United States Court of Appeals

FOR THE DISTRICT OF COLUMBIA CIRCUIT

Argued November 19, 2020 Decided June 11, 2021

No. 19-3015

UNITED STATES OF AMERICA,

APPELLEE

v.

KENIEL AEON THOMAS, ALSO KNOWN AS DAVID MORGAN,

APPELLANT

Appeal from the United States District Court

for the District of Columbia

(No. 1:18-cr-00310-1)

Rosanna M. Taormina, Assistant Federal Public Defender, 

argued the cause for appellant. With her on the briefs was A.J. 

Kramer, Federal Public Defender. Tony Axam Jr., Assistant 

Federal Public Defender, entered an appearance.

Nicholas P. Coleman, Assistant U.S. Attorney, argued the 

cause for appellee. With him on the brief were Elizabeth 

Trosman and Kathryn L. Rakoczy, Assistant U.S. Attorneys.
2

Before: HENDERSON and GARLAND,

* Circuit Judges, and 

GINSBURG, Senior Circuit Judge.

Opinion for the Court filed by Senior Circuit Judge 

GINSBURG.

Concurring opinion filed by Circuit Judge HENDERSON

GINSBURG, Senior Circuit Judge: Keniel Thomas, a 

resident of Jamaica, pleaded guilty to one count of interstate

communication with intent to extort, in violation of 18 U.S.C. 

§ 875(b), after botching a lottery scam.

1 In the plea agreement, 

Thomas waived most of his rights to appeal. He retained only 

the rights to claim he received ineffective assistance of counsel 

and to appeal any upward departure from the sentencing 

guidelines range calculated by the district court. At sentencing, 

the district court did depart upward and sentenced Thomas to 

nearly six years’ imprisonment. 

Thomas mounts several challenges to his sentence. First, 

he argues the Government plainly breached the plea agreement 

at sentencing. We disagree. Second, he claims his waiver of 

rights to appeal is unenforceable and then raises four issues 

within the scope of the waiver. We assume without deciding 

the waiver was ineffective and reject these challenges on their 

merits. Third, Thomas argues the district court abused its 

* Then-Judge Garland was a member of the panel at the time this case 

was submitted but did not participate in the final disposition of the 

case. 

1 In a lottery scam, “scammers lead victims to believe they have won 

a drawing or lottery, but the cash or prizes will not be released 

without upfront payment of fees or taxes. Scammers frequently 

target the elderly.” U.S. Embassy in Jamaica, Lottery Scams, 

https://jm.usembassy.gov/u-s-citizen-services/victims-ofcrime/scams (last visited May 14, 2021).
3

discretion by departing upward from the guidelines range. We 

find no abuse of discretion. Finally, Thomas claims his 

attorney made mistakes at sentencing and during the plea 

bargaining process that deprived him of his right to the 

effective assistance of counsel under the Sixth Amendment to 

the Constitution of the United States. We remand some of 

Thomas’s ineffective assistance claims to the district court for 

further fact-finding and deny the rest. 

I. Background

We first discuss the plea agreement and the stipulated 

facts. After that, we summarize additional evidence the 

Government presented with its sentencing memorandum and 

the proceedings at the sentencing hearing.

A. The plea agreement 

As part of his plea agreement, Thomas stipulated to a 

statement of offense that established the following facts.

***

In June 2014, Thomas made a call to William Webster,

whom Thomas knew to be an elderly former judge. Thomas 

identified himself as the head of the Mega Millions lottery and 

told the Judge he was the winner of an eight-figure prize. To 

collect it, Webster needed only to make an advance payment of 

$50,000 to cover taxes. If Thomas thought Judge Webster 

would be easily fooled due to his advanced age, then he was 

seriously mistaken. Perhaps unbeknownst to Thomas, he was 

trying to scam a man who once headed the Federal Bureau of 

Investigation. After hanging up with Thomas, Judge Webster 

phoned the Bureau. 
4

The next day, Judge Webster called Thomas back, this 

time recording their conversation for the FBI. Thomas restated 

many of his falsehoods from the day before, except this time 

the fake prize amount quadrupled and the fake tax payment 

dropped to $20,000. Judge Webster humored Thomas, but did 

not agree to anything. Undeterred, Thomas made several more 

calls to Judge Webster over the following month. 

Eventually Thomas became frustrated and resorted to 

threats instead of false promises. On July 17, he called Judge 

Webster’s home phone and reached his wife, Lynda Webster. 

Thomas demanded the Websters pay him $6,000. If they did 

not pay him, then he would have both of them killed by a sniper 

and set fire to their home. To make his threats more plausible, 

Thomas recounted personal identifying information about the 

Judge, including his previous employment. He further told 

Mrs. Webster he had been surveilling her home. He correctly 

described the house and correctly stated no one had been home

the previous evening.

Thomas made more threats in additional conversations 

with Mrs. Webster over the following days. On July 21, in an 

especially shocking outburst, Thomas told her, “it is so easy 

killing you, you just a take a shot and put it in your sniper, aim, 

and the back of the head ... all you see is blood and marrow 

flying out.” He urged the Websters to pay him $6,000 in order 

to avoid this fate. 

Having no success in securing the $6,000, Thomas 

apparently gave up on the Websters. Three years later, federal 

agents arrested him entering the United States at a New York

airport.

***
5

In a deal with the Department of Justice, Thomas admitted 

to the facts above and pleaded guilty to one count of interstate 

communication with intent to extort, 18 U.S.C. § 875(b). In 

exchange, the Department agreed not to bring any additional 

charges.

In the plea agreement, the parties estimated his offense 

level under the Sentencing Guidelines at 20, comprising a base 

offense level of 18, U.S.S.G. § 2B3.2; a two-level increase 

because his extortionate conduct included death threats, 

U.S.S.G. § 2B3.2(b)(1); a one-level increase because he tried 

to extort more than $20,000, U.S.S.G. § 2B3.2(b)(2); a twolevel increase for conduct aimed a vulnerable victim, U.S.S.G. 

§ 3A1.1; and a three-level decrease for acceptance of 

responsibility, U.S.S.G. § 3E1.1. Thomas had no prior 

criminal convictions, so this offense level resulted in an 

estimated guidelines range of 33 to 41 months in prison. See

U.S.S.G. § 5A. In the agreement, Thomas waived his right to 

appeal “except to the extent” the court sentenced him “above 

the statutory maximum or the guidelines range determined by 

the Court” but he reserved the right to claim he received 

ineffective assistance of counsel. 

B. Sentencing 

After Thomas pleaded guilty, the Government submitted a 

sentencing memorandum accompanied by 38 exhibits, which 

gave a fuller picture of the FBI’s investigation than had the 

statement of offense. The evidence suggested a long-running

and intricate conspiracy. According to the sentencing 

memorandum, it was not Thomas but his associate “Stone” 

who first contacted Judge Webster. In March 2014, Stone 

called Judge Webster, informed him he had won the lottery, 

and instructed him to send $1,000 to a California man 
6

identified in the record as “P.W.” Judge Webster immediately 

contacted the FBI. 

At the Bureau’s request, Judge Webster stayed in phone 

and email contact with Stone, and his associates “Dudley,” 

“Reinhardt,” “Davis,” and “Winslow” over the next few 

months. The FBI’s investigation revealed P.W. was a victim 

who had been tricked into serving as a “money mule” for 

Thomas and his associates. The FBI identified dozens of other 

victims in the United States, many of them elderly. Agents 

were able to trace over $300,000 of payments flowing to 

Thomas and his associates, but estimated the total loss was 

much higher. For instance, one eighty-two year old victim

claimed to have lost over $600,000, although the FBI was able 

to trace less than one-third of his loss. 

Thomas did not dispute any of these facts in his sentencing 

memorandum. At the sentencing hearing, however, Thomas’s 

attorney objected to a paragraph in the presentence 

investigation report (PSR) prepared by the Probation Office

that mentioned there were victims besides the Websters. The 

district judge overruled the objection after an FBI agent 

testified to the findings of the investigation. The agent’s 

testimony corroborated the evidence in the Government’s 

sentencing memorandum (and thus the disputed paragraph of 

the PSR). The court accepted the unrebutted evidence 

presented in the sentencing exhibits and the agent’s testimony 

as its findings of fact. 

The district court went on to impose a sentence longer than 

the Government had requested. The court applied an offenselevel enhancement not mentioned in the plea agreement 

because it found Thomas “demonstrated the ability to carry 

out” his threats. See U.S.S.G. § 2B3.2(b)(3)(B)(ii). This 

brought the sentencing guidelines range up to 46-57 months. 
7

The court then applied two upward departures suggested in the 

Extortion Guideline: one for extortion that “involved organized 

criminal activity” and one for “a threat to a family member of 

the victim.” U.S.S.G. § 2B3.2 cmt. n.8. As a result, the court 

sentenced Thomas to 71 months in prison, 30 months more 

than the maximum estimated in the agreement. 

II. Analysis

We begin our analysis with the alleged breach of the plea 

agreement. Second, we analyze the waiver of appellate rights 

in the plea agreement and the issues that it arguably bars. 

Third, we review the district court’s decision to depart from the 

guidelines range. In the final section, we address Thomas’s 

ineffective assistance of counsel claims. 

A. Breach of plea agreement

In the plea agreement, the Government promised it would 

not “seek any offense-level calculation different” from the 

calculation in the agreement. ECF No. 20, at 4. On appeal, 

Thomas argues the Government breached the plea agreement 

by seeking a sentencing enhancement for a demonstrated 

ability to carry out an extortionate threat.

Because Thomas did not object at sentencing, our review 

is for plain error. Puckett v. United States, 556 U.S. 129, 133-

34 (2009). We may reverse only if any breach (1) was “clear 

or obvious, rather than subject to reasonable dispute,” 

(2) prejudiced the defendant, and (3) resulted in a miscarriage 

of justice. Id. at 135. We find no breach here regardless of the 

standard of review. 

The Government did not mention the demonstrated-ability 

enhancement in its sentencing memorandum. At the 
8

sentencing hearing, the judge on her own initiative asked the 

prosecutor about it. The prosecutor, noting he was in an 

“unfortunate and somewhat difficult position,” stated it “was 

our interpretation and our understanding of the facts that we 

have before us that this offense did not involve the ability of 

the defendant to carry out this threat given what we knew at the 

time.” The judge pushed back, asking “in this case don’t we 

have the defendant talking to Lynda Webster and ... trying to 

demonstrate with pretty concrete evidence his ability to carry 

out his threat?” But the prosecutor stood his ground: “Our 

position is that he was not able to otherwise demonstrate the 

ability to carry that out through those threats.” The judge asked 

whether the Government’s position was contrary to her reading

of cases from the Third and Seventh Circuits, which held it is 

“irrelevant” whether the defendant “actually had the ability to 

carry it out.” The prosecutor said, no, “we’re basing it in large 

part on the facts ... in our case.” The court asked whether 

actual ability was irrelevant “as a legal matter” – trying to 

understand whether the Government took that position 

“because he was in Jamaica, we didn’t think he had the ability 

to carry it out; you don’t think it applies.” The prosecutor said 

no, “as a legal matter, we are not saying that.” After taking a 

moment to confer with a colleague, he concluded: “We are not 

arguing that legally that it doesn’t apply. We are not asking 

that it apply in this case.” 

There was no breach here. The Government promised to 

argue for the stipulated guidelines range (which it did), but it 

never promised to convince the judge this range was correctly 

calculated. See Plea Agreement, ECF 20, at 5 (“[Thomas]

acknowledges that the Court is not obligated to follow any 

recommendation of the Government at the time of 

sentencing”). 
9

Thomas interprets the double negative in the prosecutor’s 

penultimate sentence, “We are not arguing that legally that it 

doesn’t apply,” as “effectively agree[ing]” the court should 

apply the demonstrated-ability enhancement, and argues this 

constitutes a breach. We read the transcript differently. The 

prosecutor resisted the court’s characterization of the 

Government’s position, namely, that the enhancement is 

appropriate only where the defendant had the power to carry 

out his threats, so Thomas’s being in Jamaica (and presumably 

unable to harm the Websters) was dispositive. Rather, the 

prosecutor seemed to agree with the court’s view of the law but

maintain that the totality of the facts did not support the 

enhancement. 

This is how the Government reads the transcript as well. 

As it points out, nothing in the plea agreement required the 

prosecutor to argue for a bright-line rule that a defendant’s 

inability to make good on his threats is dispositive; to the 

contrary, he had an ethical duty to answer the court’s questions

honestly. 

Even if we understood the double negative as a feeble 

admission the enhancement might apply, we would still hold 

the prosecution did not breach the agreement. The fact is that, 

as agreed, the Government did not at any point “seek” the 

enhancement. The district court raised it without any 

prompting – explicit or implicit – from the Government and 

applied it over the Government’s repeated objection.

B. Waiver of rights to appeal

In exchange for “concessions made by the Government” 

in the plea agreement, Thomas waived his right to “appeal the 

sentence in this case ... and the manner in which the sentence 

was determined, except to the extent the Court sentence[d] 
10

[him] above the statutory maximum or guidelines range 

determined by the court.” A waiver of the right to appeal is 

“generally enforceable,” so long as it is “knowing, intelligent, 

and voluntary.” United States v. Guillen, 561 F.3d 527, 528-

29 (D.C. Cir. 2009) (analyzing a similar waiver). Thomas 

raises several issues that fall within the scope of the waiver.2 

He attempts to bypass the waiver in two ways. 

First, Thomas argues that because the district court 

departed upward from the guidelines range he is free to 

challenge his sentence upon any ground whatsoever. This is 

belied by the text of the agreement, which barred an appeal 

“except to the extent” the court sentenced him above the 

guidelines range. See United States v. Hunt, 843 F.3d 1022, 

1027 (D.C. Cir. 2016) (“Like statutory construction, 

interpretation of a plea agreement begins with plain language” 

(citations omitted)). The extent to which the court sentenced

Thomas above the guidelines range is the portion of the 

sentence attributable to the upward departure. Cf. Cohen v. de 

la Cruz, 523 U.S. 213, 218 (1998) (interpreting “to the extent 

obtained by” fraud to mean “the share ... that is obtained by 

fraud”). To challenge the underlying guidelines calculation or 

other aspects of the sentencing would be to go beyond the 

extent of the upward departure. 

Second, Thomas argues the district court’s explanation of 

the waiver of rights to appeal at his plea hearing effectively 

2 Specifically, he asserts the district court abused its discretion and/or 

clearly erred by (1) finding an incorrect “amount demanded” under 

the Extortion Guideline, (2) applying the “vulnerable victim” 

enhancement under U.S.S.G. § 3A1.1(b)(1), (3) applying the 

demonstrated-ability enhancement, (4) describing the lottery scam as 

an “extortion scheme” rather than a scheme to defraud, and (5) 

failing to provide a reasonable basis for rejecting a downward 

variance based upon his status as a deportable alien.
11

altered the terms of the waiver to allow appeal on any issue in 

the event of an upward departure. This contention cannot be 

rejected as easily as the previous one.

Before a district court may accept a guilty plea, Rule 11(b) 

of the Federal Rules of Criminal Procedure requires the judge 

to “inform the defendant of, and determine that the defendant 

understands,” certain important terms and consequences of the 

plea agreement. The purpose of the Rule, generally, is “to 

ensure that [the defendant] understands ... his rights as a

criminal defendant” before entering a guilty plea. United 

States v. Vonn, 535 U.S. 55, 62 (2002). A waiver of rights to 

appeal is a consequential term in a plea agreement, so the Rule 

specifically requires the judge to explain its terms to the 

defendant and to confirm the waiver is entered knowingly, 

intelligently, and voluntarily. Fed. R. Crim. P. 11(b)(1)(N); see 

also United States v. Lee, 888 F.3d 503, 506 (D.C. Cir. 2018). 

Due to the vital constitutional interests Rule 11 safeguards, 

we have insisted that district courts “scrupulously adhere” to 

its requirements. United States v. Brown, 892 F.3d 385, 395 

(D.C. Cir. 2018) (quoting United States v. Shemirani, 802 F.3d 

1, 3 (D.C. Cir. 2015)). If “the district court mischaracterize[s] 

the meaning of the waiver in a fundamental way” at the plea 

hearing, then “the district court’s oral pronouncement controls, 

and the appeal is not barred.” Brown, 892 F.3d at 395 (quoting 

United States v. Godoy, 706 F.3d 493, 495-96 (D.C. Cir. 2013), 

cleaned up); see also, e.g., Hunt, 843 F.3d at 1028-29; United 

States v. Kaufman, 791 F.3d 86, 88 (D.C. Cir. 2016). A 

representative case is Brown, where the district court 

summarized a waiver provision nearly identical to the one here 

as follows: “[W]ith regard to certain circumstances, you may 

even have ... the right to appeal the sentence ... on the grounds 

of reasonableness.” 892 F.3d at 395. On appeal, we did not 

“pause to parse the precise legal meaning of ‘reasonableness.’” 
12

Id. at 396. Instead, we refused to enforce the waiver based 

upon “the common meaning” of the district court’s 

pronouncement. Id. 

Scrupulous implementation of Rule 11 does not require “a 

litany or other ritual which can be carried out only by wordfor-word adherence to a set ‘script.’” Fed. R. Crim. P. 11(h), 

Advisory Committee’s Notes to 1983 Amendment. To the 

contrary, a lifeless recitation of the plea agreement is 

disfavored; “a more meaningful explanation” in the judge’s 

own words is preferred. Id. (quoting United States v. Saft, 558 

F.2d 1073, 1079 (2d Cir. 1977)). It is, admittedly, a delicate 

balance the district court must strike: Provide enough 

explanation to dispel any misunderstanding without simply 

reading the agreement aloud, but in doing so, take care not to

create a new or different misconception that effectively amends

the written agreement. 

During the Rule 11 colloquy in this case, the court

explained the waiver as follows:

THE COURT: Do you understand that by pleading guilty 

you are giving up all of your rights ... to appeal your 

sentence, unless you are sentenced to a period of 

imprisonment longer than the statutory maximum or the 

court departs upward from the applicable recommended 

sentencing guideline range, which is all set out in your plea 

letter at page 7, paragraph 10? Do you understand that?

THE DEFENDANT: Yes, Your Honor.

The key difference between the written agreement and the 

court’s explanation is that the court paraphrased “except to the 

extent” as “unless.” Thomas says there is an “arguable
13

divergence” between the court’s explanation and the agreement 

as written, and so the court’s explanation should control. 

We agree the two arguably diverge insofar as “unless” is 

less precise and broader than “except to the extent.” The 

written terms of the agreement, as explained above, were 

specific.

3

 The district court’s paraphrase, taken literally, tells 

the defendant he is not giving up all his rights to appeal if the 

district court departs upward, but does not specify which rights 

would be retained if that happened. The natural understanding, 

however, is that the right retained is the right mentioned – that 

is, the right to appeal the upward departure. As the 

Government put the point at oral argument, “There’s no reason 

why the decision to ... go above the guidelines range should 

then make everything else appealable. That isn’t ... a 

reasonable interpretation of the provision.”

In light of these conflicting considerations, I think that 

whether the district court fundamentally mischaracterized the 

waiver provision is a close question. But see Henderson, J., 

Concurring Op., post. We need not answer it, however, because 

Thomas’s challenges to the arguably waived issues lack merit. 

See United States v. Fry, 851 F.3d 1329, 1331-32 (D.C. Cir. 

2017) (“Because the waiver question does not go to our court’s 

jurisdiction, we can forgo deciding it if we reject [defendant’s] 

sentencing challenges on the merits”).

3 This is not to say the written waiver was beyond improvement. The 

written waiver in Brown, for example, was even more specific; it 

stated the defendant could appeal an above-guidelines sentence but 

could not “raise on appeal other issues regarding the sentencing.” 

892 F.3d at 395. 
14

1. Stipulated guidelines enhancements

Thomas faults the district court for applying two offense 

level enhancements recommended in the plea agreement, to 

wit, the vulnerable victim enhancement, U.S.S.G. 

§ 3A1.1(b)(1), and the enhancement for extortion where the 

amount demanded exceeded $20,000, U.S.S.G. § 2B3.2(b)(2). 

The Government argues he waived his right to challenge this 

aspect of the guidelines calculation, quite apart from the

explicit waiver of his right to appeal, by negotiating and 

accepting a plea deal that stipulated the enhancements apply. 

Therefore, the Government argues, we should not review this 

aspect of the guidelines calculation even for plain error. 

The Government is correct. While we review for plain 

error when a defendant has forfeited an issue through a failure 

to object, we will not review at all when a defendant acts 

intentionally to waive an issue. United States v. Laslie, 716 

F.3d 612, 614 (D.C. Cir. 2013) (citing United States v. Olano, 

507 U.S. 725, 733 (1993) for the distinction between forfeiture 

and waiver). For instance, when a defendant makes a “tactical 

decision” to request a certain jury instruction, he is barred from 

complaining about the instruction on appeal; any error was 

“invited” by the defendant. United States v. Harrison, 103 F.3d 

986, 992 (D.C. Cir. 1997); Brown, 892 F.3d at 392-93; cf.

United States v. Long, ___ F.3d ___, No. 20-3064, 2021 WL 

1972245, at *6-7 (D.C. Cir. May 18, 2021) (no waiver where 

counsel made a “mistake” rather than employing a “strategy or 

tactic”). This rule discourages sandbagging, that is,

purposefully inducing the district court to commit an error that 

can form the basis for an appeal in the event of an unfavorable 

result at trial or sentencing. Harrison, 103 F.3d at 992. 

Negotiating a plea agreement, like requesting a jury 

instruction, requires counsel to think strategically. See Guillen, 
15

561 F.3d at 530. In both situations counsel must evaluate the 

various options and advise the defendant of their respective

risks and benefits. And in both situations there is a potential 

for sandbagging. Therefore, we have held a defendant waives 

his right to contest a guidelines adjustment to which he has 

stipulated in his plea agreement: “This court does not allow 

parties to reopen issues waived by stipulation at trial.” Laslie, 

716 F.3d at 615.

We have no doubt that Thomas intentionally waived the 

issues he now seeks to raise; there was no mere forfeiture or 

mistake. Thomas’s plea agreement provided for an offense 

level increase because the “amount demanded” exceeded

$20,000, U.S.S.G. § 2B3.2(b)(2), and another increase because

“a victim of the offense was a vulnerable victim,” U.S.S.G. 

§ 3A1.1(b)(1). At the Rule 11 hearing, the judge asked Thomas 

whether he understood the estimate in the plea agreement that 

his offense level would be increased “by one offense level 

because you demanded over $20,000[] and by two offense 

levels because the two victims were vulnerable victims.” 

Thomas confirmed that he understood. When the Probation 

Office produced the PSR, it confirmed the parties’ guidelines 

calculation. In his sentencing memorandum Thomas adverted 

to this portion of the PSR but did not object to it. Finally, when 

at the sentencing hearing the court accepted the 

recommendation to apply these two enhancements, Thomas, 

through counsel, again stated he did not object. 

Despite all this, Thomas argues there was no waiver 

because the district court stated it had an “independent 

obligation” to calculate the guidelines range rather than relying 

solely upon the calculation estimated by the parties. Therefore, 

he says, his stipulation did not induce the district court’s 

decision and we should review for plain error after all. The 

point is not well taken; the district court has an “independent 
16

obligation” to calculate the guidelines range in every case. 

Freeman v. United States, 564 U.S. 522, 529 (2011). If that 

undercut the defendant’s waiver here, it would do so 

everywhere. Therefore, we hold Thomas waived his challenge 

to the two disputed enhancements. 

2. Demonstrated ability

The Extortion by ... Threat of Injury Guideline provides 

for an enhancement of three offense levels if “the offense 

involved preparation to carry out” or the defendant “otherwise 

demonstrated the ability to carry out” a threat of death, serious 

injury, or kidnapping. U.S.S.G. § 2B3.2(b)(3)(B). Application 

Note 6 explains the enhancement would be appropriate if, for 

example, “an extortionate demand containing ... a threat to 

kidnap a person [were] accompanied by information showing 

study of that person’s routine.” The district court applied this 

enhancement over the objection of both Thomas and the 

Government.

The district court did not abuse its discretion by applying 

the enhancement on these facts, which closely track the 

example from Note 6. Indeed, the Seventh Circuit upheld 

application of the enhancement to similar facts in United States 

v. Hacha, 727 F.3d 815 (2013). There the extortionist, who

threatened to harm the victim’s parents, demonstrated his 

ability to carry out the threat by telling the victim (1) his 

parents’ names, (2) their address in Mexico City, and (3) the 

color of their house. Id. at 817. Here, Thomas showed the 

Websters he knew their names, home address, and house color, 

and went farther still. To corroborate his claim the house was 

under surveillance, he correctly told Mrs. Webster she was not 

home the night before. 
17

Thomas argues he did not demonstrate an ability to carry 

out his threats because he did not actually have the ability to 

carry them out; he was, after all, in Jamaica at the time. But 

the defendant being out of the country is not dispositive

because having and demonstrating an ability are not the same 

thing. See United State v. White, 654 F. App’x 956, 969-70 

(11th Cir. 2016) (holding the defendant, who was in Mexico at 

the time, demonstrated the ability to carry out threats against 

Florida officials when he revealed he knew their names, 

addresses, and grandchildren’s names).

3. “Extortion scheme” or “scheme to defraud”

Thomas claims the court erred by referring several times 

at sentencing to an “extortion scheme.” According to Thomas, 

the scheme is more accurately characterized as a “scheme to 

defraud” because most calls to victims did not include 

extortionate threats. Thomas never objected to the court’s 

characterization at sentencing, so our review is for plain error. 

Even granting that the court’s use of the phrase was inaccurate, 

the challenge fails because Thomas does not explain how it 

affected his substantial rights. 

4. Smith variance

As a deportable alien, Thomas is not eligible for “the 

benefits of 18 U.S.C. § 3624(c), which directs the Bureau of 

Prisons, to the extent practicable, to assure that prisoners spend 

part of ... their sentences ... under conditions — possibly 

including home confinement — that will ‘afford the prisoner a 

reasonable opportunity to adjust to and prepare for his re-entry 

into the community.’” United States v. Smith, 27 F.3d 649, 651 

(D.C. Cir. 1994). In his PSR, the Probation Office raised the 

possibility of a downward departure to compensate for the 

increased severity of Thomas’s punishment due to his 
18

ineligibility for this and other Bureau of Prisons programs (a 

Smith departure). See id. at 655. At the sentencing hearing, 

defense counsel declined to argue in support of this departure 

because he was bound by the plea agreement not to argue for 

any departures, but he said he intended to argue later for a 

downward variance on those same grounds (a Smith variance). 

At the appropriate time, however, defense counsel did not raise 

Smith or otherwise make the case for a variance. Later in the 

hearing, the district judge independently considered granting a 

variance or departure under Smith. She concluded neither was 

warranted: “[G]iven the fact that you committed your current 

offense while you were in Jamaica, it appears to me that being 

abroad doesn’t impede your criminal conduct here; I’d only 

delay bringing you to justice here.” 

Thomas argues the district court did not articulate a 

reasoned basis for declining to impose a departure or a variance 

under Smith. See Rita v. United States, 551 U.S. 338, 356 

(2007) (“The sentencing judge should set forth enough to 

satisfy the appellate court that he has considered the parties' 

arguments and has a reasoned basis for exercising his own legal 

decisionmaking authority”). Because Thomas did not object to 

the district court’s statement of reasons at sentencing, our 

review would be for plain error if we were to reach this 

argument. United States v. Locke, 664 F.3d 353, 357 (D.C. Cir. 

2011). For reasons stated later in this opinion, however, we 

hold Thomas’s attorney was ineffective as a matter of law in 

failing to argue for and present evidence supporting a Smith

variance and in failing to object to the district court’s stated 

reason for denying one. This ineffective assistance of counsel 

claim will be remanded to the district court so it can determine 

whether counsel’s errors were prejudicial. On remand, the 

district court will need to consider arguments for the variance 

and will have to provide a reasoned basis for accepting or 

rejecting them. Consequently, we need not decide whether the 
19

district court plainly erred. Cf. United States v. Soto, 132 F.3d 

56, 59 (D.C. Cir. 1997) (“In view of our conclusion that 

counsel was ineffective, we need not reach [the defendant’s] 

alternative argument that the district court committed plain 

error”).

C. Upward departures

In Application Note 8 to the Extortion Guideline, the 

Sentencing Commission advises that “[i]f the offense involved 

organized criminal activity, or a threat to a family member of 

the victim, an upward departure may be warranted.” U.S.S.G. 

§ 2B3.2 cmt. n.8. The district court found Thomas’s offense 

involved both organized criminal activity and a threat to a 

family member and departed upward upon both grounds. 

Thomas attacks the rationales for both departures. He first 

argues the district court erred by treating Application Note 8 as 

a “directive” rather than a suggestion. As the transcript shows, 

however, the district court well understood the departures to be 

permissive: “So I am going to address the two departures ...

that are expressly recommended for consideration where the 

facts warrant.”

The district court was clearly correct the conduct involved 

threats to a family member. Thomas told Mrs. Webster several 

times he would murder her husband if he was not paid. These 

threats were recorded and Thomas admits to making them. 

Thomas insists “a threat to a family member of the victim” 

means a threat communicated to that family member. Under 

this interpretation, the departure would be justified only in rare 

circumstances, if ever, because the person with whom the 

extortionist speaks will usually be “the victim” of the extortion, 

not a relative of the victim. Thomas’s reading of the Guideline
20

is strained and unnatural: If a victim said an extortionist called 

and threatened to kill his toddler, one would not understand the 

victim to have put the child on the phone. The better 

interpretation is that the departure is permitted where the 

defendant threatens the victim with harm to a member of the 

victim’s family. 

Regarding the organized crime departure, Thomas asks us 

to view the phone calls to Mrs. Webster in isolation. Because 

none of Thomas’s associates joined him on the calls, he reasons 

the offense did not involve organized crime. The district court 

was not required to take such a narrow view. The extortionate 

threats were made as the culmination of a plot that involved 

Thomas and other members of his criminal organization. 

Thomas’s associates also contacted the Websters, and Thomas 

directed the Websters to send money to his mules as part of a 

complex, orchestrated scheme. Even looking only to the 

recording of the July 21 phone call, there is evidence of 

organized crime. Thomas spoke in the first-person plural (e.g., 

“We know where your home is. We have your address. We 

have everything about you. So easy that we go set your home 

ablaze.”) and directed Mrs. Webster to send money to his 

“good friend” in New York. 

Finally, Thomas attacks the extent of the organized-crime 

departure. He argues the district court abused its discretion by 

adding one offense level to account for the scope of the 

organization’s crimes because, in doing so, the court 

analogized to the loss table in the Robbery Guideline, U.S.S.G. 

§ 2B3.1(b)(7). He says the court should have looked instead to 

the Fraud Guideline, U.S.S.G. § 2B1.1. But the loss table in 

the Fraud Guideline escalates much more quickly: it prescribes 

an increase of eight levels if the loss exceeded $95,000 and an 

increase of 12 levels if the loss exceeded $250,000. Therefore, 
21

Thomas benefitted from the analogy and has neither standing 

nor reason to complain about it. 

D. Ineffective assistance

Thomas claims his defense attorney made several errors 

during plea negotiations and at sentencing that deprived him of 

his Sixth Amendment right to counsel. To prevail on these 

claims, Thomas must show (1) his attorney made errors so 

serious he was not functioning as “counsel,” and (2) the errors 

were prejudicial. United States v. Rashad, 331 F.3d 908, 909 

(D.C. Cir. 2003). When a defendant asserts ineffective 

assistance claims for the first time on direct appeal, we 

“remand the claim for an evidentiary hearing unless the trial 

record alone conclusively shows that the defendant either is or 

is not entitled to relief.” Id. at 909-10 (cleaned up). 

The Government agrees that several of the ineffective 

assistance claims should be remanded to the district court for 

fact-finding.4

 It argues, however, that four of the claims should 

be dismissed in this appeal, viz., that defense counsel: (1) failed 

to argue for or present facts supporting a Smith variance, and 

failed to object to the district court’s reason for rejecting one;5

(2) “affirmatively agreed” to “incorrect” offense-level 

enhancements; (3) failed to argue persuasively against the 

“demonstrated ability” enhancement; (4) did not object to the 

4 The Government does not object to remanding the ineffective 

assistance claims based upon defense counsel’s failure: (1) to present 

“documentation” supporting a Smith variance, (2) raise mitigating 

facts contained in the Government’s sentencing exhibits, (3) review 

the exhibits with Thomas, and (4) submit character letters Thomas’s 

family and friends had written. We remand these claims to the 

district court for further proceedings. 

5 The Government agrees this claim must be remanded in part. See 

supra, n.4. As discussed below, we remand it in full. 
22

Government’s breach of the plea agreement; and (5) presented 

no argument against the “organized criminal activity” and 

“threat to family member” departures. We will address these 

individually. 

1. Smith variance

The record conclusively shows Thomas’s counsel made 

unprofessional errors in failing to seek a downward variance 

due to Thomas’s status as a deportable alien. Even before the 

Supreme Court’s decision in United States v. Booker allowed 

judges to vary from the Sentencing Guidelines, 543 U.S. 220 

(2005), this Circuit recognized “a downward departure may be 

appropriate where the defendant’s status as a deportable alien 

is likely to cause a fortuitous increase in the severity of his 

sentence.” Smith, 27 F.3d at 655. In Thomas’s PSR, the 

Probation Office noted his “status as a deportable alien may 

warrant a downward departure.” 

Defense counsel did not zealously or diligently pursue a 

Smith variance.6

 In Thomas’s sentencing memorandum, 

counsel did not even echo the Probation Office’s call for a 

sentencing reduction or otherwise bring up Smith. Defense 

counsel later submitted a supplemental sentencing 

memorandum requesting a downward variance based upon 

Thomas’s susceptibility to “physical beating” in jail, which 

Thomas attributed to his nationality. The supplemental 

memorandum again failed to mention Smith or the Probation 

Office’s suggestion. Then, at sentencing, the court asked the 

6 The plea agreement prohibited defense counsel from seeking a 

downward departure, so counsel would have needed to request a 

Smith variance rather than a Smith departure. This difference is 

immaterial here because, as defense counsel recognized, the 

considerations animating Smith apply equally to a variance and a 

departure. 
23

parties to comment on the possibility of a Smith departure. 

Defense counsel, being unable to seek a downward departure, 

could not opine but stated he would raise Smith again when the 

court considered variances. When the time came, however, 

defense counsel did not raise Smith, choosing instead to rest on 

the arguments in his original sentencing memorandum.

7

The court returned to the issue on its own later in the

hearing, stating: 

I have also considered whether or not there should be a 

downward variance or departure due to your deportation 

after this sentence and the fact that there might be an 

increase in the severity of your sentence because of your 

inability to serve the last part of your sentence in a 

community-based confinement or in some kind of reentry 

program. But given the fact that you committed your 

current offense while you were in Jamaica, it appears to 

me that being abroad doesn't impede your criminal 

conduct here; I'd only delay bringing you to justice here. 

Defense counsel did not object to this explanation. 

It is clear from the record that defense counsel acted 

unprofessionally in failing to seek a Smith variance after the 

issue was flagged in the PSR. Cf. Soto, 132 F.3d at 58-59 

(holding counsel was clearly ineffective where he failed to 

raise a “potentially helpful” provision of the Guidelines). The 

7 Specifically, when the time came to discuss variances, the judge 

listed the five variances defense counsel requested in the sentencing 

memorandum (which did not include a variance under Smith), and 

asked him “Is that basically it?” Counsel responded, “Yes, Your 

Honor, that is effectively it.” The judge asked whether counsel had 

anything to add to his variance arguments, but counsel stated: “There 

is nothing more to amplify.”
24

record shows this was not a strategic choice; counsel stated his 

intent to raise the issue, but then failed to do so. This was an 

error serious enough, if it affected the outcome, to deprive 

Thomas of his constitutional right to counsel. 

What is less clear is whether Thomas suffered any 

prejudice. Despite counsel’s failure to request the variance, the 

district court considered whether to grant it. The district court 

may or may not have been persuaded had counsel offered a 

cogent argument. We remand this claim to the district court to 

allow Thomas to present arguments and evidence supporting a 

Smith variance.

2. Stipulated guidelines enhancements

In his plea agreement, Thomas stipulated to two 

enhancements of his offense level that he now argues were 

inappropriate: (1) a one-level increase because “the amount 

demanded ... exceeded $20,000,” U.S.S.G. § 2B3.2(b)(2), and 

(2) a two-level increase because Thomas “knew or should have 

known that a victim of the offense was a vulnerable victim,” 

U.S.S.G. § 3A1.1(b)(1). 

To determine whether these enhancements apply, a court 

may consider only the “relevant conduct” as defined in the 

Guidelines, which includes acts and omissions “that occurred 

during the commission of the offense of conviction, in 

preparation for that offense, or in the course of attempting to 

avoid detection or responsibility for that offense.” U.S.S.G. 

§ 1B1.3(a). Whether the two enhancements were appropriate 

would depend in large part upon whether the relevant conduct 

included the calls to Mrs. Webster only or included also the 

calls to Judge Webster: Thomas demanded $50,000 during his 

attempt to defraud Judge Webster, but demanded only $6,000 

from Mrs. Webster; Judge Webster was arguably a vulnerable 
25

victim because he was over 90 years old at the time of the 

offense, but there is no suggestion Mrs. Webster was unusually 

vulnerable. The Government asserted in the district court that 

the relevant conduct included the calls to both Websters, but it

does not defend that position on appeal; nor does it otherwise 

argue the enhancements were correctly applied. 

Even if the enhancements were erroneous, however, 

Thomas’s objections fail because he cannot make a plausible 

showing of prejudice. Thomas principally argues that, if his 

counsel had informed him that the relevant conduct did not 

support some of the enhancements recommended in the 

agreement, then he would have negotiated a more lenient 

agreement. To prevail on this claim, Thomas would have to 

“show a reasonable probability that the end result of the 

criminal process would have been more favorable by reason of 

a plea to a lesser charge or a sentence of less prison time.” 

Brock-Miller v. United States, 887 F.3d 298, 312 (7th Cir. 

2018) (quoting Missouri v. Frye, 566 U.S. 134, 147 (2012))

(applying this standard of prejudice to a claim that but-for 

counsel’s errors, the defendant would have “negotiated a more 

favorable plea agreement”). 

Thomas cannot make that showing. Given the uncharged 

conduct in the stipulated facts and the extra-plea evidence, it is 

completely unreasonable to believe the Government would 

have offered Thomas a more lenient deal if counsel had 

objected to the enhancements. Even if he convinced 

prosecutors they had erred, they surely would have added 

counts sufficient to maintain at least the same recommended 

guidelines range. Indeed, the prosecution stressed to the 

district court that the sentence should reflect the “harm the 

defendant inflicted on numerous vulnerable victims,” including 

losses of “at least $300,000” and “likely much higher.” ECF 

No. 28 at 10, 13. 
26

Alternatively, Thomas argues “it is not unlikely that he 

would have chosen either to enter an open plea or to proceed to 

trial, but for counsel’s errors.” For the open plea claim, he must 

show he would have obtained a more favorable sentence but

for counsel’s errors. See Garcia v. United States, 679 F.3d 

1013, 1015 (8th Cir. 2012); United States v. Booth, 432 F.3d 

542, 546-47 (3d Cir. 2005). The claim he would have 

proceeded to trial is governed by the standard announced in Lee 

v. United States, 137 S. Ct. 1958, 1965 (2017) (“[W]hen a 

defendant claims that his counsel’s deficient performance 

deprived him of a trial by causing him to accept a plea, the 

defendant can show prejudice by demonstrating a reasonable 

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

pleaded guilty and would have insisted on going to trial.” 

(cleaned up)). 

Thomas cannot satisfy either standard. Again, the

Government had evidence of uncharged conduct that would 

have supported numerous fraud counts on top of the lone 

extortion count in the information. It is highly improbable that 

Thomas would choose to proceed without a plea deal simply 

because defense counsel pointed out some logical 

inconsistencies in the Government’s offer. 

Because Thomas cannot show prejudice on these claims, 

we shall not remand them to the district court. 

3. Demonstrated ability

Thomas’s next ineffective assistance claim is that defense 

counsel “failed to effectively argue” that the court should not 

apply the demonstrated-ability enhancement of U.S.S.G. 

§ 2B3.2(b)(3)(B)(ii). This claim must fail because the district 

court was bound to apply the enhancement for reasons already 
27

stated. Cf. United States v. Winstead, 890 F.3d 1082, 1090 

(D.C. Cir. 2018) (examining whether the argument counsel 

failed to raise was a “winning argument” in order to determine 

whether raising it would have changed the result). 

4. Breach of plea agreement

Thomas claims defense counsel’s performance was 

constitutionally deficient because he failed to object to the 

Government’s breach of the plea agreement. As already 

discussed, however, the Government did not breach the plea 

agreement. We reject this claim because “failure to raise a 

meritless objection is not deficient performance.” United 

States v. Islam, 932 F.3d 957, 964 (D.C. Cir. 2019). 

5. Upward departures

Finally, Thomas claims defense counsel “presented no 

substantive argument against” the two upward departures. This 

is true. Nevertheless, as we explained, the departures were 

justified. There is no reason to believe an argument against 

them could have affected the outcome. We shall not remand 

this claim. 
28

III. Conclusion

We reject all of Thomas’s substantive challenges to his 

sentence. We remand the case to the district court so it may 

consider his claims that he received ineffective assistance of 

counsel due to counsel’s failure to (1) argue for or present facts 

supporting a Smith variance, or object to the district court’s 

reasons for rejecting one, (2) raise mitigating facts contained in 

the Government’s sentencing exhibits, (3) review the 

sentencing exhibits with Thomas, and (4) submit character 

letters Thomas’s family and friends had written. 

So ordered.
KAREN LECRAFT HENDERSON, Circuit Judge, concurring:

I write separately to record my view that the district court 

“scrupulously adhere[d] to the obligations of Rule 11,” United 

States v. Shemirani, 802 F.3d 1, 3 (D.C. Cir. 2015), including 

the requirement to “inform the defendant of, and determine that 

the defendant understands, . . . the terms of any plea-agreement 

provision waiving the right to appeal or to collaterally attack 

the sentence,” Fed. R. Crim. P. 11(b)(1)(N). Accordingly, 

although I join the rest of my colleague’s opinion for the Court, 

I depart from his conclusion that “whether the district court 

fundamentally mischaracterized the waiver provision is a close 

call.” Op. at 13.

An appeal waiver is generally enforceable. See United 

States v. Guillen, 561 F.3d 527, 529 (D.C. Cir. 2009). But if a 

judge mischaracterizes the waiver “in a fundamental way”—at 

least in a way that benefits the defendant—“‘the district court’s 

oral pronouncement controls.’” United States v. Godoy, 706 

F.3d 493, 495–96 (D.C. Cir. 2013) (quoting United States v. 

Buchanan, 59 F.3d 914, 918 (9th Cir. 1995)). This doctrine 

naturally follows from the premise that criminal defendants

“need to be able to trust the oral pronouncements of district 

court judges.” Buchanan, 59 F.3d at 918. If applicable only to 

a genuine mischaracterization, the doctrine fulfills a primary

purpose of Rule 11—namely, ensuring that the defendant’s 

waiver is knowing and voluntary. See Shemirani, 802 F.3d at

2 (citing United States v. Vonn, 535 U.S. 55, 62 (2002)). An 

appellate court, however, should not use a magnifying glass to 

scrutinize a minor change in phraseology that nonetheless jibes

with the written document, whether or not it benefits the 

defendant.

Rule 11, after all, “does not say that compliance can be 

achieved only by reading the specified items in haec verba.” 

United States v. Saft, 558 F.2d 1073, 1079 (2d Cir. 1977) 

(Friendly, J.). “To the contrary, a lifeless recitation of the plea 

agreement is disfavored.” Op. at 12. In an ideal plea colloquy, 
2

the judge explains, rather than recites, the waiver provision. As 

my colleague notes, this requires striking a “delicate balance.” 

Id. The judge should “[p]rovide enough explanation to dispel 

any misunderstanding without simply reading the agreement 

aloud, but in doing so, take care not to create a new or different 

misconception that effectively amends the written agreement.” 

Id.

The district judge struck that balance appropriately here. 

Under the plea agreement, Thomas waived his right to appeal 

his sentence “except to the extent the Court sentence[d] [him] 

above the statutory maximum or guidelines range determined 

by the Court.” Summarizing this language during the plea 

colloquy, the district judge told Thomas that he was waiving 

his right to appeal “unless you are sentenced to a period of 

imprisonment longer than the statutory maximum or the Court 

departs upward from the applicable recommended sentencing 

guideline range[,] which is all set out in your plea letter at page 

7, paragraph 10.”

Granted, “unless” and “except to the extent” do not have 

identical meanings. Unless denotes an exception; except to the 

extent also denotes an exception but introduces detail about the 

scope of the exception. In other words, unless is “less precise 

and broader than” except to the extent. Op. at 13. 

Notwithstanding the district court’s summary informed 

Thomas that he would regain certain appeal rights should he 

receive an above-Guidelines sentence, it failed to identify 

which appeal rights would be restored. Certainly the court 

could have—and perhaps should have—explained that an 

above-Guidelines sentence would not vitiate the appeal waiver 

in toto. But, in my view, its failure to do so falls far short of a 

mischaracterization, let alone a fundamental 

mischaracterization.
3

Faulty-colloquy cases are repeat offenders in our Court so 

we have a good basis to make comparisons. We have issued at 

least five published opinions holding that the district court’s 

oral pronouncement contradicted the terms of a written appeal 

waiver. See, e.g., Godoy, 706 F.3d at 495; United States v. 

Fareri, 712 F.3d 593, 594 (D.C. Cir. 2013); United States v. 

Kaufman, 791 F.3d 86, 88 (D.C. Cir. 2015); United States v. 

Hunt, 843 F.3d 1022, 1028 (D.C. Cir. 2016); United States v. 

Brown, 892 F.3d 385, 395–96 (D.C. Cir. 2018) (per curiam). 

All but one—Fareri is the exception—address waiver terms 

that are similar or identical to the language in Thomas’s plea 

agreement.

In Godoy, the judge told the defendant that he could appeal 

his sentence if “the Court has done something illegal, such as 

imposing a period of imprisonment longer than the statutory 

maximum.” 706 F.3d at 495 (emphasis omitted). Although the 

government argued that a reasonable person would interpret 

“such as” to mean “limited to,” we rejected the argument. See 

id. In Kaufman, the judge told the defendant that he could 

appeal “if [he] believe[d] the sentence is illegal” or if he did 

not “like” the sentence. 791 F.3d at 88 (alterations in original). 

Hunt was similar. 843 F.3d at 1025. And in Brown, the judge

told the defendant that he could appeal “on the grounds of 

reasonableness.” 892 F.3d at 395. But see id. at 410 

(Kavanaugh, J., dissenting in part) (district judge noted appeal 

would apply only “with regard to certain circumstances”). 

Each of these statements, “[t]aken for [their] plain meaning—

which is how criminal defendants should be entitled to take the 

statements of district court judges,” Godoy, 706 F.3d at 495—

arguably led the defendant to think that he had a broader right 

to appeal than the plea agreement promised.

Nothing of that sort happened here. Although the district 

court’s pronouncement was less detailed than the written 
4

agreement, it did not mischaracterize that agreement. 

Moreover, the district judge’s words had other virtues. 

“Unless” is a crisp and simple word. Its use made plain what 

might be obscured by the more complex “except to the extent” 

formulation: the precise condition that would resurrect 

Thomas’s appeal rights.

Moreover, were we inclined to fault the district court for 

omitting detail, that would not automatically merit reversal. If 

a judge’s complete failure to discuss the appeal waiver does not 

necessarily constitute reversible error, see United States v. Lee, 

888 F.3d 503, 506 (D.C. Cir. 2018), neither does a single 

change in phraseology. What matters is whether Thomas 

understood what he was giving up. I agree that “[t]he natural 

understanding” of the district court’s pronouncement “is that 

the right retained is the right mentioned—that is, the right to 

appeal the upward departure.” Op. at 13. A “natural 

understanding” is the best evidence of what Thomas “might 

reasonably have understood the court to mean,” Hunt, 843 F.3d 

at 1028, even if an alternative meaning—no matter how 

implausible—might literally be consistent with the court’s 

words.

Labeling the district judge’s words a “close call” may also 

have an unintended effect on judges who, notwithstanding our

admonition to the contrary, may decide that the safest course is 

to recite appeal waivers verbatim. This, too, would hurt 

criminal defendants, most of whom are not lawyers and may 

struggle to comprehend “the dark emptiness of legal jargon.” 

Fisher v. United States, 328 U.S. 463, 487 (1946) (Frankfurter, 

J., dissenting). But a judge who simply reads the text of the 

appeal waiver is unlikely to be reversed, Saft, 558 F.2d. at 

1079—even though Rule 11’s purpose would be frustrated—

thus a “lifeless recitation” is what we may come to expect.