing guidelines; (4) policy statements by the Sentencing Commis-

sion; (5) the need to avoid sentencing disparities between similarly

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14 Opinion of the Court 23-13871

situated defendants; and (6) the need to provide restitution. Id.

§ 3553(a)(1), (3)-(7).

We consider “the totality of the circumstances” when deter-

mining the substantive reasonableness of a sentence. United States

v. Pugh, 515 F.3d 1179, 1191 (11th Cir. 2008) (quoting Gall, 552 U.S.

at 51). We also “appreciate the institutional advantage that district

courts have in applying and weighing the Section 3553(a) factors in

individual cases,” but “the district court’s choice of sentence is not

unfettered.” Id. at 1190–91. Although district courts are required

to consider all the factors enumerated in § 3553(a), they need not

weigh all factors equally. United States v. Grushko, 50 F.4th 1, 19

(11th Cir. 2022). A court “may give greater weight to some factors

over others or even attach great weight to a single factor—a deci-

sion that is within its sound discretion.” Id. Further, a “district

court does not need to discuss or state each factor explicitly.”

United States v. Gonzalez, 550 F.3d 1319, 1324 (11th Cir. 2008). We

do not take a court’s failure to discuss certain mitigating evidence

to mean “that the court erroneously ignored or failed to consider

this evidence in determining” a sentence. United States v. Amedeo,

487 F.3d 823, 833 (11th Cir. 2007) (quotation marks omitted).

There are a range of reasonable sentences for a given of-

fense. See United States v. Irey, 612 F.3d 1160, 1190 (11th Cir. 2010)

(en banc). We will vacate a sentence “if, but only if, we ‘are left

with the definite and firm conviction that the district court com-

mitted a clear error of judgment in weighing the § 3553(a) factors

by arriving at a sentence that lies outside the range of reasonable

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sentences dictated by the facts of the case.’” Id. (quoting Pugh, 515

F.3d at 1191). We may find that a district court has abused its dis-

cretion when it “unjustifiably relies on any single § 3553(a) factor,

fails to consider pertinent § 3553(a) factors, bases the sentence on

impermissible factors, or selects the sentence arbitrarily.” Grushko,

50 F.4th at 19. But “[a] sentence that suffers from one of these

symptoms is not per se unreasonable.” Id. Instead, it is subject to

review based on “the totality of the circumstances to determine the

sentence’s reasonableness.” Id.

“We ordinarily expect a sentence within the guidelines

range to be reasonable.” United States v. Dorsey, 554 F.3d 958, 962

(11th Cir. 2009). Further, “[a] sentence well below the statutory

maximum indicates reasonableness.” United States v. Thomas, 108

F.4th 1351, 1357 (11th Cir. 2024).

We find Howard’s sentence to be substantively reasonable.

He argues that he should have received a below-guideline sentence

because of mitigating factors like his age, lack of criminal history,

and intent to repay all victims. However, the district court did not

abuse its discretion in concluding that the seriousness of the fraud,

the need for just punishment, and the need for general and specific

deterrence outweighed these mitigation factors. Additionally, the

sentence of 168 months is well below the statutory maximum of

210 months, indicating reasonableness.

III

We review the legality of a restitution order de novo, while

we review the sentencing court’s determination of restitution

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16 Opinion of the Court 23-13871

value for abuse of discretion. United States v. Robertson, 493 F.3d

1322, 1330 (11th Cir. 2007). The factual findings underlying the

restitution order are reviewed for clear error. Id.

Two principles underpin the awarding of restitution: (1) the

purpose of restitution is to make victims whole to the greatest ex-

tent possible, rather than to punish the defendant; and (2) the cal-

culation of restitution is not an exact science. United States v. Mar-

tin, 803 F.3d 581, 594–95 (11th Cir. 2015). The government may

thus “provide a reasonable estimate” of the amount owed. Id. at

595. A restitution award “must be based on the amount of loss

actually caused by the defendant’s conduct.” United States v. Foster,

878 F.3d 1297, 1307 (11th Cir. 2018) (quotation omitted).

The method for calculating actual loss, when calculating the

loss amount applicable to a defendant under the Guidelines, is

“largely the same as the method for establishing actual loss to iden-

tifiable victims.” Stein, 846 F.3d at 1153 (quotation marks omitted).

Consequently, “[i]n most cases, the amount of actual loss under the

guidelines will be the same as the restitution figure.” Id.

Here, the district court did not clearly err in its calculation

of the restitution value. The government proved by a preponder-

ance of the evidence that the actual loss amount resulting from

Howard’s conduct was $12,641,941.06—the amount of the actual

loss. The same rationale for denying credits against that loss there

applies with equal force here.

IV

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When reviewing a forfeiture judgment, we review a district

court’s findings of fact for clear error and its conclusions of law de

novo. United States v. Esformes, 60 F.4th 621, 631–32 (11th Cir.

2023).

Forfeiture is part of the criminal penalty against a defendant

convicted of RICO charges under 18 U.S.C. § 1962. 18 U.S.C.

§ 1963(a)(3). Section 1963 provides that an individual convicted of

such charges must “forfeit to the United States . . . any property

constituting, or derived from, any proceeds which the person ob-

tained, directly or indirectly, from racketeering activity.” Id. The

government bears the burden of proving by a preponderance of the

evidence the elements of criminal forfeiture. United States v. Dicter,

198 F.3d 1284, 1289 (11th Cir. 1999).

Here, the district court committed no error in entering a for-

feiture money judgment of $10,651,941.40. Howard was in fact

convicted of RICO charges under 18 U.S.C. § 1962. The district

court’s estimate of property derived from racketeering is also rea-

sonable. The government presented the testimony of IRS investi-

gator Justin Wisnakas below, who, by tracing Howard’s financial

transactions, arrived at this $10.6 million figure. The district court

did not clearly err in crediting this testimony.

V

In sum, we hold that that the district court did not err in ac-

cepting Howard’s guilty plea and determining that it was made

knowingly and voluntarily. It also did not commit any procedural

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18 Opinion of the Court 23-13871

or substantive errors at sentencing. Finally, its calculation of and

imposition of restitution and forfeiture were reasonable.

AFFIRMED.