Michael Riolo v. United States

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[PUBLISH]

In the

United States Court of Appeals

For the Eleventh Circuit

____________________

No. 20-12206

____________________

MICHAEL RIOLO,

Petitioner-Appellant,

versus

UNITED STATES OF AMERICA,

Respondent-Appellee.

____________________

Appeal from the United States District Court

for the Southern District of Florida

D.C. Docket Nos. 9:11-cv-81028-KAM,

9:09-cr-80058-KAM-1

____________________

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2 Opinion of the Court 20-12206

Before JORDAN, JILL PRYOR, and MARCUS, Circuit Judges.

JILL PRYOR, Circuit Judge:

Michael Riolo appeals the district court’s denial of his 28

U.S.C. § 2255 motion to vacate his 293-month prison sentence and

convictions.1 Riolo argued to the district court that his trial coun-

sel, Theresa Van Vliet, provided ineffective assistance of counsel.

Specifically, Riolo asserted that Van Vliet told him if he pled guilty

to five counts of mail fraud, he would serve no more than 10 years

in prison because she had a deal with the government that his sen-

tencing range would be 97–121 months’ imprisonment under the

Sentencing Guidelines. Based on Van Vliet’s representations, Riolo

maintained, he pled guilty when he otherwise would have pro-

ceeded to trial.

The district court held an evidentiary hearing on Riolo’s

§ 2255 motion. After reviewing the evidence, the district court

found that Van Vliet never represented to Riolo that she had a deal

with the government about his guideline range. More than that,

the district court found that before the change-of-plea hearing, Van

Vliet thoroughly apprised Riolo of the federal sentencing process,

explaining that the United States Probation Office would make a

recommendation to the district court about his guideline range and

1 Riolo’s 293-month sentence is an amalgam of five sentences, all for mail

fraud convictions pursuant to 18 U.S.C. § 1341. For clarity, we refer to the five

sentences as a single “sentence” like the parties do.

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20-12206 Opinion of the Court 3

that the district court would ultimately determine his guideline

range for itself. Based on its factual findings, the district court de-

nied Riolo’s § 2255 motion.

On appeal, Riolo urges us to take another look at the evi-

dence. If we do, he argues, we will find that several of the district

court’s factual findings are clearly erroneous. In the light of his ver-

sion of the facts—that Van Vliet assured him she had a deal with

the government about his guideline range—Riolo urges us to con-

clude that she provided ineffective assistance of counsel. Even leav-

ing aside the disputed facts, he adds, Van Vliet underestimated his

guideline range by more than 100 months. That alone, he argues,

constitutes ineffective assistance.

After careful review, and with the benefit of oral argument,

we find no clear error in the district court’s factual findings. We

therefore conclude that Van Vliet did not provide Riolo with inef-

fective assistance by telling him she had an agreement with the

government about his guideline range. We also conclude that Van

Vliet did not provide ineffective assistance by underestimating Ri-

olo’s guideline range. The district court’s judgment is affirmed.

I. BACKGROUND

We begin by summarizing Riolo’s offense conduct, Van

Vliet’s representation of him, the change-of-plea hearing, the sen-

tencing hearing, and Riolo’s direct appeal. Next, we review the

events that followed Riolo’s § 2255 motion, including two previous

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4 Opinion of the Court 20-12206

denials, appeals, and remands of his case, as well as the district

court’s final order and judgment on appeal.

A. Offense Conduct

From August 1999 to December 2008, Riolo convinced

more than 80 people to invest money in two corporations for

which he was the sole officer and employee: Sterling Wentworth

Currency Group, Inc. (“Sterling”) and LaSalle International Clear-

ing Corporation (“LaSalle”). Riolo told investors that he would in-

vest their money in foreign currency trading. Investors sent per-

sonal checks or wire transfers to the Sterling and LaSalle bank ac-

counts.

But Riolo did not invest the funds he received. With signa-

tory authority over the Sterling and LaSalle bank accounts, he with-

drew investors’ funds and used their money for other purposes. He

spent at least some of the money to pay for a home, multiple auto-

mobiles, a boat, jet skis, and other luxury items. If an investor

wanted to withdraw funds, Riolo would send the money he re-

ceived from other investors to cover the disbursement. Using this

technique, he disbursed over $29.5 million to withdrawing inves-

tors, claiming they were receiving their principal investment and

returns when most, if not all, of the payments were made with

other investors’ funds. To perpetuate this Ponzi scheme, Riolo pre-

pared sophisticated profit and loss statements for the investors—

statements which falsely reflected that their money had been in-

vested and was earning substantial returns. Over the nearly 10-year

period, Riolo collected more than $44 million from investors.

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B. Van Vliet’s Representation of Riolo

In January 2009, the Federal Bureau of Investigation (“FBI”)

served Riolo at his house with a subpoena for corporate records of

Sterling and LaSalle. While the FBI was on his property, Riolo con-

tacted his civil lawyer, Bart Houston. Houston, in turn, reached out

to his law partner, Theresa Van Vliet, a highly experienced criminal

attorney who had been in private practice for 18 or 19 years and

was a former Assistant United States Attorney. Houston put Van

Vliet on the phone with Riolo, who then put Van Vliet on the

phone with the FBI. Van Vliet explained to the FBI agent that her

law firm had the records responsive to the subpoena.

Riolo met Van Vliet in person shortly after the FBI’s visit to

his house. He told her that he had been running Sterling and

LaSalle for approximately 10 years and that he had not made any

trades in foreign currency during that time. He explained that he

had taken in approximately $44 million from investors. He admit-

ted that he had mailed investors fraudulent statements reflecting

that their money had been invested when it had not been. Van

Vliet advised that he could face several counts of mail and wire

fraud.

Van Vliet continued to communicate regularly with Riolo

over the following months. She received a proposed bill of infor-

mation from the government and engaged in plea negotiations on

his behalf. She told him that, given the overwhelming evidence

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6 Opinion of the Court 20-12206

against him, she could not mount a successful defense of his case.

Riolo told her that the most important consideration for him was

the length of any prison sentence he might receive. She explained

that his sentence would depend in part on his guideline range un-

der the Sentencing Guidelines. If he pled guilty, she advised, he

would likely have the benefit of a three-point reduction under the

“acceptance of responsibility” guideline. Civ. Doc. 74-5 at 3 ¶ 5 (in-

ternal quotation marks omitted). 2 She told him that a further re-

duction could be possible if he cooperated with the authorities. If

he wanted the lowest sentence possible, she advised, his best

course of action was to plead guilty and offer his cooperation to the

government. In May 2009, the government formally charged Riolo

by information with five counts of mail fraud.

1. Van Vliet’s May 7, 2009 Meeting with Riolo

On May 7, 2009, Van Vliet met with Riolo to provide an es-

timate of his guideline range. Houston and Riolo’s then-wife, Lori

Ann Gary, also attended the meeting. Van Vliet told Riolo that

based on her calculations, aided by the work of an associate at her

law firm, the district court likely would find an offense level of 30,

a criminal history category of I, and a resulting guideline range of

97–121 months’ imprisonment. She flagged for him, however, that

a higher guideline range was possible if the district court imposed

2 “Civ. Doc.” refers to docket entries in the district court in case number 9:11-

cv-81028-KAM. “Crim. Doc.” refers to docket entries in the district court in

case number 9:09-cr-80058-KAM-1.

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a four-point enhancement for violating commodities laws while

being a commodities trading advisor. But it was Van Vliet’s opinion

that the commodities law enhancement would not apply. She reas-

sured Riolo by telling him that the government had independently

reached the same guideline-range calculation—that he would have

an offense level of 30 and a criminal history category of I, with a

resulting guideline range of 97–121 months’ imprisonment.

The parties offered conflicting evidence regarding the May

7, 2009 meeting at the evidentiary hearing in Riolo’s § 2255 pro-

ceedings. Riolo, Gary, and Houston all testified that Van Vliet told

those in attendance she had reached a binding “deal” or “agree-

ment” with the government that Riolo’s offense level would be 30,

with a resulting guideline range of 97–121 months’ imprisonment.

Gary testified that she specifically asked Van Vliet whether he

could possibly “get more than 10 years” if he pled guilty. Civ. Doc.

83 at 8. Van Vliet reassured her by saying “no, . . . this was the plea

agreement that had been agreed upon with the prosecution and

her.” Id. at 7. Houston, a civil lawyer unfamiliar with criminal sen-

tencing, came away with the impression that Van Vliet and the

government had something akin to “a stipulation in [civil] practice”

about Riolo’s guideline range. Id. at 64. And according to Riolo,

Van Vliet suggested that a guideline range of 97 to 121 months’

imprisonment “was locked in.” Id. at 108.

Van Vliet testified adamantly to the contrary. She said that

“[n]ever . . . in [her] life” had she communicated to a client that she

could reach a deal with the government about a defendant’s

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8 Opinion of the Court 20-12206

guideline range. Id. at 237. She broadly denied ever telling Riolo

that there was any sort of deal or agreement between her and the

government about his sentence. She testified that she told Riolo,

on multiple occasions, about “all of the nuances of the sentencing

guidelines and his possible exposure.” Civ. Doc. 74-5 at 6 ¶ 18. For

one thing, she told him that the probation office would make an

independent guideline calculation to aid the sentencing court. For

another, she informed him that the sentencing court would not be

bound by either of the parties’ estimates regarding his guideline

range or ultimate sentence.

2. Van Vliet’s May 11, 2009 Meeting with Riolo

Riolo and Van Vliet met again a few days later, on May 11,

2009. This time they met for lunch at a restaurant. Also attending

the meeting was Michael McManus, a former DEA agent turned

private investigator who worked with Van Vliet. Van Vliet hired

McManus to aid in Riolo’s representation. His role was to help Ri-

olo understand “how he could cooperate” with law enforcement

to obtain a potential guideline reduction. Civ. Doc. 83 at 188.

At the evidentiary hearing in Riolo’s § 2255 action, the par-

ties offered conflicting testimony about the lunch meeting. Accord-

ing to McManus’s testimony, Van Vliet took the opportunity at the

meeting to reexplain to Riolo how federal sentencing worked.

McManus testified that Van Vliet told Riolo that the probation of-

fice would prepare a presentence investigation report (“PSR”), and

the district judge would ultimately determine his guideline range

and could “depart upwards” or “downwards.” Id. at 192. McManus

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“kinda got the feeling that this may have been discussed be-

fore, . . . because she was saying, now, understand again, or some-

thing to that effect . . . you’ve got to have a presentence report.” Id.

Van Vliet also remembered telling Riolo at this lunch meeting

about “the Sentencing Guidelines . . . , how a plea works, how the

Court goes into it, how, after he does a plea there would be a PSR.”

Civ. Doc. 84 at 41. In contrast, Riolo denied that Van Vliet was pre-

sent at his May 11, 2009 lunch with McManus and denied that she

went over this information with him.

3. Van Vliet’s Review of the Plea Agreement and Fac-

tual Proffer with Riolo

Less than a week after the lunch meeting with McManus,

Van Vliet received a copy of the plea agreement from the govern-

ment and sent it to Riolo by email. In the email Van Vliet said she

“talked to [the prosecutor] and his calculations match ours. That is

a level 30 with a range of 97 to 121 months. So any break we can

possibly get on cooperation will be critical.” Civ. Doc. 76-2 at 2.

The attached plea agreement—which Riolo admitted he re-

viewed—contained a thorough exposition of the federal sentencing

process, describing the Sentencing Guidelines, the probation of-

fice’s role in sentencing, and the fact that the court would not be

bound by the advisory guideline range.

In addition to the plea agreement, Van Vliet also received a

factual proffer from the government, which contained the factual

basis for Riolo’s guilty plea. Upon reviewing the proffer with Van

Vliet, Riolo raised a concern about a statement that Sterling

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purportedly traded in “futures contracts.” Crim. Doc. 14 at 6 ¶ 2.

Van Vliet raised his concern to the government, but it refused to

remove the futures contract language. She advised Riolo that the

language would not affect his guideline range. He signed the fac-

tual proffer.

C. Change-of-Plea Hearing, Sentencing, and Direct Appeal

In July 2009, the district court held a change-of-plea hearing.

At the hearing, after putting Riolo under oath, the district court

asked Riolo whether he had reviewed the plea agreement “fully

and completely” with Van Vliet and whether he understood it.

Crim. Doc. 16 at 6. He answered yes to both questions. The court

then asked whether Riolo had reviewed the factual proffer “fully

and completely” with Van Vliet and whether he understood it. Id.

at 18. Again, Riolo answered yes to both questions.

The district court also established that Riolo understood

how the sentencing process would work following his guilty plea.

The court sought to confirm his understanding that the probation

office would prepare a PSR to help the court determine his guide-

line range. Riolo confirmed that he understood. Then, after detail-

ing the procedure for filing objections to the PSR, the court asked

whether he knew that the district court—and no one else—would

determine his guideline range and sentence. Riolo answered

“[y]es.” Id. at 11. Lastly—with three separate questions—the dis-

trict court asked Riolo whether anyone had made “any promises or

representations” to him about his sentence. Id. at 12–13. Three

times, Riolo swore that no one had made any promises or

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representations to him about his sentence. After this thorough col-

loquy, the district court found him competent to enter an informed

plea and accepted his plea of guilty.

1. The Presentence Investigation Report

Following the change-of-plea hearing, the probation office

prepared the PSR. The PSR calculated Riolo’s offense level as 38,

not 30 as he and Van Vliet had discussed, and his criminal history

category as I, which yielded a guideline range of 235–293 months’

imprisonment.

The PSR included two four-point sentence enhancements

that Van Vliet had not included in her estimate. In calculating Ri-

olo’s guideline range, first, the PSR applied the four-point enhance-

ment for violation of a commodities law by a commodities trading

advisor—an enhancement that Van Vliet and Riolo had discussed,

but she had not included in her estimate. See U.S. Sent’g Guidelines

Manual § 2B1.1(16)(B) (U.S. Sent’g Comm’n 2008). Second, the

PSR applied another four-point enhancement for jeopardizing the

safety and soundness of a financial institution. See id.

§ 2B1.1(b)(14)(B). Neither Van Vliet nor the government had antic-

ipated the second enhancement. Van Vliet filed written objections

to both enhancements.

2. Riolo’s Reaction to the PSR Calculation

Riolo was “shocked” when he read the PSR. Civ. Doc. 83 at

124. He interpreted the PSR’s calculation to mean that “the AUSA

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had gone back on [his] deal” to assign Riolo an offense level of 30,

with a guideline range of 97 to 121 months’ imprisonment.

The day before his sentencing, Riolo drafted a letter to the

district court. In the letter, he sought to withdraw his plea or, in the

alternative, to obtain a continuance of his sentencing hearing, writ-

ing that he thought there was a “verbal agreement” between the

government and Van Vliet that he “would be released [from

prison] around the time [his] oldest child would enter high school.”

Civ. Doc. 76-5 at 3–4. He sent the draft letter to Houston, his civil

lawyer. Houston told Van Vliet about Riolo’s draft letter, and she

responded to Riolo in an email.

Van Vliet’s email encouraged Riolo not to attempt to with-

draw his guilty plea. She urged that withdrawal of his plea would

prove “a very, very difficult hurdle” and that it may have adverse

consequences, including the removal of any reduction he might re-

ceive for acceptance of responsibility or for cooperating with the

government. Civ. Doc. 74-4 at 1. But, she added, the decision to

send the letter was his alone. She encouraged him to seek a second

opinion on her advice.

Riolo called another lawyer, Richard Rosenbaum. Houston

had known Rosenbaum for years, and Riolo had earlier considered

hiring Rosenbaum to represent him instead of Van Vliet. During

their telephone conversation, Rosenbaum expressed reservations

about helping Riolo withdraw his plea with so little time left before

sentencing. Van Vliet was added to the conference call between

Riolo and Rosenbaum, and the three discussed Riolo’s case. Riolo

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left the phone call under the impression that Rosenbaum “was go-

ing to come and represent [him] at the [sentencing] hearing” the

next day. Civ. Doc. 83 at 128.

Later that evening, Rosenbaum called Van Vliet at her

home. She summarized for him the plea agreement, what occurred

at the change-of-plea hearing, and other information relevant to

Riolo’s case. Rosenbaum agreed with her opinion that Riolo should

not attempt to withdraw his plea. Rosenbaum was reluctant to tell

Riolo, however, because of Rosenbaum’s personal friendship with

Riolo and/or Houston. Van Vliet and Rosenbaum agreed to tell

Riolo that Rosenbaum could not represent him for another rea-

son—because Rosenbaum did not have enough time to process the

plea withdrawal before the sentencing the next morning. Rosen-

baum sent Van Vliet an email communicating that he could not

represent Riolo because he could not “clear conflict check and file

a Notice of Appearance” before sentencing and asking her to for-

ward the email to Riolo. Civ. Doc. 6 at 9.

3. Riolo’s 293-Month Sentence and Direct Appeal

The following morning, the district court held the sentenc-

ing hearing. There, Van Vliet reiterated her objections to the two

four-point enhancements. She conceded that the four-point com-

modities law enhancement could properly be applied to Riolo’s

sentence under the law, but she maintained her objection that the

enhancement should not apply because the prerequisites for the

enhancement existed only for a three-month period over the

course of the ten-year offense conduct. She also maintained her

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14 Opinion of the Court 20-12206

objection to the four-point enhancement for jeopardizing the

soundness of a financial institution. As to this enhancement, Van

Vliet argued that Sterling and LaSalle were not legitimate financial

institutions and so the enhancement for endangering the safety and

soundness of a financial institution should not apply. The district

court overruled the objections and adopted the findings in the PSR

as the findings of the court. After hearing live testimony from mul-

tiple victims, the district court imposed a sentence of 293 months’

imprisonment. 3

Riolo appealed, arguing in part that “the government prom-

ised him an offense level of 30,” rather than 38. United States v.

Riolo (Riolo I), 398 F. App’x 568, 570 (11th Cir. 2010) (unpublished).

The panel observed that “the record d[id] not contain any evidence

of such an agreement” and also noted that Riolo represented under

oath at the change-of-plea hearing “that no one had made any

promises or representations with respect to his sentence.” Id. The

panel affirmed. See id. at 571.

D. Riolo’s 28 U.S.C. § 2255 Motion and Previous Collateral Ap-

peals

3 Riolo’s sentence consisted of 240 months’ imprisonment on each of counts

one through four, all to run concurrently, and 53 months on count five, to run

consecutively to the sentence on the other counts, for a total of 293 months.

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Riolo next moved pro se to vacate his sentence pursuant to

28 U.S.C. § 2255. 4 His motion raised three distinct grounds for re-

lief on a theory of ineffective assistance of counsel. Under each

ground he listed several claims. The magistrate judge prepared a

report and recommendation, consolidating what appeared to be

duplicative and overlapping grounds and claims into three broad

theories for relief. After analyzing each one, the magistrate judge

recommended that Riolo’s § 2255 motion be denied. Following Ri-

olo’s objections, the district court adopted the magistrate judge’s

recommendation and entered a judgment. Riolo appealed.

On appeal, a panel of this Court construed Riolo’s pro se

motion as containing 13 ineffective assistance of counsel claims.

See Riolo v. United States (Riolo II), 567 F. App’x 684, 685–87 (11th

Cir. 2014) (unpublished). The panel ruled that the district court had

overlooked a few distinct ineffective assistance claims in denying

Riolo’s motion. See id. at 688. Citing Clisby v. Jones, 960 F.2d 925

(11th Cir. 1992) (en banc), the panel vacated the district court’s

judgment and remanded the case for the district court to consider

the unaddressed claims. Riolo II, 567 F. App’x at 688.

On remand, the district court referred the case back to the

magistrate judge for further review. The magistrate judge entered

another report and recommendation, this time addressing the

claims the district court had been directed to consider on remand.

4 Although Riolo initially proceeded pro se, he later retained counsel to repre-

sent him.

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16 Opinion of the Court 20-12206

The magistrate judge found no merit in the remaining claims and

again recommended that Riolo’s motion be denied. Riolo filed ob-

jections. The district court adopted the magistrate judge’s recom-

mendation over the objections and entered a final judgment. Riolo

appealed again.

On his second collateral appeal, Riolo argued that the district

court failed to hold an evidentiary hearing to which he was statu-

torily entitled. See Riolo v. United States (Riolo III), 783 F. App’x

917, 918 (11th Cir. 2019) (unpublished). The panel observed that

Riolo had made allegations that, if true, could amount to ineffec-

tive assistance of counsel. For example, Riolo alleged in his motion

that Van Vliet advised him “that the offense level had been prede-

termined” and that “there was no possibility” he would receive a

higher sentence than what was represented by her initial guideline

estimation. Id. at 919, 922 (internal quotation marks omitted). He

also alleged that Van Vliet “never informed him that the probation

office would conduct its own independent calculation of the of-

fense level for the court.” Id. at 922 (alteration adopted) (internal

quotation marks omitted). The panel vacated the judgment and re-

manded the case to the district court for an evidentiary hearing to

determine whether Riolo’s allegations were true. See id. at 923.

E. The District Court’s Order and Judgment

On remand the district court held a two-day evidentiary

hearing. Riolo testified at the hearing. He also presented testimony

from other witnesses, including Gary and Houston. The

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government’s witnesses included Van Vliet, McManus, and Sheila

Tierney, the probation officer who prepared Riolo’s PSR.5

After the hearing, the district court entered a written order

and judgment denying Riolo’s § 2255 motion. The court credited

Van Vliet’s testimony over the testimony from Riolo and his other

witnesses. It also considered the colloquy at the change-of-plea

hearing. Ultimately, the district court found that Van Vliet had

never represented to Riolo that she had a deal with the government

about his guideline range.

The district court made other findings of fact reflecting that

Van Vliet had thoroughly informed Riolo of the federal sentencing

process and the implications of his guilty plea. Specifically, the dis-

trict court found that—before the change-of-plea hearing—Van

Vliet reviewed each provision of the plea agreement with Riolo,

went over the factual proffer with him, explained the probation of-

fice’s role in sentencing, and discussed that the district court would

not be bound by any parties’ proposed calculation under the Sen-

tencing Guidelines. The court also found that Van Vliet did not

thwart Riolo’s attempt to withdraw his plea the day before sentenc-

ing when she communicated with Rosenbaum about his case. After

making these findings of fact, the district court determined that

Van Vliet did not provide ineffective assistance of counsel to Riolo.

The court denied Riolo’s § 2255 motion and granted a certificate of

5 Relevant testimony from the evidentiary hearing is summarized above in

Parts I.A–C.

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18 Opinion of the Court 20-12206

appealability on the question “of whether [his] guilty plea was

knowingly entered.” Doc. 91 at 29. 6

This is Riolo’s appeal.

II. LEGAL STANDARD

In § 2255 proceedings, we review legal conclusions de novo

and factual findings for clear error. See Martin v. United States,

949 F.3d 662, 667 (11th Cir. 2020). “A claim of ineffective assistance

of counsel is a mixed question of law and fact reviewed de novo.”

Id.

III. DISCUSSION

The question of whether an attorney provided ineffective

assistance of counsel in the context of a guilty plea is subject to the

familiar two-part inquiry first spelled out in Strickland v. Washing-

ton, 466 U.S. 668 (1984). The movant “must show (1) his counsel’s

performance was deficient and (2) the deficient performance prej-

udiced his defense.” Martin, 949 F.3d at 667 (citing Strickland, 466

U.S. at 687). Although the prejudice inquiry differs somewhat in

6 We note that the certificate of appealability is ambiguous in identifying the

question on appeal. On the one hand, the question could be understood as

asking whether the district court conducted a sufficient colloquy at the

change-of-plea hearing to render Riolo’s plea voluntary. On the other hand,

the question could be understood as asking whether Van Vliet provided inef-

fective assistance of counsel in preparing Riolo to plead guilty such that his

plea was not voluntary. The parties have consistently treated the district

court’s certificate of appealability as covering the latter question, and we do

the same.

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the guilty plea context, our review of the adequacy of an attorney’s

performance is much the same. To show deficient performance,

the movant must establish that his attorney’s representation “fell

below an objective standard of reasonableness.” Id. (internal quo-

tation marks omitted). The “petitioner bears the heavy burden of

showing that no competent counsel would have taken the action

that his counsel did take.” Gissendaner v. Seaboldt, 735 F.3d 1311,

1323 (11th Cir. 2013) (internal quotation marks omitted).

In this case, Riolo challenges the district court’s findings of

fact that underlaid the court’s conclusion that Van Vliet’s perfor-

mance in representing him was not deficient. Given our standard

of review, he can prevail in this appeal only if he can show that the

findings of fact were clearly erroneous. We therefore begin by re-

viewing the district court’s findings of fact for clear error. Seeing

no clear error in the district court’s findings, we next consider

whether Van Vliet provided ineffective assistance of counsel under

the facts found by the district court.

A. The District Court Committed No Clear Error in Making Its

Challenged Factual Findings.

Riolo contends that five of the district court’s factual findings

were clearly erroneous. Specifically, he asserts that the district

court clearly erred in finding that, before the change-of-plea hear-

ing, Van Vliet: (1) reviewed each provision of the plea agreement

with him; (2) reviewed the factual proffer with him days before the

hearing; (3) explained the probation office’s role in sentencing to

him; and (4) never communicated to him that there was a binding

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20 Opinion of the Court 20-12206

agreement with the government that his offense level would be 30

and that he would have a guideline range of 97–121 months’ im-

prisonment. Riolo further contends that the district court clearly

erred in finding that Van Vliet (5) did not thwart his attempt to

withdraw his guilty plea after the change-of-plea hearing.

A finding of fact is clearly erroneous only when we are “left

with a definite and firm conviction that a mistake has been com-

mitted.” United States v. Almedina, 686 F.3d 1312, 1315 (11th Cir.

2012) (internal quotation marks omitted). When there are two rea-

sonable constructions of the evidence, “the factfinder’s choice be-

tween them cannot be clearly erroneous.” Id. (internal quotation

marks omitted).

The district court made its findings of fact after crediting Van

Vliet’s testimony over Riolo’s and his other witnesses’ testimony.

“[W]e allot substantial deference to the factfinder . . . in reaching

credibility determinations with respect to witness testimony.” Riv-

ers v. United States, 777 F.3d 1306, 1316 (11th Cir. 2015) (alteration

adopted) (internal quotation marks omitted). “Generally, we refuse

to disturb a credibility determination unless it is so inconsistent or

improbable on its face that no reasonable factfinder could accept

it.” Id. at 1317 (internal quotation marks omitted). Keeping in mind

that we review the challenged findings of fact for clear error and

that we extend substantial deference to the district court’s credibil-

ity determinations, we proceed to the findings of fact in question.

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20-12206 Opinion of the Court 21

1. The District Court Did Not Clearly Err in Finding

that Van Vliet Reviewed the Plea Agreement with Ri-

olo Before the Change-of-Plea Hearing.

Riolo asserts that the district court clearly erred in finding

that Van Vliet reviewed each provision of the plea agreement with

him before the change-of-plea hearing. In support of his argument,

Riolo points to an inconsistency in Van Vliet’s testimony at the ev-

identiary hearing. She testified that she reviewed the plea agree-

ment with Riolo at the May 7, 2009 meeting—the meeting that

Gary and Houston also attended. As the government concedes, in

fact Van Vliet received the plea agreement on May 12, 2009, at the

earliest. Because she testified that she reviewed the plea agreement

with Riolo before she actually received the document, he argues,

the district court clearly erred in finding that she reviewed each

provision of the plea agreement with him before the change-of-plea

hearing.

Although Riolo is correct that a discrepancy exists, he at-

tempts to make a mountain out of this molehill. As an initial mat-

ter, the district court did not find that that Van Vliet reviewed the

plea agreement with Riolo on May 7, 2009. Instead, the court found

that she “went through each provision of the plea agreement” with

him at some point before the change-of-plea hearing. Civ. Doc. 91

at 23. Riolo offers no argument, nor any record citation, to under-

mine the finding that Van Vliet reviewed the plea agreement with

him before the change-of-plea hearing.

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22 Opinion of the Court 20-12206

Indeed, the record amply supports the district court’s find-

ing. In response to the court’s question at the change-of-plea hear-

ing regarding whether he had read the plea agreement and dis-

cussed it “fully and completely” with Van Vliet, Riolo answered,

under oath, “Yes, I did.” Crim. Doc. 16 at 6. “There is a strong pre-

sumption that the statements made during the [plea] colloquy are

true.” United States v. Medlock, 12 F.3d 185, 187 (11th Cir. 1994).

Riolo “bears a heavy burden” to show that his own statements,

made under oath at the time, were false. United States v. Rogers,

848 F.2d 166, 168 (11th Cir. 1988). At the evidentiary hearing, Riolo

attempted to explain away his testimony during the plea colloquy

by saying that he was “very emotional” and not as “focused as [he]

perhaps should have been on the questions being asked,” which led

him to make admissions that were not truthful. Civ. Doc. 83 at 119.

But the district court, having observed Riolo’s demeanor at the ev-

identiary hearing, did not find this explanation persuasive. Riolo

has not come close to carrying his heavy burden to show that his

own statements made during the plea colloquy were false. See Rog-

ers, 848 F.2d at 168.

Apart from Riolo’s own testimony at the change-of-plea

hearing, other evidence in the record supports the district court’s

finding that Van Vliet reviewed the plea agreement with Riolo. She

testified that she went through the “specific terms of [the] plea

agreement” with him before the change-of-plea hearing—testi-

mony that the district court credited over Riolo’s. Civ. Doc. 84 at

55. And her billing records indicate that she and Riolo spoke on

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20-12206 Opinion of the Court 23

May 19, 2009, which was before the change-of-plea hearing. Ac-

cording to her billing records for that day, she “follow[ed] up with

him regarding . . . [the] plea agreement.” Civ. Doc. 76-4 at 7. Riolo

fails to demonstrate that Van Vliet’s testimony was “so inconsistent

or improbable on its face that no reasonable factfinder could accept

it,” notwithstanding Van Vliet’s inability to remember precise

dates more than 10 years after the fact. Rivers, 777 F.3d at 1317 (in-

ternal quotation marks omitted). We conclude that there was no

clear error in the district court’s finding that Van Vliet reviewed

each provision of the plea agreement with Riolo at some point be-

fore the change-of-plea hearing.

2. The District Court Did Not Clearly Err in Finding

that Van Vliet Reviewed the Factual Proffer with Ri-

olo Before the Change-of-Plea Hearing.

Riolo next argues that the district court clearly erred in find-

ing that Van Vliet reviewed the factual proffer with him days be-

fore his change-of-plea hearing. The thrust of Riolo’s argument is

that he received the factual proffer on the morning of the change-

of-plea hearing and did not have time to digest and understand it

before the hearing took place.

He rests his argument that he received the factual proffer the

morning of the change-of-plea hearing on another chronological

inconsistency in Van Vliet’s testimony. Van Vliet initially took the

position that she sent the factual proffer, along with the plea agree-

ment, to Riolo on May 18, 2009, in an email. Riolo counters that

there was no factual proffer attached to her May 18, 2009 email. At

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24 Opinion of the Court 20-12206

the evidentiary hearing, however, Van Vliet acknowledged that

she had been mixed up on the dates, but she maintained that she

sent the factual proffer two or three days before the change-of-plea

hearing. The district court credited her live testimony.

The discrepancy, which Van Vliet explained to the district

court’s satisfaction, does not establish that the court’s finding was

clearly erroneous. Again, Riolo’s sworn testimony at the plea col-

loquy supports the district court’s finding. As with the plea agree-

ment, the district court asked whether Riolo had read the factual

proffer and discussed it “fully and completely” with Van Vliet.

Crim. Doc. 16 at 18. Riolo answered, “Yes, I did.” Id. At the eviden-

tiary hearing, he admitted to asking Van Vliet about language in

the factual proffer about futures contracts. She testified that she

raised Riolo’s concerns to the prosecutor and sought to have the

futures language removed, but the prosecutor refused. Riolo’s and

Van Vliet’s testimony at the evidentiary hearing that they discussed

the factual proffer together and had time to raise concerns to the

prosecutor, who in turn had time to deny their request, supports

the district court’s finding that Van Vliet reviewed the factual prof-

fer with Riolo days before the change-of-plea hearing. As if all this

were not enough, Riolo admitted on cross-examination that he

went over the factual proffer with Van Vliet and had enough time

to review it. There is no clear error in the district court’s finding of

fact.

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20-12206 Opinion of the Court 25

3. The District Court Did Not Clearly Err in Finding

that Van Vliet Reviewed the Probation Office’s Role

in Sentencing with Riolo Before the Change-of-Plea

Hearing.

Riolo next asserts that the district court clearly erred in find-

ing that Van Vliet reviewed the probation office’s role in sentenc-

ing ahead of the change-of-plea hearing. For this factual finding, Ri-

olo points to no chronological inconsistency in Van Vliet’s testi-

mony. Instead, he merely asserts that she was untruthful in testify-

ing that she told him about the probation office’s role in sentenc-

ing.

We are not persuaded. Once again, the plea colloquy sup-

ports the district court’s finding. During the colloquy, the district

court asked if Riolo understood that the probation office would

prepare a PSR and what the presentence investigation process

would entail. Riolo responded that he understood. Provided with

no reason to doubt this exchange at the plea colloquy, we again

find that Riolo’s sworn answers supported the district court’s find-

ing.

But that evidence was not all. Recall McManus testified that

he attended a lunch meeting with Van Vliet and Riolo on May 11,

2009, where Van Vliet communicated the probation office’s role to

Riolo. And Van Vliet also testified—credibly, according to the dis-

trict court—at the evidentiary hearing that “on more than one oc-

casion” she explained to Riolo that the probation office would

“make a guidelines calculation.” Civ. Doc. 83 at 238–39. All this

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26 Opinion of the Court 20-12206

evidence supports the district court’s finding that Van Vliet in-

formed Riolo of the probation office’s role in federal sentencing.

He has failed to demonstrate clear error in this finding of fact.7

4. The District Court Did Not Clearly Err in Finding

that Van Vliet Never Told Riolo that the Govern-

ment Had Agreed to an Offense Level of 30.

Riolo asserts that the district court erred in finding that Van

Vliet never told him that she had a deal with the government es-

tablishing that he would have an offense level of 30 and a guideline

range of 97–121 months’ imprisonment. 8 No clear error has been

7 In addition, it is undisputed that Riolo independently reviewed the plea

agreement before the change-of-plea hearing. The plea agreement also in-

formed Riolo of the probation office’s role in sentencing, noting that “the

Court w[ould] compute an advisory sentence under the Sentencing Guidelines

and . . . the applicable guidelines will be determined by the Court relying in

part on the results of a Pre-Sentence Investigation by the United States Proba-

tion Office . . . , which . . . will commence after the guilty plea has been en-

tered.” Civ. Doc. 74-5 at 21 ¶ 2.

8 Riolo argues in his brief:

The district court improperly avoided testimony and evidence

regarding the alleged offense level agreement, and then erred

by misinterpreting Riolo’s claims of an agreement on the of-

fense level instead as a sentence guarantee, and by judging Ri-

olo’s reasonable understanding of the agreement on defense

counsel’s post hoc alleged understanding rather than Riolo’s

understanding.

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20-12206 Opinion of the Court 27

shown. The plea colloquy again supports the district court’s find-

ing. The district court asked three times whether anyone had made

“any promises or representations” to Riolo about his sentence.

Crim. Doc. 16 at 12–13 (emphasis added). In response, Riolo swore

three times that he never received any promises or representations

about what his sentence might be. Riolo later testified at the evi-

dentiary hearing that he thought the sentencing judge was refer-

ring to “unseemly type[s] of things” in this line of questioning. Civ.

Doc. 83 at 122. We cannot say Riolo has carried his burden to show

that his own statements, made under oath at the time, were false.

Rogers, 848 F.2d at 168.

Other evidence in the record supports the district court’s

finding that Van Vliet never told Riolo she had a deal with the gov-

ernment about his offense level or guideline range. McManus tes-

tified that at the May 11, 2009 lunch meeting, Van Vliet informed

Riolo that “[i]t’s up to the judge to decide” his sentence and that

“[the judge] can depart upwards [or] downwards.” Civ. Doc. 83 at

192. And Van Vliet testified that she “never said that [the govern-

ment would] recommend 97 months or anything other than what

was in the plea agreement.” Id. at 232. All this evidence supports

the district court’s finding.

Appellant’s Br. at 17. In substance, we understand Riolo to be arguing that the

district court clearly erred in finding that Van Vliet never told him that there

was a binding agreement regarding his offense level and guideline range.

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28 Opinion of the Court 20-12206

Riolo points to the email Van Vliet sent to him on May 18,

2009, in which she wrote: “I have talked to [the prosecutor] and his

calculations match ours. That is a[n offense] level 30 with a range

of 97 to 121 months.” Civ. Doc. 76-2 at 2. This email, Riolo argues,

substantiates his assertion that Van Vliet had been telling him all

along that there was a binding agreement between her and the gov-

ernment as to his sentencing range. But the email is not the smok-

ing gun Riolo seems to think it is. The email says nothing about an

agreement between Van Vliet and the government. Rather, it indi-

cates that Van Vliet’s and the government’s independently-made

guideline estimates “match[ed].” Id. Van Vliet appears to have

sought to reassure herself and Riolo that her guideline calculation

was correct by comparing it with the government’s. The email

does not convince us that the district court clearly erred in finding

that she never told Riolo that she had a deal with the government

about his guideline range. We find no clear error here.

But even if we were to assume that Van Vliet did tell Riolo

that there was an agreement between herself and the government

with respect to his offense level or guideline range, the plea agree-

ment and portions of the plea colloquy sufficiently dispelled any

notion that such an agreement would be binding. The plea agree-

ment, for example, contained a detailed explanation about how the

court would determine his sentence. It explained that the proba-

tion office would prepare a PSR which would contain an estimate

of his guideline range. It also explained to Riolo that, although the

district court had to consider the advisory guideline range, it would

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20-12206 Opinion of the Court 29

not be bound by the range in sentencing him; the court could im-

pose an appropriate sentence above or below the guideline range.

At the change-of-plea hearing, the district court made sure

Riolo understood that Van Vliet could not have made any binding

agreement with the government about his guideline range or

about his sentence. It told Riolo that “even though [Van Vliet] may

have advised you based upon her understanding of the facts of the

case and her understanding of the law and the Sentencing Guide-

lines what she thinks or believes, in her best professional opinion,

the advisory guideline sentencing range will turn out to be, . . . my

decisions may be different from what she has advised you.” Crim.

Doc. 16 at 11. We are more than satisfied that Riolo was apprised

that the district court would not be bound by any guideline esti-

mate Van Vliet may have given him.

5. The District Court Did Not Clearly Err in Finding

that Van Vliet Never Prevented Riolo from With-

drawing His Guilty Plea.

Lastly, Riolo asserts that the district court clearly erred in

finding that Van Vliet never “thwarted” his attempt to withdraw

his guilty plea. Appellant’s Br. at 37. To support this argument, Ri-

olo points to the events that occurred the day before his sentenc-

ing. Riolo sent an email to Houston containing a draft letter ad-

dressed to the district court in which he requested a plea with-

drawal or, in the alternative, a continuance. Van Vliet got word of

Riolo’s letter and promptly wrote to advise him not to attempt to

withdraw his plea. She told him that the decision was his alone,

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30 Opinion of the Court 20-12206

however, and encouraged him to seek a second opinion. After he

received her email, Riolo contacted Rosenbaum, another attorney.

Van Vliet testified that later that evening Rosenbaum called her to

discuss the case in greater detail. During that conversation, Rosen-

baum reached the conclusion that “there was no viable basis for

withdrawal.” Civ. Doc. 74-5 at 5 ¶ 16. Rosenbaum then asked Van

Vliet to communicate to Riolo that he could not represent him at

sentencing. Taken together, Riolo contends that these circum-

stances establish that Van Vliet thwarted his attempt to withdraw

his guilty plea.

Riolo’s argument lacks merit. Van Vliet merely gave Riolo

advice on the possible consequences of attempting to withdraw his

guilty plea the day before sentencing. She did not stand in the way;

she reminded him that the decision was his alone. She also encour-

aged him to get a second opinion. When he took her advice and

sought a second opinion from Rosenbaum, she laid out the circum-

stances of his case for Rosenbaum, who independently concluded

that Riolo should not attempt to withdraw his guilty plea. Riolo

provides us with no basis to conclude that there is clear error in the

district court’s finding on this issue.

B. Van Vliet’s Representation of Riolo Was Not Deficient Un-

der Strickland.

Having reviewed all the factual findings Riolo challenges on

appeal, we now turn to whether the district court erred in conclud-

ing that Van Vliet did not provide constitutionally ineffective assis-

tance of counsel to Riolo. Our answer is no. First, we explain why

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20-12206 Opinion of the Court 31

our rejection of his argument that the district court’s factual find-

ings must be overturned renders Betancourt v. Willis, 814 F.2d

1546 (11th Cir. 1987)—the case upon which he principally relies—

inapposite. Second, we review his argument that Van Vliet’s mis-

calculation of his guideline range by itself amounts to ineffective

assistance of counsel.

1. Given the District Court’s Findings of Fact,

Betancourt Is Inapposite.

Riolo relied primarily on Betancourt in his brief and at oral

argument. In Betancourt, we affirmed the grant of a § 2254 petition

in which the petitioner, Jairo Betancourt, argued that his attorneys

provided ineffective assistance because of assurances they made

about his sentence before he pled guilty. Id. at 1547. Betancourt

argued that his attorneys told him that if he pled guilty, the state

court would initially impose a twelve-year sentence but “promised

to reduce his sentence later to equal the lowest sentence received

by either of his co-defendants in federal court.” Id. Betancourt pled

guilty based on his attorneys’ representations. Id. at 1548. He was

sentenced to twelve years’ imprisonment and three years’ proba-

tion. Id.

After one of Betancourt’s co-defendants was sentenced to

five years’ imprisonment, Betancourt’s lawyer filed a motion with

the state court to reduce his sentence. Id. The state court judge,

“not recalling any sentence reduction agreement and finding no ev-

idence of it on the record, denied the motion.” Id. Betancourt then

moved to withdraw his plea and to recuse the sentencing judge.

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32 Opinion of the Court 20-12206

The sentencing judge voluntarily recused, and another state court

judge held an evidentiary hearing on Betancourt’s motion to with-

draw his plea. The state court ultimately denied his motion. Id.

Betancourt filed a petition for habeas corpus in federal court.

Id. The district court granted his habeas petition based on ineffec-

tive assistance of counsel. The court found that “the representation

of [Betancourt’s] counsel fell below an objective standard of rea-

sonableness by representing to [him] that the court had agreed to

a later sentence reduction, by failing to memorialize the alleged

plea agreement by letter, affidavit or other appropriate means, and

by neglecting to enter it upon the record.” Id. The district court

also found that Betancourt was prejudiced by the defective repre-

sentation. Id. We affirmed on appeal, observing that the evidence

was “uncontroverted that [Betancourt] was completely unaware of

the ultimate consequences of his plea because his counsel misrep-

resented the existence of a sentence reduction agreement.” Id. at

1549.

The circumstances here are far different from those in

Betancourt. As explained above, we are bound to accept the district

court’s finding that Van Vliet never told Riolo there was any bind-

ing agreement between her and the government about his sen-

tence. Therefore, Betancourt is entirely distinguishable. Riolo has

failed to show that Van Vliet provided ineffective assistance of

counsel of the kind we considered in that case.

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20-12206 Opinion of the Court 33

2. Van Vliet’s Miscalculation of Riolo’s Guideline Range

Did Not Amount to Deficient Performance.

Riolo next asserts an ineffective-assistance claim apart from

his challenges to the district court’s findings of fact. He points out

it is undisputed that Van Vliet underestimated his guideline range

by more than 100 months. That alone, he contends, constitutes in-

effective assistance of counsel.

We turn to Strickland’s two-pronged inquiry for assessing

ineffective assistance claims. We must ask whether (1) counsel’s

performance was deficient and if (2) the deficient performance prej-

udiced the movant. See Martin, 949 F.3d at 667 (citing Strickland,

466 U.S. at 687). “Surmounting Strickland’s high bar is never an

easy task, and the strong societal interest in finality has special force

with respect to convictions based on guilty pleas.” Id. (internal quo-

tation marks omitted). Because a § 2255 movant must satisfy both

prongs of Strickland, we need not consider one prong if the defend-

ant fails to satisfy the other. See Holladay v. Haley, 209 F.3d 1243,

1248 (11th Cir. 2000).

Our analysis begins and ends with Strickland’s first prong:

Van Vliet’s performance was not deficient. To show deficient per-

formance, Riolo must establish that Van Vliet’s representation “fell

below an objective standard of reasonableness.” See Martin, 949

F.3d at 667 (internal quotation marks omitted). As an initial matter,

we note that at the time Van Vliet represented Riolo, she was a

criminal lawyer with a great deal of experience with the Sentencing

Guidelines and advising clients about the federal sentencing

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34 Opinion of the Court 20-12206

process. Uncontroverted portions of her testimony indicate she

had been in private practice for 18 or 19 years. Before that, she

worked in the Criminal Division of the Department of Justice and

as an Assistant United States Attorney. Although not determina-

tive, Van Vliet’s experience bolsters the presumption that the qual-

ity of her representation did not fall below the objective standard

of reasonableness. See Provenzano v. Singletary, 148 F.3d 1327,

1332 (11th Cir. 1998) (observing the bolstered presumption of rea-

sonableness where the attorney had been practicing for 20 years).

To be sure, experienced attorneys make mistakes. Van

Vliet’s estimate of Riolo’s guideline range was far off the mark—by

more than 100 months. Riolo points to the Fifth Circuit case of

United States v. Herrera to argue that a petitioner may have a le-

gitimate ineffective-assistance claim when an attorney gives the pe-

titioner incorrect advice regarding his exposure under the Sentenc-

ing Guidelines. See 412 F.3d 577, 580 (5th Cir. 2005) (remanding for

an evidentiary hearing on petitioner’s claim that his counsel under-

estimated his guideline range by 27 months). But we need not de-

cide this issue today. To resolve this appeal, we can assume, with-

out deciding, that a miscalculation of sufficient magnitude can con-

stitute deficient performance and cause prejudice under Strickland.

Ineffective-assistance claims are fact-bound, and here the

well-developed factual record convinces us that Van Vliet’s miscal-

culation was not the product of deficient performance. First of all,

even though Van Vliet estimated Riolo would receive an offense

level of 30 with a range of 97–121 months’ imprisonment, at the

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20-12206 Opinion of the Court 35

same time she warned him that the district court could impose an

additional four-point enhancement for “a violation of commodities

law” while he was “a commodities trading advisor.” U.S. Sent’g

Guidelines Manual § 2B1.1(16)(B)(ii) (U.S. Sent’g Comm’n 2008).

Riolo admitted that “[s]he raised the possibility” that the enhance-

ment might apply. Civ. Doc. 83 at 143. Second, Van Vliet objected

to the enhancement after the probation office produced the PSR.

We cannot say that under these circumstances—where counsel an-

ticipated the enhancement at issue, warned her client that it could

apply, and then objected to its inclusion in the PSR—her perfor-

mance was deficient.

The second four-point enhancement was imposed for “jeop-

ardiz[ing] the safety and soundness of a financial institution.” Id. at

§ 2B1.1(b)(14)(B)(i). Neither Van Vliet nor the government antici-

pated that this enhancement would apply. No doubt this is in part

because our Court had not interpreted it, as both the parties and

the district court observed at sentencing. Van Vliet believed the en-

hancement would not apply because Riolo’s corporations—Ster-

ling and LaSalle—were “fictional” organizations. Crim. Doc. 38 at

4. Because they were not legitimate financial institutions, she ar-

gued, he could not qualify for a sentence enhancement that per-

tained to conduct threatening the safety of legitimate financial in-

stitutions. We are loathe to say that an attorney provided deficient

performance by failing to anticipate the application of a guideline

when the attorney’s reasonable interpretation of that guideline was

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36 Opinion of the Court 20-12206

that it had no bearing on the defendant’s situation and no authori-

tative decision offered guidance to the contrary. 9

To be sure, at the time of Van Vliet’s consultations with Ri-

olo, other circuits had affirmed application of the financial institu-

tion enhancement in circumstances involving sham financial insti-

tutions. See, e.g., United States v. Hoffecker, 530 F.3d 137, 201 (3d

Cir. 2008) (“[T]here is nothing in the guideline to suggest that the

Commission intended to limit the enhancement only to apply to

legitimate financial institutions; we will not read that limitation

into the language of the guideline.”), superseded by regulation on

other grounds as stated in, Rad v. Att’y Gen. United States, 983 F.3d

651, 668 n.13 (3d Cir. 2020); United States v. Collins, 361 F.3d 343,

348 (7th Cir. 2004) (“[W]hen it walks and talks like a financial insti-

tution, even if it’s a phony one, it is . . . covered by [the Guideline].”

(quoting United States v Randy, 81 F.3d 65, 69 (7th Cir. 1996)(em-

phasis in original)); see also United States v. Dale, 374 F.3d 321,

328–330 (5th Cir. 2004) (affirming application of the financial insti-

tution guideline to a fraudulent entity the panel characterized as a

“Ponzi scheme”), vacated on other grounds, 543 U.S. 1113

(2005). 10 But “[t]he test for ineffectiveness is not whether counsel

9 We express no view on the merits of Van Vliet’s argument about the proper

application of the financial institution enhancement.

10 The decisions discussed in this paragraph considered the financial institu-

tion enhancement using the 1997 version of the Sentencing Guidelines. See

Hoffecker, 530 F.3d at 196 n.6.; Collins, 361 F.3d at 345; Dale, 374 F.3d at 327–

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20-12206 Opinion of the Court 37

could have done more; perfection is not required.” Waters v.

Thomas, 46 F.3d 1506, 1518 (11th Cir. 1995) (en banc). Rather, the

question is whether counsel’s representation fell “within the wide

range of reasonable professional assistance.” Id. (internal quotation

marks omitted). Van Vliet anticipated all but one of the sentencing

enhancements the district court ultimately imposed. She double

checked her own work, reaching out to the government to learn of

its calculations. The reasonableness of Van Vliet’s representation is

underscored by the fact that the government independently arrived

at the same guideline calculation. And when the probation office

applied the enhancements, Van Vliet promptly objected. Under

these circumstances, Van Vliet’s performance was far from defec-

tive under Strickland’s standard.

Given our determination that Van Vliet’s conduct met the

objective standard of reasonableness, we have no cause to consider

Strickland’s second prong—prejudice. See Holladay, 209 F.3d at

1248. The district court properly denied Riolo’s § 2255 motion.

28. In the 1997 version, the financial institution enhancement appeared in Part

F. See U.S. Sent’g Guidelines Manual § 2F1.1(b)(6) (U.S. Sent’g Comm’n 1997).

The relevant provision was moved to Part B, but it remained materially un-

changed in the 2008 manual, which was the most recent version available to

Van Vliet at the time of Riolo’s sentencing. See U.S. Sent’g Guidelines Manual

§ 2B1.1(14)(B)(i) (U.S. Sent’g Comm’n 2008).

USCA11 Case: 20-12206 Date Filed: 06/29/2022 Page: 38 of 39

38 Opinion of the Court 20-12206

IV. CONCLUSION

For the above reasons, we affirm the district court’s dismis-

sal of Riolo’s § 2255 motion.

AFFIRMED.

USCA11 Case: 20-12206 Date Filed: 06/29/2022 Page: 39 of 39

20-12206 JORDAN, J., Concurring 1

JORDAN, Circuit Judge, Concurring:

I join Judge Jill Pryor’s comprehensive opinion for the court

in full. I write to point out that the majority of our sister circuits

have held that significant errors in advice about sentencing expo-

sure can, depending on the circumstances, constitute deficient per-

formance. See, e.g., United States v. Mayhew, 995 F.3d 171, 178–

79 (4th Cir. 2021); United States v. Herrera, 412 F.3d 577, 581–82

(5th Cir. 2005); Magana v. Hofbauer, 263 F.3d 542, 550 (6th Cir.

2001); United States v. Gordon, 156 F.3d 376, 380 (2d Cir. 1998);

United States v. Gaviria, 116 F.3d 1498, 1512 (D.C. Cir. 1997);

United States v. Day, 969 F.2d 39, 42–44 (3d Cir. 1992); Iaea v. Sunn,

800 F.2d 861, 864–65 (9th Cir. 1986). Contra United States v. Gor-

don, 4 F.3d 1567, 1570–71 (10th Cir. 1993) (“A miscalculation or

erroneous sentence estimation by defense counsel is not a consti-

tutionally deficient performance rising to the level of ineffective as-

sistance of counsel.”). We have avoided the issue in the past, see

Diveroli v. United States, 803 F.3d 1258, 1263 (11th Cir. 2015), and

do so again today, but we will have to confront it at some point.