United States Court of Appeals

FOR THE DISTRICT OF COLUMBIA CIRCUIT

Decided June 9, 2009

No. 08-3017

UNITED STATES OF AMERICA,

APPELLEE

v.

FRANK BERKELEY,

APPELLANT

Appeal from the United States District Court

for the District of Columbia

(No. 06cr00208-01)

Billy L. Ponds filed a brief for appellant. Frank Berkeley,

pro se, filed supplemental briefs for appellant.

Jeffrey A. Taylor, U.S. Attorney at the time the brief was

filed, and Roy W. McLeese III, Mary B. McCord, and J.P.

Cooney, Assistant U.S. Attorneys, were on the briefs for

appellee.

Before: GARLAND and BROWN, Circuit Judges, and

WILLIAMS, Senior Circuit Judge.

Opinion for the Court filed by Circuit Judge GARLAND.
2

1

This case was considered on the record from the United States

District Court for the District of Columbia and on the briefs filed by

the parties. See FED. R. APP. P. 34(a)(2); D.C. CIR. R. 34(j).

GARLAND, Circuit Judge: Frank Berkeley agreed to plead

guilty to a single count of distributing cocaine base. In

exchange, the government agreed to drop a second count and to

ensure that Berkeley would not be prosecuted for possession of

a gun and drugs found at the scene of his arrest. Before

sentencing, Berkeley moved to withdraw his plea, arguing that

his lawyer failed to inform him of an entrapment defense

because of a conflict of interest, and that the lawyer’s advice

concerning his eligibility for early release constituted ineffective

assistance of counsel. After an evidentiary hearing, the district

court denied the motion and sentenced Berkeley to 169 months

in prison. On appeal, Berkeley contends that the denial of his

motion was an abuse of discretion, and that the imposition of his

sentence was flawed. We reject these contentions and affirm the

judgment of the district court.1

I

On August 2, 2005, Harold Holden called Berkeley to

inquire about purchasing approximately 62 grams of cocaine

base (“crack”). Berkeley knew Holden to be the father of

Berkeley’s girlfriend, but did not know that Holden was also a

government informant. Moments after receiving Holden’s call,

Berkeley met him in the 1000 block of 44th Street, N.E. in

Washington, D.C., and exchanged approximately 62 grams of

crack for $1900 in cash. The transaction was video- and audiotaped by agents of the Drug Enforcement Administration

(DEA).

On September 21, 2005, Berkeley contacted Holden

regarding an additional transaction for a similar quantity of
3

crack. The two met in the 1700 block of Benning Road, N.E.,

where Holden introduced Berkeley to an undercover agent.

Berkeley gave the agent approximately 62 grams of crack in

exchange for $1700. The DEA again taped the transaction. As

Berkeley conceded before the district court, “the videotapes and

audiotapes unequivocally identified Berkeley as the person

involved in both transactions.” Def.’s Post-Hr’g Br. 1.

Based on these two transactions, a federal grand jury in the

District of Columbia returned a two-count indictment, charging

Berkeley with unlawful distribution of 50 grams or more of

cocaine base in violation of 21 U.S.C. § 841(a)(1) and

(b)(1)(A)(iii). An arrest warrant was issued, and on July 19,

2006, Berkeley was arrested outside his residence in Landover

Hills, Maryland, as he attempted to enter a car registered to his

stepfather. During the search incident to his arrest, agents found

approximately 31 grams of suspected crack in Berkeley’s

pocket, as well as a 9mm handgun and $91,980 in cash in the

vehicle.

Attorney Douglas Wood was Berkeley’s first lawyer in the

U.S. District Court, and he negotiated a plea agreement on

Berkeley’s behalf. Wood had represented Berkeley in three

previous felony cases, two of which were dismissed and one of

which resulted in misdemeanor convictions for drug possession.

In a fourth case in 2000, Berkeley faced Maryland drug charges

together with co-defendant Dennis Butler. In that case, Wood

represented Butler while another attorney represented Berkeley.

On September 29, 2006, following a plea hearing under

Rule 11 of the Federal Rules of Criminal Procedure, Berkeley

pled guilty to Count One of the indictment. In return for the

plea, the government agreed to dismiss the remaining count. It

also pledged to secure declination letters from the Maryland

State’s Attorney’s Office and the United States Attorney’s
4

Office for the District of Maryland, agreeing not to prosecute

Berkeley for the gun and drugs found at the time of his arrest.

Plea Agreement ¶ 5.

The parties stipulated that a sentence within the applicable

U.S. Sentencing Guidelines range would be reasonable in light

of the statutory sentencing factors. Id. ¶ 10. The government

agreed that a 3-level decrease in Berkeley’s Guidelines offense

level would be appropriate, pursuant to U.S.S.G. § 3E1.1,

“[a]ssuming [Berkeley] clearly demonstrates acceptance of

responsibility” for his offense. Id. ¶ 9. The agreement expressly

reserved the government’s right “to seek denial of the

adjustment for acceptance of responsibility . . . should

[Berkeley] move to withdraw [his] guilty plea after it is

entered.” Id. ¶ 11.

On February 2, 2007, after replacing Wood as counsel,

Berkeley moved to withdraw his guilty plea pursuant to Federal

Rule of Criminal Procedure 11(d). His principal contention was

that Wood, because of a conflict of interest, had failed to advise

him that he had an entrapment defense. Berkeley also

contended that Wood had wrongly advised him that he would be

placed in a Bureau of Prisons (BOP) drug treatment program

that would allow his release from prison a year early. 

The district court held an evidentiary hearing to address

Berkeley’s claims. According to Berkeley’s testimony, Holden

had sent him a letter demanding that he take part in the two drug

transactions and threatening bodily harm to Berkeley and his

family if he did not comply. This threat scared Berkeley, as

Holden was “three times his size,” Mot. Hr’g Tr. 16 (Aug. 9,

2007), and it was because of this threat from a government

informant that Berkeley engaged in the drug deals. Berkeley

testified that, although he told Wood about the letter, Wood said

that Berkeley could not win the case and should agree to the
5

government’s plea offer. Berkeley further maintained that the

reason Wood did not advise him that he had an entrapment

defense was that such a defense would have required Wood to

withdraw from the representation. According to Berkeley, the

government would have attempted to counter the entrapment

defense by showing that he was predisposed to commit the

crime -- and would have done so by calling for the testimony of

the co-defendant in his 2000 drug case, Butler, whom Wood had

represented.

Wood had a different account of his representation of

Berkeley. He testified that Berkeley “never told [him] he had

[been] threatened by Mr. Holden,” and that he “was not aware

of any letter from Mr. Holden to Mr. Berkeley.” Id. at 123.

Faced with a strong case against his client and what he assessed

as an attractive offer from the government, Wood advised

Berkeley to accept the plea agreement. In so doing, however, he

warned Berkeley that he faced at least a 10-year mandatory

minimum sentence. Wood said that he made no promises as to

what the ultimate sentence would be, but that he advised

Berkeley that he “could get maybe . . . six months to a year off

as a result of a drug treatment program while incarcerated” if

“the court recommended a drug treatment program and he was

accepted” into it. Id. at 115. As Wood explained on the record

at Berkeley’s plea hearing, he also warned Berkeley that,

because he was not a U.S. citizen, his conviction could result in

deportation, although “[t]here [was] no INS detainer” at the

time. Plea Hr’g Tr. 6 (Sept. 29, 2006).

On October 16, 2007, the district court denied Berkeley’s

motion. United States v. Berkeley, 515 F. Supp. 2d 159 (D.D.C.

2007). The court credited Wood’s testimony that Berkeley had

never informed Wood of Holden’s letter, and hence that Wood

had no reason to believe that Berkeley had an entrapment

defense. Wood’s advice to plead guilty, the court found, was
6

based on his judgment that “[g]iven the strength of the

Government’s case, and the Defendant’s prior drug activities,

. . . trial was not in the Defendant’s best interest because of the

heavy sentence he would most probably receive.” Id. at 163.

The court also found that, although Wood advised Berkeley that

early release was possible if BOP placed him in a drug treatment

program, he made no “promises that this would occur or that this

was a statutory entitlement.” Id. at 165.

The case then proceeded to sentencing. The U.S. Probation

Office prepared a Presentence Investigation Report (PSR) that

initially calculated Berkeley’s total offense level as 34 and

placed him in criminal history category III. PSR at 21. The

calculation was based on a base offense level of 30, see U.S.S.G.

§ 2D1.1(c)(5), a 2-level enhancement for obstruction of justice,

see id. § 3C1.1, and an additional 2-level enhancement for

possession of a weapon, see id. § 2D1.1(b)(1). PSR at 6. The

PSR did not incorporate a reduction for acceptance of

responsibility because Berkeley had moved to withdraw his

guilty plea, and because an enhancement for obstruction of

justice is generally inconsistent with a reduction for acceptance

of responsibility. See id. (citing U.S.S.G. § 3E1.1 cmt. n.4).

At the February 12, 2008, sentencing hearing, both parties

agreed that the enhancement for possession of a weapon was

inappropriate and that Berkeley’s Guidelines level was at most

32. Berkeley argued for an additional 3-level reduction for

acceptance of responsibility, but the district court rejected that

argument. It found that “[t]he motion to withdraw a guilty plea

in and of itself is a statement that Mr. Berkeley did not wish to

let the guilty plea stand, and therefore, he didn’t wish to accept

responsibility for this offense,” and that the reduction was also

unwarranted because of Berkeley’s false statements at the

evidentiary hearing. Sentencing Hr’g Tr. 13-14 (Feb. 12, 2008).

The court therefore calculated the offense level to be 32 and the
7

2

Although an entrapment defense may form the basis for a viable

claim of innocence, see Hanson, 339 F.3d at 988, Berkeley instead

applicable Guidelines range to be 151-188 months. Id. at 14.

The court imposed a sentence of 169 months’ imprisonment,

followed by five years of supervised release. Id. at 18.

Berkeley filed a notice of appeal on February 19, 2008.

Initially, Berkeley’s briefs, prepared by counsel, addressed only

the district court’s denial of his motion to withdraw his plea.

We subsequently granted Berkeley leave to file a pro se

supplemental brief, in which he challenged the district court’s

calculation of his Guidelines range. United States v. Berkeley,

No. 08-3017, Order (D.C. Cir. Sept. 26, 2008). We address both

issues below.

II

A defendant may withdraw a guilty plea prior to sentencing

if he “can show a fair and just reason for requesting the

withdrawal.” FED. R. CRIM. P. 11(d)(2)(B). Although

“[w]ithdrawal of a guilty plea prior to sentencing is to be

liberally granted,” United States v. Taylor, 139 F.3d 924, 929

(D.C. Cir. 1998), we review a district court’s refusal to permit

withdrawal only for abuse of discretion, United States v.

Hanson, 339 F.3d 983, 988 (D.C. Cir. 2003). “In reviewing

such a refusal, we consider three factors: ‘(1) whether the

defendant has asserted a viable claim of innocence; (2) whether

the delay between the guilty plea and the motion to withdraw

has substantially prejudiced the government’s ability to

prosecute the case; and (3) whether the guilty plea was somehow

tainted.’” United States v. Curry, 494 F.3d 1124, 1128 (D.C.

Cir. 2007) (quoting Hanson, 339 F.3d at 988). In this appeal,

Berkeley does not assert that he has a viable claim of

innocence,2

 and the government does not suggest that it would
8

bases his appeal on the claim that his plea was tainted by his lawyer’s

conflict and ineffectiveness. He alleges an entrapment defense only

to further his conflict argument.

be prejudiced by being forced to go to trial. We therefore focus

our review on the third factor -- which we have described as the

“‘most important.’” Taylor, 139 F.3d at 929 (quoting United

States v. Ford, 993 F.2d 249, 251 (D.C. Cir. 1993)).

Berkeley’s claim that his plea was tainted is premised on

what he says was ineffective assistance of counsel, a deficiency

that can render a plea involuntary. See Hanson, 339 F.3d at 990.

Such a challenge to a guilty plea “must be evaluated under the

general test for ineffective assistance set forth in Strickland v.

Washington, 466 U.S. 668 (1984).” Curry, 494 F.3d at 1129

(citing Hill v. Lockhart, 474 U.S. 52, 58 (1985)). Ordinarily,

this requires two showings by the defendant: “that counsel’s

performance was deficient . . . [and] that the deficient

performance prejudiced the defense.” Id. (quoting Strickland,

466 U.S. at 687). Under Cuyler v. Sullivan, however,

“[p]rejudice is presumed . . . if the defendant demonstrates that

counsel ‘actively represented conflicting interests’ and that ‘an

actual conflict of interest adversely affected his lawyer’s

performance.’” Strickland, 466 U.S. at 692 (quoting Cuyler v.

Sullivan, 446 U.S. 335, 348, 350 (1980)). 

Berkeley alleges two deficiencies in his trial counsel’s

performance. First, he maintains that Wood labored under a

conflict of interest, thus implicating the less demanding Cuyler

standard. Second, he claims that Wood misadvised him

concerning his eligibility for early release, a claim that requires

Berkeley to meet both prongs of the Strickland test. We

consider each argument in turn.
9

Berkeley’s conflict-of-interest argument is based on the

following chain of logic: Berkeley told Wood that he engaged

in the crack transaction because Harold Holden, who was

cooperating with the government, had threatened him. Berkeley

therefore had an entrapment defense that Wood failed to pursue.

Wood failed to pursue this defense because he knew that the

government, in order to establish predisposition to commit the

crime and thereby defeat the defense, see Hanson, 339 F.3d at

988, would have called for the testimony of Dennis Butler,

Wood’s client and Berkeley’s co-defendant in the 2000 drug

case. Because the ensuing conflict would have required Wood

to withdraw from representing Berkeley, and because Wood did

not want to lose the work, he avoided pursuing the entrapment

defense that would have led him down that path.

Berkeley’s conflict argument founders on its factual

premise -- that Berkeley advised Wood of Holden’s threat.

Without that predicate, Berkeley’s logical chain collapses: If

Wood did not know of the threat, he would have had no reason

to think that an entrapment defense was available. If he had no

reason to know such a defense was available, he would have had

no reason to know of the conflict that Berkeley claims would

have resulted from its assertion. And because an unknown

conflict could not have “adversely affected [Wood’s]

performance,” the Cuyler standard cannot be met. Cuyler, 446

U.S. at 348. 

Although Berkeley testified at the evidentiary hearing that

he informed Wood of Holden’s threatening letter, Mot. Hr’g Tr.

16, Wood testified to the contrary, id. at 123, 136, 143, 144, 146.

The district court resolved the dispute in favor of Wood’s

testimony, finding that Berkeley never informed Wood of this

predicate for an entrapment defense. Berkeley, 515 F. Supp. 2d

at 164. We review such a factual finding for clear error only,

United States v. Eli, 379 F.3d 1016, 1019 (D.C. Cir. 2004), and
10

3

The Homeland Security Act of 2002, Pub. L. No. 107-296, 116

Stat. 2135 (2002), abolished the Immigration and Naturalization

Service (INS) and transferred its enforcement responsibilities to the

Bureau of Immigration and Customs Enforcement (ICE). The

government explains, without contradiction, that “INS detainees” in

28 C.F.R. § 550.58 should now be read as “ICE detainees.” See

Appellee’s Br. 7 n.3; see also 28 C.F.R. § 550.55 (current version of

former § 550.58).

we find none. Because Wood’s performance could not have

been adversely affected by information he never possessed,

Berkeley’s conflict-of-interest argument must fail.

Berkeley’s second argument, that Wood misadvised him

regarding the possibility of early release, fares no better.

According to Berkeley, Wood advised him that he would be

eligible to receive up to a year of early release by participating

in a substance abuse treatment program under 28 C.F.R.

§ 550.58 (2008). Pursuant to that regulation, “INS detainees”

were ineligible for such early release, id. § 550.58(a)(i),3 and

Berkeley contends that he is certain to be subject to such a

detainer due to his immigration status.

Even if we assume for purposes of argument that Wood’s

advice was constitutionally infirm, Berkeley has not shown

prejudice under Strickland’s second prong. As we have

previously explained, “[w]here the defendant attacks a plea

bargain, the prejudice inquiry ‘focuses on whether counsel’s

constitutionally ineffective performance affected the outcome of

the plea process.’” Hanson, 339 F.3d at 990 (quoting Hill, 474

U.S. at 59). “‘[I]n order to satisfy the ‘prejudice’ requirement,

the defendant must show that there is a reasonable probability

that, but for counsel’s errors, he would not have pleaded guilty

and would have insisted on going to trial.’” Id. (quoting Hill,
11

474 U.S. at 59) (alteration in original). Berkeley cannot make

that showing.

Any competent attorney would have advised Berkeley that

he stood little chance of obtaining an acquittal if he went to trial

on the indictment filed against him in the District of Columbia,

and a good chance of receiving a higher sentence than if he pled

guilty. The video- and audio-tape evidence of his participation

in the two drug transactions was overwhelming, and -- as the

district court found -- Berkeley did not tell counsel that he had

a defense. Nor was there any reason to believe that Berkeley

would have had a successful defense to the gun and drug charges

that could have been filed against him in Maryland. There,

based on the crack found in his pocket alone, Berkeley faced a

mandatory minimum sentence of 5 years, 21 U.S.C. § 844(a),

and a Guidelines range of 78-97 months, see U.S.S.G.

§ 2D1.1(c)(7); U.S.S.G. ch. 5, pt. A (sentencing table). In return

for pleading guilty in D.C., the government agreed to ensure that

Berkeley would not face charges in Maryland. Plea Agreement

¶ 5. 

Berkeley “does not affirmatively allege, much less establish

to a reasonable probability, that he would have chosen to go to

trial” despite the risks, United States v. Scott, 64 Fed. Appx.

781, 782 (D.C. Cir. 2003), if only he had known that the advice

the court found Wood gave him -- that he “could be placed in a

Bureau of Prison[s] drug treatment program which, if completed

successfully, could allow him to be released from prison” up to

a year early -- was incorrect. Berkeley, 515 F. Supp. 2d at 165

(emphases added). Accordingly, Berkeley “cannot prevail on

his ineffective assistance of counsel claim.” Scott, 64 Fed.

Appx. at 782; see United States v. Horne, 987 F.2d 833, 835-36

(D.C. Cir. 1993) (holding that the defendant could not prove

prejudice from alleged ineffective assistance because he “has

never claimed that but for counsel’s errors he would have
12

pleaded not guilty and insisted upon going to trial”); see also

Curry, 494 F.3d at 1131; In re Sealed Case, 488 F.3d 1011,

1016 (D.C. Cir. 2007); Hanson, 339 F.3d at 991-92. 

III

In a pro se supplemental brief that we granted Berkeley

leave to file, he raises two further arguments, both challenges to

his sentence. Our review of sentencing decisions is limited. In

United States v. Booker, 543 U.S. 220 (2005), the Supreme

Court “invalidated both the statutory provision, 18 U.S.C.

§ 3553(b)(1) (2000 ed., Supp. IV), which made the Sentencing

Guidelines mandatory, and § 3742(e) (2000 ed. and Supp. IV),

which directed appellate courts to apply a de novo standard of

review to departures from the Guidelines.” Gall v. United

States, 128 S. Ct. 586, 594 (2007). As a consequence, “the

Guidelines are now advisory, and appellate review of sentencing

decisions is limited to determining whether they are

‘reasonable.’” Id.

We review the reasonableness of a sentence in two steps.

First, we must “ensure that the district court committed no

significant procedural error, such as . . . improperly calculating

. . . the Guidelines range [or] treating the Guidelines as

mandatory.” Id. at 597. Second, we “consider the substantive

reasonableness of the sentence imposed under an abuse-ofdiscretion standard.” Id. Berkeley’s challenges involve only the

accuracy of the district court’s Guidelines calculations. 

Berkeley’s primary contention is that the court erred in

refusing to decrease his offense level for acceptance of

responsibility. Because the “sentencing judge is in a unique

position to evaluate a defendant’s acceptance of responsibility[,]

. . . the determination of the sentencing judge is entitled to great

deference on review.” U.S.S.G. § 3E1.1 cmt. n.5.
13

The district court concluded that “[t]he motion to withdraw

a guilty plea in and of itself is a statement that Mr. Berkeley did

not wish to let the guilty plea stand, and therefore, he didn’t

wish to accept responsibility for this offense.” Sentencing Hr’g

Tr. 13-14. Berkeley insists that this was error because he

wished only to assert an entrapment defense and continued to

admit to “his guilt and involvement in the instant offense.”

Appellant’s Supp. Br. 4. Yet, by simultaneously claiming that

he accepted responsibility but that he was entrapped, Berkeley

was “in effect claiming that he accept[ed] responsibility even

though he was not responsible.” United States v. Kirkland, 104

F.3d 1403, 1405 (D.C. Cir. 1997). “It may be that a situation

could be presented in which an entrapment defense is not

logically inconsistent with a finding of a defendant’s acceptance

of responsibility,” but Berkeley did not automatically earn the

acceptance credit simply by claiming entrapment as his only

defense. Id. at 1406. Moreover, the district court “didn’t think

that Mr. Berkeley was telling the truth” about his alleged

entrapment defense, and the court made “very specific findings

about that.” Sentencing Hr’g Tr. 14. Under these

circumstances, the court was more than justified in denying an

offense-level reduction for acceptance of responsibility. Cf.

United States v. Mendoza, 42 Fed. Appx. 471, *1 (D.C. Cir.

2002) (“The district court did not clearly err in denying

appellant a downward adjustment for acceptance of

responsibility in light of the court’s determination . . . that

appellant untruthfully denied relevant conduct.”); United States

v. Taylor, 937 F.2d 676, 680 (D.C. Cir. 1991) (affirming a denial

of credit for acceptance of responsibility where the court found

that the defendant had not been “truthful and complete” in

explaining the circumstances of his crime).

Finally, we briefly address Berkeley’s further contention

that he was denied the benefit of a November 1, 2007 Guidelines

amendment aimed at ameliorating the disparity between crack
14

4

Berkeley argues in his supplemental reply brief that imposing an

obstruction-of-justice enhancement was an abuse of discretion.

Appellant’s Supp. Reply Br. 8. Arguments made in reply briefs,

particularly supplemental reply briefs, come too late for our

consideration. See Hwang Geum Joo v. Japan, 413 F.3d 45, 49 n.*

(D.C. Cir. 2005); United States v. Johnson, 216 F.3d 1162, 1168 (D.C.

Cir. 2000).

and powder cocaine sentences. See U.S.S.G. app. C, amend.

706. Prior to the amendment, an offense like Berkeley’s,

involving 50 to 150 grams of crack, would have resulted in a

base offense level of 32; following the amendment, it results in

a base offense level of 30. Compare U.S.S.G. § 2D1.1(c)(4)

(2006), with U.S.S.G. § 2D1.1(c)(5) (2007). Here, the district

court properly calculated Berkeley’s base offense level as 30,

pursuant to the amended Guidelines. The court calculated

Berkeley’s total offense level as 32, but this was based on a twolevel obstruction-of-justice enhancement that was unaffected by

the amendment. Sentencing Hr’g Tr. 6, 13-14. Hence, there

was no error in the court’s sentencing calculation.4

IV

Because the district court neither abused its discretion in

denying Berkeley’s motion to withdraw his guilty plea, nor

committed error in calculating Berkeley’s sentence, the court’s

judgment is 

Affirmed.