United States v. Freeman

19-2432
United States v. Freeman

United States Court of Appeals
For the Second Circuit

August Term 2020

Argued: September 11, 2020
Decided: November 4, 2021

No. 19-2432

UNITED STATES OF AMERICA,

Appellee,

v.

RICO L. FREEMAN,

Defendant-Appellant.

Appeal from the United States District Court
for the Western District of New York
No. 17-cr-162, Lawrence J. Vilardo, Judge.

Before: SULLIVAN, PARK, AND NARDINI, Circuit Judges.

Defendant-Appellant Rico Freeman appeals his conviction following a
guilty plea to a narcotics conspiracy charge in the Western District of New York
(Vilardo, J.). Prior to sentencing, Freeman moved to withdraw his guilty plea on
several grounds, including that the district court misstated the applicable
mandatory minimum term of supervised release in violation of Rule 11 of the
Federal Rules of Criminal Procedure. The district court denied the motion, finding
that the error was harmless in light of the sentencing ranges that Freeman
ultimately faced. On appeal, Freeman argues that the Rule 11 error was not
harmless, that his plea was not knowing or voluntary, and that he received
ineffective assistance of counsel.
Because both parties wrongly assume that the defendant bears the ultimate
burden of persuasion to show that the Rule 11 error affected his substantial rights,
we clarify that where a defendant moved to withdraw a guilty plea before
sentencing based on a Rule 11 error, it is the government’s burden on appeal to
show that such error was harmless. We nevertheless find that Freeman’s
substantial rights were not violated by the Rule 11 error in his plea agreement and
colloquy. Because we conclude that the Rule 11 error was harmless, that
Freeman’s plea was knowing and voluntary, and that Freeman did not receive
ineffective assistance of counsel, we affirm the district court’s judgment in all
respects. AFFIRMED.

BRUCE R. BRYAN, Syracuse, NY, for
Defendant-Appellant.

MONICA J. RICHARDS, Assistant United
States Attorney, for Trini E. Ross, United
States Attorney for the Western District
of New York, Buffalo, NY, for Appellee.

RICHARD J. SULLIVAN, Circuit Judge:

Defendant-Appellant Rico Freeman appeals from a judgment of conviction

entered in the United States District Court for the Western District of New York

(Vilardo, J.) following his guilty plea to one count of conspiring to distribute five

or more kilograms of cocaine and 280 or more grams of cocaine base in violation

of 21 U.S.C. § 846. Prior to sentencing, Freeman moved to withdraw his guilty plea

on several grounds, including that the district court misstated the applicable

2
mandatory minimum term of supervised release in violation of Rule 11 of the

Federal Rules of Criminal Procedure. The district court denied the motion, finding

that the error was harmless in light of the sentencing ranges that Freeman

ultimately faced. On appeal, Freeman argues that the Rule 11 error was not

harmless, that his plea was not knowing or voluntary, and that he received

ineffective assistance of counsel.

Because both parties wrongly assume that Freeman, as the defendant, bears

the ultimate burden of persuasion to show that the Rule 11 error affected his

substantial rights, we clarify that where a defendant moved to withdraw a guilty

plea before sentencing based on a Rule 11 error, it is the government’s burden on

appeal to show that such error was harmless. This clarification is consistent with

the Supreme Court’s guidance in United States v. Vonn, 535 U.S. 55 (2002), which

explains that a preserved challenge to a Rule 11 error is subject to harmless error

review on appeal and that the government bears the burden of showing that the

error had no effect on the defendant’s substantial rights.

While this framework is more defendant-friendly than what the parties

argue in their briefs, we nevertheless find that Freeman’s substantial rights were

not violated by the Rule 11 error in his plea agreement and colloquy and therefore

3
conclude that the error was harmless. For the reasons set forth below, we affirm

the district court’s judgment.

I. BACKGROUND

In August 2017, a grand jury returned an indictment charging Freeman with

one count of conspiracy to distribute five or more kilograms of cocaine and 280 or

more grams of cocaine base in violation of 21 U.S.C. §§ 841(a), 841(b)(1)(A), and

846. The government subsequently filed an information pursuant to 21 U.S.C.

§ 851 to establish Freeman’s prior felony drug conviction, which had the effect of

raising Freeman’s mandatory minimum term of imprisonment from 10 to 20 years

and his mandatory minimum term of supervised release from five to 10 years.

In May 2018, Freeman pleaded guilty to the indictment pursuant to a plea

agreement with the government. The plea agreement accurately reflected that

Freeman faced a mandatory minimum term of imprisonment of 20 years and a

maximum term of imprisonment of life, and that he faced a maximum term of

supervised release of life. The agreement incorrectly stated, however, that

Freeman was subject to a statutorily prescribed mandatory minimum term of five,

rather than 10, years of supervised release. The agreement also provided that the

Guidelines range for supervised release was five years to life, when in fact the

4
correct Guidelines range was 10 years to life.

The error in the agreement carried over to Freeman’s plea allocution. While

the district court accurately stated both the minimum and maximum terms of

imprisonment that Freeman faced, it wrongly stated that the mandatory minimum

term of supervised release was five years. After this misstatement, however, the

district court correctly told Freeman that it could sentence him to a life term of

supervised release, and Freeman acknowledged that he understood.

In early August, the Probation Department filed a Presentence Investigation

Report (“PSR”) in preparation for sentencing. Contrary to the plea agreement, the

PSR accurately stated that Freeman faced a mandatory minimum term of

supervised release of 10 years. On September 4, 2018, Freeman filed a statement

affirming that he had no objection to the PSR’s factual or legal findings. At that

time, Freeman made no mention of the incorrect mandatory minimum term of

supervised release referenced in the plea agreement and during the plea colloquy,

and made no attempt to withdraw his plea.

On September 10, 2018 – the date that sentencing was scheduled to occur –

the district court acknowledged the plea agreement’s error regarding the

minimum supervised release term. The court adjourned sentencing to allow

5
counsel to speak with Freeman. Three days later, at a status conference, Freeman

requested an opportunity to withdraw his plea. According to counsel, Freeman

had indicated “that he thinks that the legal basis [for withdrawal] is ineffective

assistance of counsel, namely that [counsel] should have caught the error that the

[c]ourt found” concerning the mandatory term of supervised release, as well as a

miscalculation regarding Freeman’s criminal history. App’x at 78. The district

court stated that it did not “see any basis for concluding . . . that there was any

ineffective assistance,” noting that although correction of the Rule 11 error

“changes the mandatory minimum in terms of supervised release, it probably

wouldn’t have changed the term of supervised release at all in terms of the

sentence that [the court] would have imposed.” Id. at 81. Nevertheless, the district

court told Freeman that he could file a motion to withdraw his plea, and it

ultimately appointed new counsel to help him file that motion and advise him on

whether previous counsel had been ineffective.

After seeking and receiving multiple extensions of time, Freeman moved to

withdraw his plea on February 18, 2019. He insisted that he had “relied in part on

the terms of the plea agreement,” including the mistake of law regarding the

mandatory minimum term of supervised release, in deciding to plead guilty. Id.

6
at 123. He also asserted a “claim of innocence” and argued that he “felt coerced

into taking a plea to help secure [his girlfriend’s] release [from custody] and also

help her to avoid incarceration upon the resolution of her case.” Id. at 113–18.

The government opposed the motion, arguing that the Rule 11 error did not

constitute a “fair and just” reason to permit withdrawal of Freeman’s plea. Id. at

144. The government argued that the misstatement of the mandatory minimum

term of supervised release constituted merely harmless error in light of the

maximum penalties Freeman knew that he faced. Id. at 144–45 (discussing the

Seventh Circuit’s holding in United States v. Saenz, 969 F.2d 294 (7th Cir. 1992), that

a misstatement of the minimum mandatory term of supervised release was

harmless where the maximum term was life). Further, the government noted that

the length of Freeman’s total sentence was ultimately unchanged because the

intervening passage of the First Step Act in December 2018 reduced his mandatory

minimum term of imprisonment from 20 to 15 years, resulting in a combined

mandatory minimum sentence of 25 years – the same total set forth in the plea

agreement, though with a different distribution among the component parts. 1

1The First Step Act amended 21 U.S.C. § 841(b)(1)(A) to lower the mandatory minimum sentence
from 20 years to 15 years for recidivists who commit certain drug offenses. Pub. L. No. 115-391,
§ 401(c), 132 Stat. 5194, 5221 (2018).

7
 At oral argument on Freeman’s motion, the district court sought to

understand the impact of the Rule 11 error on Freeman’s plea. Citing the effect of

the First Step Act in reducing Freeman’s mandatory minimum term of

imprisonment, the court asked defense counsel how the misstatement of the

mandatory minimum term of supervised release “would have made a material

difference to [Freeman] in deciding whether to plead guilty[.]” App’x at 156.

Freeman’s counsel – who was appointed for the purpose of making the motion to

withdraw – responded, “I don’t know that it would, Judge, but we don’t know

that.” Id.

A few weeks later, the district court denied Freeman’s motion to withdraw

his guilty plea. First, the court found that Freeman’s own sworn statements during

his plea colloquy – including his admission that he knew that the narcotics

conspiracy to which he was pleading guilty involved at least five kilograms of

cocaine and 280 grams of cocaine base – contradicted his claim of legal innocence.

Second, the district court found that Freeman’s sworn responses to the court’s

various questions at his plea colloquy also refuted any argument that he had been

coerced into pleading guilty against his will.

Finally, the court considered Freeman’s argument that the misstatement of

8
the mandatory minimum term of supervised release in his plea agreement and

during the plea colloquy rendered his plea not knowing and voluntary and thus

constituted a fair and just reason for withdrawal. The court’s analysis ultimately

focused on whether that mistake was harmless. Relying on the Seventh Circuit’s

holding in Saenz, the district court first noted that the 10-year mandatory

minimum supervised release term was well within the articulated range of five

years to life and therefore, at the time of his plea, Freeman “was fully aware that

he could be sentenced to ten years of supervised release or more.” Id. at 184.

The district court also agreed with the government that because the First

Step Act reduced Freeman’s mandatory minimum term of imprisonment from 20

to 15 years, “the combined total [mandatory] sentence of imprisonment and

supervised release” remained unchanged. Id. at 185 (quoting United States v.

Andrades, 169 F.3d 131, 134 (2d Cir. 1999) (internal quotation marks omitted)).

Indeed, the district court observed that the error in the plea agreement and Rule

11 colloquy had the fortuitous effect of delaying Freeman’s sentencing and

enabling him to take advantage of the more favorable terms set forth in the First

Step Act. 2 The court saw “no reasonable argument that Freem[a]n would not have

2As noted above, the First Step Act reduced by five years the mandatory minimum sentence for
recidivists who commit certain drug offenses. For offenses committed before the First Step Act’s

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pleaded guilty if he knew then what he knows now.” Id. at 186. The district court

thus agreed with the government, concluding that the error in the plea agreement

was “no more than ‘a minor and technical violation of Rule 11 which amounts to

harmless error,’” and that “there [was] no fair and just reason to allow Freeman to

withdraw his guilty plea.” Id. (quoting Andrades, 169 F.3d at 133).

On June 14, 2019, the district court sentenced Freeman to 15 years’

imprisonment and 10 years’ supervised release, the minimum total sentence

allowed by law. Freeman timely appealed.

II. DISCUSSION

On appeal, Freeman argues that the district court should have granted his

motion to withdraw his guilty plea. He principally contends that the district

court’s misstatement of the mandatory minimum term of his supervised release

was not harmless. He further asserts that this Rule 11 error – in tandem with other

purported errors relating to the factual basis for the plea and his allegation that the

government threatened to prosecute his girlfriend for witness tampering if he did

enactment, the reduced mandatory minimum sentence applies only “if a sentence for the offense
has not been imposed as of such date of enactment.” Pub. L. No. 115-391, § 401(c), 132 Stat. 5194,
5221 (2018). Because the district court pointed out the Rule 11 error to Freeman on the day that
he was originally to be sentenced, and then gave him substantial time to consider withdrawing
his plea, the court did not impose Freeman’s sentence until after the Act had taken effect.

10
not plead guilty – prevented him from making a knowing and voluntary guilty

plea. Finally, Freeman argues that he received ineffective assistance of counsel.

Before we address the merits of these arguments, we must first clarify the

applicable framework and standard of review on appeal where a defendant asserts

a Rule 11 error.

A. Where the defendant identified a Rule 11 error before sentencing, the
government bears the burden on appeal of showing that the error is harmless.

Prior to sentencing, Freeman moved to withdraw his plea based on the Rule

11 error identified by the district court, thereby preserving his challenge on appeal.

The parties presume to apply different standards of appellate review to this

challenge. The government argues that we should apply an abuse of discretion

standard and place the burden of persuasion on Freeman. For his part, Freeman

likewise places the burden of persuasion on himself but argues for a harmless error

standard. A closer look at our precedent establishes that both parties’ proposed

standards are incorrect.

Rule 11 of the Federal Rules of Criminal Procedure “sets forth requirements

for a plea allocution and ‘is designed to ensure that a defendant’s plea of guilty is

a voluntary and intelligent choice among the alternative courses of action open to

the defendant.’” Andrades, 169 F.3d at 133 (citation omitted). Rule 11(d) provides

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that “[a] defendant may withdraw a plea of guilty or nolo contendere . . . after the

court accepts the plea, but before it imposes sentence if,” as relevant here, “the

defendant can show a fair and just reason for requesting the withdrawal.”

Nevertheless, while a district court’s failure to correctly provide the defendant

with all the information required by Rule 11 may constitute a “fair and just reason”

to request the withdrawal of a guilty plea, Rule 11(h) makes clear that such a

failure does not automatically require return of a defendant’s guilty plea. Rather,

“[a] variance from the requirements of” Rule 11 may be disregarded as harmless

error when it “does not affect substantial rights.” Fed. R. Crim. P. 11(h); see United

States v. Ferrara, 954 F.2d 103, 106 (2d Cir. 1992) (explaining that “[s]ection (h) was

added to Rule 11 . . . to make clear that guilty pleas ‘should not be overturned,

even on direct appeal, when there has been a minor and technical violation of Rule

11 which amounts to harmless error’” (citation omitted)).

It is true that, generally, we review a district court’s denial of a motion to

withdraw a guilty plea for abuse of discretion. See United States v. Adams, 448 F.3d

492, 498 (2d Cir. 2006). But that is not the case when the motion to withdraw is

based on an alleged failure to provide sufficient Rule 11(b) warnings prior to the

plea. As the Supreme Court explained in United States v. Vonn, when a reviewing

12
court considers a preserved challenge to a Rule 11 error, the government bears the

burden of proving that the error was harmless. 535 U.S. at 58. And since the Vonn

harmless error standard applies on appeal when a defendant has objected in

district court, it follows logically that it must also apply when the defendant

moved to withdraw his guilty plea based on an alleged Rule 11 violation. See

United States v. Yang Chia Tien, 720 F.3d 464, 469 (2d Cir. 2013) (reviewing for

harmlessness where defendant raised a Rule 11 argument in a pro se motion to

withdraw his plea in district court); United States v. Gonzalez, 420 F.3d 111, 131 (2d

Cir. 2005) (stating that although district courts “enjoy considerable discretion in

ruling on motions to withdraw guilty pleas,” such motions must be granted “when

a defendant was not provided with the ‘mix of information’ required by Rule 11

unless, of course, the error can be deemed harmless because it would not have

affected the defendant’s decision to plead guilty” (citation omitted)).

To be sure, our past decisions reviewing the denial of a defendant’s motion

to withdraw based on an alleged Rule 11 error have not always been consistent or

a model of clarity. Compare United States v. Harrington, 354 F.3d 178, 183–84 (2d

Cir. 2004) (stating, when reviewing the denial of a defendant’s motion to withdraw

based on a Rule 11 error, that “the defendant has the burden of showing that a

13
district court’s error had an effect on his decision to plead guilty” (internal

quotation marks, citation, and alterations omitted)), with Yang Chia Tien, 720 F.3d

at 469, and United States v. McCutcheon, 765 F. App’x 507, 510 n.1 (2d Cir. 2019)

(explaining that defendant “preserved his Rule 11(b)(2) challenge by moving to

withdraw his plea” in part based on Rule 11 error, so the Court would review that

challenge for harmless error, placing the burden of persuasion on the

government). Freeman’s confusion in the present case likely stems from his

reliance on Harrington, a decision that appears to have overlooked Vonn (handed

down two years earlier) and instead applied a conflicting standard from a pre-

Vonn Second Circuit case, United States v. Harrison, 241 F.3d 289, 293 (2d Cir. 2001).

Nevertheless, after Harrington adopted the standard from Harrison – a standard

clearly at odds with Vonn – a subsequent Supreme Court case, United States v.

Dominguez Benitez, 542 U.S. 74, 81 n.7 (2004), reiterated the Vonn standard and thus

cast doubt on Harrington’s deviation from prior Supreme Court precedent.

Our more recent case law follows the standard reiterated in Dominguez

Benitez. See, e.g., Yang Chia Tien, 720 F.3d at 469 (citing Dominguez Benitez, 542 U.S.

at 81 n.7); see also United States v. Johnson, 850 F.3d 515, 522 (2d Cir. 2017) (citing the

relevant standard from Yang Chia Tien); United States v. Vaval, 404 F.3d 144, 151 n.3

14
(2d Cir. 2005). We therefore conclude that intervening Supreme Court and Second

Circuit precedent requires us to reject the standard applied in Harrington. See

Finkel v. Stratton Corp., 962 F.2d 169, 174–75 (2d Cir. 1992) (recognizing that

generally, “one panel of this court may not overrule the decision of a prior panel,”

but “that [this] rule does not apply where an intervening Supreme Court decision

casts doubt on the prior ruling”).

Whatever the source of the past confusion, we now make clear that where a

defendant identified a Rule 11 error in moving to withdraw his guilty plea below,

the government bears the burden on appeal of showing, based on the entire record,

that the error did not affect the defendant’s substantial rights. See Johnson, 850 F.3d

at 522 (explaining that where defendant raised a Rule 11 violation in district court,

the government “must prove that the error was harmless beyond a reasonable

doubt” (internal quotation marks omitted)); Yang Chia Tien, 720 F.3d at 469; see also

Dominguez Benitez, 542 U.S. at 80 (noting that reviewing courts must consult the

whole record when considering the effect of a Rule 11 error on substantial rights).

B. The government has proven that, in light of the entire record, the Rule 11
error did not affect Freeman’s substantial rights.

Having clarified the applicable standard, we now turn to Freeman’s plea.

The district court in this case determined that even if Freeman had been informed

15
of the correct mandatory minimum term of supervised release, he still would have

pleaded guilty. We reach the same conclusion and find that the government has

carried its burden of showing that the district court’s misstatement of Freeman’s

mandatory minimum term of supervised release was harmless.

As the government points out in its brief, Freeman expressly acknowledged

before his guilty plea that he faced a potential life term of supervised release.

Moreover, prior to sentencing, Freeman voiced no objection to the PSR, which

correctly stated that he faced a mandatory minimum term of supervised release of

10 years and a maximum term of supervised release of life. And while Freeman

now maintains that the district court’s misstatement of his mandatory minimum

term of supervised release “strong[ly] induce[d]” his guilty plea, Freeman Br. at

41 (citation omitted), statements on the record by Freeman’s counsel – and

Freeman himself – belie Freeman’s arguments about the significance of the Rule

11 error. Indeed, at oral argument on Freeman’s motion to withdraw, his counsel

said that he did not know if the Rule 11 error “made a material difference” to

Freeman’s plea decision. App’x at 156. And at the time of Freeman’s sentencing,

after the district court denied his motion to withdraw his plea, Freeman personally

addressed the court and asserted that he decided to plead guilty not because of the

16
court’s misstatement of the mandatory minimum term of supervised release, but

because of the government’s purported threats to prosecute his girlfriend. As

Freeman stated before the district court:

I just want it [to] be known on the record that if my
child’s mother would have never got arrested, which the
case is dismissed now because I signed that plea
agreement, I had full intentions of going to trial knowing
that [the government] would never have proved 5
kilograms or 280 grams of cocaine base.

Id. at 198.

These statements on the record, along with the fact that Freeman fully

understood that he faced a potential life term of supervised release at the time of

his plea and made no objections to the corrected statement of his mandatory

minimum term of supervised release when it appeared in the PSR, demonstrate

beyond a reasonable doubt that Freeman would have entered his plea regardless

of the Rule 11 error. Accordingly, based on the record before us, we find that the

district court’s misstatement as to the mandatory minimum term of supervised

release did not affect Freeman’s substantial rights, see Vonn, 535 U.S. at 58, 74, and

that the error was therefore harmless.

C. Freeman’s additional challenges to the voluntariness of his plea are directly
contradicted by the record.

17
 Freeman raises additional arguments to suggest that his plea was

involuntary, including assertions that (1) he was confused as to the factual basis

for the drug quantities attributable to him, (2) he is innocent of the crime of which

he was convicted, and (3) the government coerced his plea by threatening to

prosecute his girlfriend. To the extent that Freeman’s additional challenges are

unrelated to any Rule 11 error and are offered as “independent ground[s]” to

justify his attempt to withdraw his plea, Freeman Br. at 63, we review those

challenges under an abuse of discretion standard and review any related findings

of fact for clear error. See United States v. Rivernider, 828 F.3d 91, 104 (2d Cir. 2016);

see also United States v. Peterson, 248 F.3d 79, 82 (2d Cir. 2001) (explaining that a

district court abuses its discretion “if it base[s] its ruling on an erroneous view of

the law or a clearly erroneous assessment of the evidence” (quoting United States

v. Doe, 79 F.3d 1309, 1319–20 (2d Cir. 1996))).

Freeman asserts that the record reflects “confusion” as to whether he

“knowingly and voluntarily admitted to the drug quantity claimed by the

government at the plea proceeding” because the government was vague in

representing to the district court how it would prove the drug amounts. Freeman

Br. at 63. But the record from Freeman’s plea proceeding clearly refutes his

18
contention that the answers he gave – under oath – concerning the drug amounts

involved in his offense were “simply acknowledg[ments] that the [g]overnment

had claimed it would offer proof of that amount at trial.” Freeman Br. at 60.

At the plea proceeding, the district court asked Freeman a series of clear and

direct questions to which he responded affirmatively before admitting his guilt.

Among other things, the court asked Freeman whether he was “pleading guilty

because [he] did the things that the plea agreement sa[id he] did and that are

charged in the indictment,” App’x at 51, to which Freeman replied, “Yes,” id. The

court then asked Freeman whether “at least 5 kilograms of cocaine [were]

reasonably foreseeable to [him] as being within the scope” of his agreement to

“commit a controlled substance felony offense.” Id. at 51–52. Freeman replied,

“Yes.” Id. at 52. Finally, the court asked Freeman whether “at least 280 grams of

cocaine base [were] reasonably foreseeable to [him] as being within the scope” of

that same agreement. Id. Once again, Freeman said, “Yes.” Id.

We find no ambiguity in the court’s questions or in Freeman’s answers,

which clearly supported the district court’s decision to accept Freeman’s guilty

plea. These admissions during Freeman’s plea proceeding create “a formidable

barrier” to challenging the validity of his plea, Blackledge v. Allison, 431 U.S. 63, 74

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(1977), and Freeman’s “bald statements that simply contradict what he said at his

plea allocution are not sufficient grounds to withdraw the guilty plea” and may

be rejected summarily, United States v. Torres, 129 F.3d 710, 715 (2d Cir. 1997). In

short, the record reflects no confusion as to the factual basis of Freeman’s plea and

undermines any assertion of actual innocence by Freeman on appeal.

Freeman’s argument that the government coerced his plea by arresting and

prosecuting the mother of his child for witness tampering is equally unpersuasive.

As reflected in the record, Freeman made sworn statements during his colloquy

affirming that he was pleading guilty “voluntarily and of [his] own free will,”

without the pressure of any force or threat. App’x at 36 (attesting that no one had

“attempted in any way to threaten [him], threaten a family member, [or] threaten

anyone close to [him] to make [him] plead guilty”). Freeman offers no evidence

to counter these statements, which again “carry a strong presumption of verity.”

Blackledge, 431 U.S. at 74. We therefore have no reason to discount them in favor

of Freeman’s subsequent unsupported allegations.

D. Freeman’s ineffective assistance of counsel challenge fails because he was
not prejudiced by the errors that he alleges.

Finally, Freeman challenges his plea on the grounds that he received

ineffective assistance of counsel. Specifically, Freeman asserts that his retained

20
counsel’s performance was deficient because counsel (1) failed to identify and

correct the Rule 11 error in Freeman’s plea agreement and allocution, and (2)

“failed to ascertain that Freeman was overcharged in the [i]ndictment because the

government’s evidence did not support the allegation that he distributed five

kilograms or more of cocaine and 280 grams or more of cocaine base.” Freeman

Br. at 31. These arguments, which are really just variations on the arguments

discussed above, fail upon review of the record.

When “a defendant is represented by counsel during the plea process and

enters his plea upon the advice of counsel, the voluntariness of the plea depends

on whether counsel’s advice ‘was within the range of competence demanded of

attorneys in criminal cases.’” Hill v. Lockhart, 474 U.S. 52, 56 (1985) (citation

omitted). The two-pronged standard for evaluating ineffective assistance claims

requires Freeman to “show that [his] counsel’s representation fell below an

objective standard of reasonableness,” Strickland v. Washington, 466 U.S. 668, 688

(1984), and that “there is a reasonable probability that, but for counsel’s

unprofessional errors, the result of the proceeding would have been different,” id.

at 694. Of course, we need not consider the Strickland components “in the same

order or even . . . address both components of the inquiry if the defendant makes

21
an insufficient showing on one.” Id. at 697. In other words, we are not required

to “determine whether counsel’s performance was deficient before examining the

prejudice suffered by the defendant as a result of the alleged deficiencies.” Id.

When considering prejudice in the plea context, we “inquire[] into the record as a

whole to determine whether a reasonable probability exists that[,] absent counsel’s

error,” the defendant “would have proceeded to trial rather than plead guilty.”

United States v. Arteca, 411 F.3d 315, 321 (2d Cir. 2005).

With respect to Freeman’s ineffective assistance claim based on the Rule 11

error, we conclude that, regardless of whether his counsel committed error in

failing to raise that issue before his plea, Freeman cannot now show that he was

prejudiced by that failure. Because we have already considered the entire record

and found that the government has proven beyond a reasonable doubt that

Freeman would still have pleaded guilty even if counsel had identified the Rule

11 error, Freeman cannot possibly establish that he was prejudiced by his counsel’s

alleged error.

Similarly, Freeman’s own sworn statements contradict his current insistence

that his lawyer should have known that the indictment overstated the drug

quantities attributable to him. During his guilty plea, Freeman expressly

22
acknowledged that more than five kilograms of cocaine and 280 grams of cocaine

base were “reasonably foreseeable to [him] as being within the scope” of his

agreement to “commit a controlled substance felony offense.” App’x at 51–52.

While Freeman now questions the government’s ability to prove those amounts

had he gone to trial, he does not contend that his sworn statements were false, or

that his lawyer knew them to be false, at the time of his guilty plea. See Torres, 129

F.3d at 715 (affirming denial of motion to withdraw guilty plea where defendant’s

“unequivocal admissions under oath contradict[ed] his unsupported assertions of

pressure”). On this record, Freeman has failed to establish that his counsel’s

representation fell below an objective standard of reasonableness, or that he was

prejudiced by it. That failure is fatal to his ineffective assistance argument. 3

III. CONCLUSION

For the foregoing reasons, we AFFIRM the judgment of the district court.

3Whether we consider Freeman’s challenges to the voluntariness of his plea as separate grounds
for withdrawal of his plea, see supra at 18–24, or additional arguments relevant to our Rule 11
analysis of harmlessness, the result is the same. Under any of the potentially applicable standards
of review, the record before us is clear and contradicts Freeman’s assertions that he should be
permitted to withdraw his plea.

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