IN THE UNITED STATES COURT OF APPEALS

FOR THE FIFTH CIRCUIT

No. 11-50482 

cons. w/ 11-50484

UNITED STATES OF AMERICA,

Plaintiff-Appellee,

v.

ADRIAN EDWARDO PENA, also known as Adrian Edward Pena,

Defendant-Appellant.

Appeals from the United States District Court

for the Western District of Texas

Before STEWART, Chief Judge, and SMITH and WIENER, Circuit Judges.

CARL E. STEWART, Chief Judge:

This case entails two appeals from Defendant-Appellant Adrian Pena’s

convictions and sentences for criminal offenses related to the bribery of two

public officials to procure a multimillion dollar construction contract. Pena

contends on appeal that the district court violated Federal Rule of Criminal

Procedure 11(c)(1) by participating in his plea negotiations. Pena also asserts

that the court’s involvement caused his trial attorney, Thomas Stanton, to

represent him under an actual conflict of interest which adversely affected

Stanton’s performance. Based on this alleged conflict of interest, Pena filed a

motion to withdraw his guilty pleas, which the court denied. Pena appeals his

convictions and sentences, as well as the district court’s denial of his motion to

United States Court of Appeals

Fifth Circuit

F I L E D

June 18, 2013

Lyle W. Cayce

Clerk
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1

In January 2010, Jeffrey C. Stone, Inc., filed suit against SDVO, Nunez, Pena, Pena’s

wife, and others, alleging that the defendants breached a teaming contract between Jeffrey

Stone and SDVO and committed various acts of misrepresentation and fraud in relation to the

Arizona project. SDVO, Nunez, and the Penas were represented by local counsel and by

Stanton in that proceeding. 

2

withdraw his guilty pleas. We VACATE Pena’s guilty pleas and sentences, and

REMAND for further proceedings.

I. FACTUAL BACKGROUND & PROCEDURAL HISTORY

A. The Instant Offenses

In 2009, Pena was arrested in El Paso, Texas, and was charged in two

separate indictments for conspiracy to commit mail fraud, mail fraud, and

deprivation of honest services of a public servant. The charges arose from Pena’s

employment with the construction company for which he worked until 2007.

Both indictments alleged that Pena paid bribes to El Paso County officials to

obtain a multimillion dollar construction contract for that former employer.

Stanton represented Pena in both cases. 

B. Other Proceedings Involving Pena

At the same time that Pena was facing these charges, he was working for

the construction firm of his father-in-law Carlos Nunez, SDVO Contractors,L.P.

(“SDVO”). SDVO was involved in three controversies regarding an Arizona

construction project for the Department of Defense (DOD)—two civil lawsuits

and one criminal investigation:

1) Jeffrey C. Stone, Inc. v. SDVO1: a civil matter in

Arizona, in which Pena was a named individual

defendant;

2) Bank of the West v. SDVO Contractors, LP: a civil

matter that was proceeding before Judge

Montalvo, where Stanton represented SDVO; and
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3

3) A criminal investigation into the Arizona project

that potentially implicated Pena and several of

Stanton’s civil SDVO clients.

The litigation surrounding the Arizona project arose from the DOD’s

erroneous transfer of funds into SDVO’s bank account and SDVO’s subsequent

withdrawal of most ofthose funds. Specifically, in April 2010, the United States

Property and Fiscal Officer for the Arizona National Guard (USPFO) issued a

termination-for-default notice to SDVO, ending the contract for the Arizona

project. As a result of this termination, the USPFO demanded that the surety

perform its obligation under the performance bond. In June 2010, however, the

USPFO inadvertently wired a $733,720 payment for the project into SDVO’s

account atthe Bank ofthe West(“the Bank”), not into the surety’s bank account.

When the surety and the USPFO realized the error and contacted the Bank to

reverse the transaction or freeze the funds,the Bank advised that the funds had

already been disbursed in their entirety, with the exception of an IRS levy placed

on the accountin the amount of approximately $159,000. In July 2010,the Bank

filed a state interpleader action for the $159,000, naming as defendants SDVO,

the IRS, and the DOD. After this interpleader action was removed to federal

court, Stanton appeared as counsel for SDVO. 

The criminal investigation relating to the Arizona construction project

involved SDVO’s alleged misappropriation of these same funds. 

C. Pre-trial Proceedings for the Instant Offenses

In July 2010, an Assistant United States Attorney (“AUSA”) informed

Stanton of an ongoing Arizona criminal investigation into SDVO. The AUSA

notified Stanton that, because of that investigation, Stanton might have a

conflict of interest in representing SDVO and Nunez in any criminal matters

because of Stanton’s representation of Pena in the instant proceedings. In
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4

response to this information, Stanton affiliated separate criminal defense

counsel for SDVO and Nunez.

During this same time, the government also filed a notice of its intention

to use evidence of other crimes, wrongs, or acts for the instant proceedings,

pursuant to Rule 404(b) of the Federal Rules of Evidence. Specifically, the

government sought to adduce evidence that, in January 2010, Pena contacted a

subcontractor on the Arizona project on behalf of SDVO to discuss a possible

kickback of contract funds. In August 2010, a pretrial services officer sent the

district court a memorandum advising that a recent FBI report contained

allegations that, while out on bond, Pena had misappropriated the funds

inadvertently deposited into the SDVO bank account. The court however took

no action adverse to Pena as a result of this report. 

D. Plea Negotiations andthe Court’s Reference to the “SDVO Matter”

On December 1, 2010, the district court held a chambers conference with

the attorneys, which the court neither recorded nor transcribed. At that

conference, Stanton told the district court that Pena and the government were

engaged in plea negotiations and that Stanton expected those negotiations would

be successful. The district court’s response to this information is the focal point

of this appeal. 

There are three different versions of the district court’s response. First,

Stanton’s filing on the same day as the chambers conference suggests that the

court said it wanted Pena to resolve the SDVO matter before the court would

accept Pena’s plea. According to Stanton, the court told him that it had received

information that money related to SDVO had been “missing and misapplied.”

Second, the government recalls the district court saying that it would give Pena

full credit for acceptance of responsibility if he resolved the SDVO matter

concurrently with his guilty plea to the instant offenses. Third, at a hearing in
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5

May 2011, the district court stated on the record that it recalled saying that the

SDVO matter should be “resolved concurrently with the resolution of this case.”

Likewise, the district court’s order following the hearing states: “At the

conference the Court mentioned [the SDVO interpleader action] and stated its

opinion that the civil case should be resolved by the time of the plea hearing [for

the instant offenses].” Following the court’s statements, Stanton asked for the

opportunity to respond to the allegations, but the court denied this request.

E. Stanton’s Conflict-of-Interest Claim and Motion to Withdraw as

Counsel

On the same day as the chambers conference, Stanton notified Pena via

email that he (Stanton) might have a non-waivable conflict in representing both

Pena and SDVO. Pena responded that he could not allow Stanton, “under any

circumstances,” to cease representing him in the SDVO matters. Pena then

appears to have told Stanton that he would continue pro se in the instant

criminal matters. Pena wrote that he would not sign the plea agreement unless

it included the condition the district court had imposed and that he would

request that the prosecutor enforce the condition.

Later that day, Stanton filed a motion under seal notifying the district

court of his conflict of interest and asking the court to vacate the trial date and

permit him to withdraw from Pena’s case. Stanton reminded the court that he

represented SDVO in the interpleader action regarding the same monies the

court mentioned in chambers, which was pending in the same judge’s court. In

addition, the Jeffrey Stone case was pending in Arizona, and that case also

“involve[d]the construction project made the basis of the Government’s payment

to SDVO.” Although Stanton had obtained separate counsel to represent SDVO

and Nunez, he “continue[d] to be one of three lawyers representing SDVO in

several [civil] matters.” Stanton reasoned that, because he continued to
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2 A minute entry on the docket reflects that the court denied Stanton’s motion to

withdraw on December 3, 2010. However, the court’s sealed order dated May 18, 2011 notes

that “the electronic file notation denying Stanton’s Motion to Withdraw . . . was not entered

until May 11, 2011”–five months after Pena pleaded guilty.

6

represent SDVO and because the district court had ordered that the SDVO

matter pending before it be resolved before it would accept Pena’s plea

agreement, Stanton was ethically required to: 1) notify Nunez, SDVO, and Pena

of his conflict of interest; 2) inform Nunez that he could not waive the conflict as

it affected Pena; 3) withdraw from the SDVO litigation; and 4) withdraw from

representing Pena. Stanton stated that, although he could not disclose the full

extent of the conflict, he could not recommend that Pena accept terms that

Stanton could not accomplish ethically and that were unenforceable.

Stanton also told the district court that, in response to the chambers

conference, Pena had directed him to remain as his counsel in the SDVO

litigation, but that Stanton believed this request was against both Pena’s and

Stanton’s interests. Stanton asked the court to: 1) vacate the trial date; 2)

recuse itself or reassign the case; 3) permit Stanton to withdraw; 4) accept the

plea based on the terms the parties had discussed prior to the chambers

conference; and 5) not factor in the SDVO litigation for any sentencing matters.

The district judge’s law clerk phoned the parties the next day, December

2, 2010. The law clerk told the parties that the court had changed its mind

about the need to resolve the SDVO matter before the court would accept Pena’s

plea and that the parties were to “disregard” its statement.2

F. Plea Agreements and Guilty Plea Hearing

Four days later, on December 6, 2010, Pena signed plea agreements in

both cases, admitting to the conspiracy charges in the first count of each

indictment. The government agreed to ask that Pena not be sentenced until he
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3 Pena later attached these letters as exhibits to his pro se motion to continue the

sentencing and replace counsel, which he filed on April 15, 2011.

7

had been fully debriefed so that the government might request a lower sentence

under U.S.S.G. § 5K1.1 for substantial assistance. 

During the hearing, the district court followed the standard plea colloquy

procedure under Rule 11. The court was also especially concerned about Pena’s

“duty of financial candor,” which was a condition of his plea agreement: 

THE COURT: Mr. Pena, before I preliminarily accept

your guilty plea, I need to direct your attention to the

duty of financial candor section contained in both plea

agreements in both of these cases. . . . I am going to

instruct my probation officer within ten days oftoday to

set up a meeting with you in which you are going to

disclose the totality of your financial dealings, who have

you given money to recently, say in the last year, that

is out of the ordinary. Anything that that [sic]

probation officer asks you about your finances, you are

going to answer.

Pena confirmed his understanding of these terms. The court subsequently

accepted Pena’s guilty pleas and set sentencing for April 20, 2011.

G. Pena’s Pro Se Activity Related to His Debriefings and Sentencing

Prior to Pena’s sentencing, he engaged in significant pro se activity related

to his debriefings with the government and his upcoming sentencing. For

example, Pena, pro se, sent various communications to the probation officer,

including:3

• In a letter to the probation officer dated February 2,

2011, Pena lodged legal challenges to the factual basis

for his plea, arguing, inter alia, that the facts did not

match the indictment. 

• In a February 11, 2011 letter to the probation officer,

Pena expressed frustration that he had been unable to

fully comply with his plea. He pointed to the plea
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8

agreement’s “duty of financial candor” section to

illustrate that he was attempting to comply with the

district court’s demand that he resolve the SDVO

matter. He wrote that he had insisted “the court’s

request to ‘resolve the SDVO matter’. . . prior to having

plead [sic], but my attorney and the AUSA refused to

include the resolving of the SDVO matter in my plea.”

Pena also referred to his debriefings, his duty of

financial candor in his plea agreement, and the court’s

request to resolve the SDVO matter, writing, “I WANT

TO CONTINUE TO COMPLY!”

• On March 14, 2011, Pena submitted “Self-Provided

Presentencing Supporting Information” to assist the

probation officer with composing his presentence

investigation report (“PSR”). 

• Also on March 14, Pena wrote to the probation officer:

“For the Record, I have provided ‘Substantial

Assistance,’ but unfortunately without Counsel. I do

not and never wish to have or be represented especially

during any debriefings. In respecting the Court’s

Demand to resolve certain matters, I have been without

counsel and do not wish to ever waive this right.” 

In virtually all of his pro se communications, Pena indicated that he was without

counsel and requested assistance from the probation officer.

H. Pena’s Pro Se Conflict and Judicial Participation Claims, and

Pena’s Request to Withdraw His Plea

On April 15, 2011, Pena, pro se, filed a motion to continue sentencing and

replace counsel, to which he attached copies of the above-referenced

communications, in addition to others. In the documents, Pena asserted that the

PSR that the probation officer had recently filed evidenced an ongoing conflict

between Pena and Stanton. The PSR listed the SDVO matter under “Pending

Charges.” The PSR also contained information that some of the SDVO monies

had been transferred to Stanton’s Interest on Lawyer’s Trust Account
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If a lawyer holds any funds which do not belong to the lawyer, then those funds must

be held in a separate account designated as “trust” or “escrow,” which is the purpose of the

IOLTA. See Tex. Disciplinary R. Prof’l Conduct 1.14(a).

9

(“IOLTA”).4 Pena explained that these funds were the source of Stanton’s

conflict of interest, both because Stanton was operating under a duty to protect

the funds on behalf of SDVO in the civil suit and because there was an ongoing

criminal investigation into these same funds which potentially implicated

Stanton and his SDVO civil clients.

Pena also pointed out that he had already begun extensive debriefings

with the government in the hope of favorable treatment at sentencing, but that

Stanton was not present at about 80 percent of those debriefings. According to

Pena, Stanton did not attend the debriefings “due to the conflict with the court

requested SDVO resolution.” He wrote: “Defendant’s Counsel cannot fight,

rebut[ ] and/or respond to the prosecution [to reap the benefits [of]the 5K section

and substantial assistance section] because of the inability to explain in detail

to the court all of the information provided to the prosecution about SDVO by

defendant.” In one of the attachments, Pena stated that Stanton “cannot

effectively represent me when discussions ONLY about my old employer SDVO

are taking place.”

In its response to Pena’s motion, the government stated its belief that the

fact that Pena continued with plea negotiations after the court withdrew the

SDVO condition suggested that no harm had been done. The government

maintained that the district court was under no obligation to investigate

Stanton’s and Pena’s claims that Stanton was conflicted in the case because

Pena had pointed to no actual conflict. According to the government, Stanton’s

representation of SDVO did not render him conflicted in the matter of Pena’s

debriefings because the government, not defense counsel, decides whether a

defendant has debriefed truthfully and fully. 
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10

In his reply to this motion, Pena requested to withdraw his guilty plea

because he had pled on the advice of conflicted counsel. In this filing, he twice

referred to the district court’s “inserting itself into plea negotiations” as the

cause of the conflict. He wrote: “The court was knowingly aware of the potential

conflict by motion, within 13 hours of defendant’s counsel’s known awareness

thatthere was in fact a potential conflict made by the courtinserting itself in the

plea negotiations of December 1, 2010 and making its knowledge of the conflict

known.” He also wrote: “On December 1, 2010 defendant’s counsel was made

aware of the potential conflict by which the court inserted itself in the plea

negotiations at the Chamber’s Conference held.”

The government responded separately to Pena’s request to withdraw his

pleas, arguing that, at the plea colloquy, Pena said he was pleading knowingly

and voluntarily and that he was satisfied with his counsel: The government

indicated its beliefthatthe court had complied with Rule 11 during the colloquy.

The government also noted that Pena had not asserted that he was not guilty of

the charges.

I. Stanton’s Post-plea Conflict Claims

In Stanton’s separate filing on April 18, 2011, he renewed his request to

withdraw as counsel. He stated: “I agree [with Pena] that I have a conflict

consistent with my representations to the Court under seal on December 1, 2010.

However, until the Court makes a determination, I am ethically bound to file on

behalf of Mr. Pena objections”to the PSR. Stanton wrote that he was proceeding

even though, on the same day as his filing, Pena “reaffirmed to [Stanton] to not

proceed in his defense because of the conflict of interest . . . that he has not

waived.”

Stanton objected, inter alia, to the PSR’s inclusion of matters regarding

the disputed SDVO monies and inaccuracies relating to this information.
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5 On that same day, the docket was amended to reflect that the district court had

denied the first motion to withdraw on December 3, 2010.

11

Stanton told the court that the paragraphs alleging that Pena had

misappropriated funds raise a conflict of interest because Stanton represented

SDVO and Carlos Nunez in civil matters directly related to these matters.

SDVO had waived a conflict of Stanton’s representation of Pena only “so long as

the representation does not bar [Stanton] from proceeding in the defense of

SDVO and Nunez on the civil matters.” Stanton also stated that he had

“proceeded in representation on the two guilty pleas in reliance on the Court’s

statement to disregard the matters the Court raised sua sponte relating to

SDVO.” He asked the court to strike the paragraphs relating to SDVO,

“consistent with the Court’s statement to [Stanton] to disregard its earlier

requirement that the SDVO matters be resolved.”

J. Hearing on Pending Motions to Withdraw Counsel and to

Withdraw Guilty Plea

The district court held a hearing on May 11, 2011.5 The court said that,

in its view, it had mooted Stanton’s post-conference conflict claim when it

notified the parties that it was withdrawing its requirement that the SDVO

litigation be resolved before it accepted Pena’s plea. It noted that Pena had

pleaded guilty and ordered the probation officer to prepare an amended PSR to

remove references to the SDVO “because, frankly, it is erroneously referred to

as a pending charge, and it is not.”

Pena represented himself at this hearing, although Stanton was also

present. Pena told the district court that Stanton’s conflict arose from the

criminal investigation into SDVO. He said that, based on his debriefings with

the government, he understood that the investigation was continuing and that

he was a target. The subject matter of the investigation, Pena pointed out, was
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12

missing funds, “the funds that [had] been deposited into [Stanton’s] trust.” 

Pena told the court that Stanton “could have possibly been working under the

loyalty of protecting the funds, the funds that belong to an employer, or

protecting the company.” 

When offered an opportunity to speak, Stanton stated:

Your honor, my ethical requirements are to not take a

position inconsistent with my client. The Court has

before it my notice to the Court in response to his

motion to withdraw. The Court directed me to remain

his counsel. I am doing so. And I have nothing further

to add today. 

The district court advised Pena that it would not consider anything

relating to the SDVO civil case or any pending criminal investigation in

determining Pena’s sentence. The district court confirmed that, after Stanton

filed his December 1, 2010 motion to withdraw, he received notification,through

the judge’s law clerk, that the judge would not consider the SDVO matter with

respect to Pena’s guilty pleas. The district court described the conflict as an

“obscurely described potential conflict having to do with an investigation out

there.” It stated that it would not factor in the investigation at sentencing. At

the end of the hearing, the district court, sua sponte, revoked Pena’s bond in the

beliefthat Pena’s pro se motions evidenced his failure to accept responsibility for

his actions.

The district court denied Pena’s pro se motions in a subsequent sealed

order on May 18, 2011. This order reflected the court’s oral statements at the

hearing that it did not believe Pena had pointed to an actual conflict. The court

also characterized any conflict stemming from the government’s intent to use the

Rule 404(b) evidence as “hypothetical.” In relevant part, the order stated:

Pena appears to conflate three distinct SDVO matters.

Bank of West v. SDVO Contractors . . . is a civil case

currently pending before this Court. The Court
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conducted an in-chambers conference with both parties

on December 1, 2010. At the conference the Court

mentioned this civil case and stated its opinion that the

civil case should be resolved by the time of the plea

hearing. After further deliberation, the Court decided

the civil case was proceeding in a timely manner and

there was no reason to impose such a requirement. . . .

The third SDVO matter is an apparent criminal

investigation in Arizona. The Court gleaned

information about the third SDVO matter from the

United States Pretrial Services . . . On August 3, 2010,

Pretrial Services sent a Memorandum to the Court

reporting a possible bond violation by Pena. . . . The

information related to conduct of Pena in connection to

SDVO.

The district court concluded: “Pena does not identify how simultaneously

representing SDVO in a civil matter and Pena in the above-captioned criminal

cases present a conflict.” The court also concluded that Pena’s plea colloquy

demonstrated that his pleas were knowing and voluntary, and that he was

satisfied with his counsel’s representation. The court then denied Pena’s

motions requesting to replace counsel and to withdraw his guilty pleas.

K. Sentencing

At the sentencing hearing, the court first established that Pena did not

have Stanton or other counsel present with him atthe PSR interview. The court

then sentenced Pena to a total of 76 months of imprisonment, consisting of two

63-month terms, with 13 months in one case to be served consecutively to the

sentence imposed in the other. The court also ordered that Pena serve

concurrent three-year terms of supervised release and fined him $125,000 in

each case (for a total fine of $250,000).

Pena timely appealed both of his convictions and sentences. These appeals

have been consolidated for our consideration.
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6 Westlaw and Lexis have designated United States v. Adams as “superseded” by

statute or regulation based on the reasoning of non-Fifth Circuit cases that Adams was decided

prior to the enactment of the U.S. Sentencing Guidelines. However, we have relied on Adams

in full, including its remedy, as recently as 2010. See United States v. Self, 596 F.3d 245, 250

(5th Cir. 2010) (relying on Adams to vacate the defendant’s conviction and sentence and to

reassign to a different judge on remand following the district court’s participation in plea

negotiations). Thus, while these sources categorize Adams as no longer good law in part, this

designation is incorrect.

14

II. DISCUSSION

A. Judicial Participation in Plea Negotiations

1. Applicable Law

Rule 11 allows a district court to accept or reject a plea agreement. Fed.

R. Crim. P. 11(c)(4) - (5). Further, “a court must be free, in certain respects, to

take an ‘active role’ once the agreement is disclosed.” United States v. Miles, 10

F.3d 1135, 1140 (5th Cir. 1993) (citation omitted). In fact, the rule mandates

this scrutiny. See id. (citations omitted). Rule 11 also requires that the district

court “address the defendant personally in open court and determine that the

plea is voluntary and did not result from force, threats, or promises (other than

promises in a plea agreement),” and “determine that there is a factual basis for

the plea.” Fed. R. Crim. P. 11(b)(2), (b)(3).

However, Rule 11 prohibits the sentencing court from participating in plea

negotiations: “An attorney for the government and the defendant’s attorney, or

the defendant when proceeding pro se, may discuss and reach a plea agreement.

The court must not participate in these discussions.” Fed. R. Crim. P. 11(c)

(emphasis added). We have characterized Rule 11’s prohibition of judicial

involvement as a “brightline rule,” UnitedStates v. Rodriguez, 197 F.3d 156, 158

(5th Cir. 1999), and “an absolute prohibition on all forms of judicial participation

in or interference with the plea negotiation process,” United States v. Adams,

634 F.2d 830, 835 (5th Cir. Unit A Jan. 1981).6 Thus, while the rule “requires

that a district court explore a plea agreement once disclosed in open court[,] . . .
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it does not license discussion of a hypothetical agreement that it may prefer.”

Miles, 10 F.3d at 1140 (citation omitted).

We have recognized this bright line rule for several reasons. First, “it

serves to diminish the possibility of judicial coercion of a guilty plea, regardless

of whether the coercion would cause an involuntary, unconstitutional plea.” Id.

at 1139 (citations omitted). Indeed, “pressure is inherent in any involvement by

a judge in the plea negotiation process.” Rodriguez, 197 F.3d at 159. Second,

“such involvement ‘is likely to impair the trial court’s impartiality. The judge

who suggests or encourages a particular plea bargain may feel a personal stake

in the agreement . . . and may therefore resent the defendant who rejects his

advice.’” Miles, 10 F.3d at 1139 (omission in original) (citations omitted). Third,

a judge’s “participation in plea discussions creates a misleading impression of

the judge’s role in the proceedings. As a result of his participation, the judge is

no longer a judicial officer or a neutral arbiter.” Id. (citations and internal

quotation marks omitted). Rather, the judge “becomes or seems to become an

advocate for the resolution he has suggested to the defendant.” Id. (citations and

internal quotation marks omitted).

2. The Parties’ Arguments

Pena alleges that the district court violated Rule 11 when it participated

in plea negotiations by stating that Pena should resolve the “SDVO matter”

before the court would accept his guilty plea for the instant offenses. Pena

argues that the court improperly proposed a “hypothetical agreement,” as it

“attempted to resolve a pending civil matter and possible criminal allegations

against Pena by conditioning acceptance of Pena’s plea on resolution of those

matters.” 

The government maintains thatthe district court’s comments “did not rise

to the level of participation,” as they “are best characterized as an off-the-cuff
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attempt to shape the administrative conditions under which it would accept the

plea itself, and not an injection into the discussion of the terms of the

agreement.”

3. Discussion

Given the sanctity of Rule 11’s absolute prohibition on any form of judicial

involvement in plea negotiations, we conclude that, albeit unintentionally, the

district court here stepped over the line and violated Rule 11 when it suggested

that Pena must resolve the SDVO matter before the court would accept Pena’s

plea in the instant offenses. See Crowell, 60 F.3d at 203 (citing Miles, 10 F.3d

at 1139-40) (“When a court goes beyond providing reasons for rejecting the

agreement presented and comments on the hypothetical agreements it would or

would not accept, it crosses over the line established by Rule 11 and becomes

involved in the negotiations.”)).

As noted, Pena and the government present different accounts of exactly

what the district court said during the off-the-record chambers conference, in

addition to the court’s own assertion of what it said. Pena asserts that the

district court said that it would not accept a plea unless Pena first resolved the

SDVO matter by returning monies that the district court believed Pena had

misappropriated. The government asserts that the district court said it would

give Pena full credit for acceptance of responsibility if he resolved the SDVO

matter concurrently with his plea in the instant proceedings. The government

also maintains that the specific SDVO matter that the court referred to was the

interpleader action, which was also pending before the district court. The

district courtlikewise suggested at both the hearing and in its order in May 2011

that it told Pena that he should resolve the civil interpleader action prior to

pleading guilty to the instant offenses. Regardless, we agree with Pena that any
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17

version constitutes participation in plea negotiations in violation of Rule 11, for

several reasons. 

First, the district court’s statements connote the possibility that the court

had already made a determination as to Pena’s guilt in the instant offenses and

preferred a guilty plea. See Rodriguez, 197 F.3d at 160 (“The clear implication

of the judge’s statements at the pretrial hearing was that the judge desired a

plea.”); Miles, 10 F.3d at 1141 (“By trying to facilitate a plea bargain, the judge

indicated that he desired an agreement; this is pressure enough.” (quoting

United States v. Barrett, 982 F.2d 193, 196 (6th Cir. 1992))). In particular, both

the government’s and the district court’s versions of the court’s statements would

constitute the court’s own plea bargain. See Adams, 634 F.2d at 836 (concluding

that the district court participated in plea negotiations when “the judge offered

a plea bargain to [the defendant] on her own initiative”). The district court’s

statements also implied that Pena was liable for wrongdoing, i.e.,

misappropriating funds, in an unrelated matter.

Second, the fact that the court made the statements while plea

negotiations between Pena and the government were ongoing is crucial: We

have noted the distinction between a sentencing court’s comments before the

parties have disclosed the terms to the court and the court’s statements after

this time. See Crowell, 60 F.3d at 204. For instance, in Crowell, the district

court’s comments reflected its “feeling that a penalty significantly more severe

than that allowed under the first plea agreement would be necessary for an

agreement to be acceptable,” which the court made known to the parties before

the second agreement was in final form. Id. at 204. We stated, “the fact that

this comment was injected into the discussions while the parties were still

preparing the second agreement is critical. It is precisely this type of

participation that is prohibited by Rule 11.” Id.
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The instant case is similar to United States v. Daigle, in which we

concluded that the district court erred by participating in plea negotiations when

it engaged in an off-the-record discussion with the parties in chambers regarding

the defendant’s guilty plea and sentence. 63 F.3d 346, 347 (5th Cir. 1995).

During the chambers conference in Daigle, the district court informed the

defendant that, if “he fully cooperated, that 90% of the time [the court] will

follow the [sentencing] recommendation of the U.S. Attorney.” Id. at 347, 349.

The defendant understood this statement to mean a nine-year “cap” of prison

time based on the court’s statements during the subsequent guilty plea hearing.

Id. at 348. At that hearing, the court stated: “All right, so if nine years is what

y’all agreed upon and that’s the recommendation made to me, and there is

substantial cooperation, that’s the cap of nine years, okay?” Id. at 348-49. We

concluded that the district court participated in the plea negotiations based on

the court’s statement that it follows the government’s sentencing

recommendation “90% of the time” if the defendant cooperates. Id. at 349. We

noted thatthe district court’s statement during the hearing “strongly support[ed]

[the defendant’s] contention that he understood the court to be indicating a ‘cap’

of nine years if the government so recommended.” See id. at 348-49. 

Here, the government’s principal argument against the conclusion that the

district court’s statements constituted involvementis thatthe comments “did not

rise to the level of participation.” Rather, insists the government, the

statements “are best characterized as an off-the-cuff attempt to shape the

administrative conditions under which it would acceptthe plea itself, and not an

injection into the discussion of the terms of the agreement.” Commendably,

however,the government also concedes that Pena’s interpretation of the district

court’s statements is reasonable–that they reflected the court’s insertion of a

“condition” into the terms of his plea. See, e.g., United States v. Ekwerekwu, No.
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93-9126, 1995 WL 136519, at *3 (5th Cir. Mar. 17, 1995) (vacating and

remanding the defendant’s conviction and sentence after concluding that the

district court participated in plea negotiations and noting that we “must

appropriately consider Ekwerekwu’s reasonable perception” of the district court’s

potential lack of objectivity). It is also noteworthy that the government’s

argument on this issue focuses more on the harmlessness of the court’s

statements than on whether the statements constituted error under Rule 11 in

the first instance. 

We conclude thatthe district court participated in Pena’s plea negotiations

in violation of Rule 11. Although the record discloses no basis to conclude that

the court’s error was intentional, we nevertheless must heed Rule 11’s brightline prohibition of all judicial participation in plea negotiations and recognize the

district court’s error. See Barrett, 982 F.2d at 196 (“Regardless of the judge’s

objectivity, it is the defendant’s perception of the judge that will determine

whether the defendant will feel coerced to enter a plea.”) (citation omitted). This

error was plain in light of our well-settled circuit law prohibiting a court’s

participation in plea negotiations.

B. Effect on Pena’s Substantial Rights

While the parties dispute whether harmless error or plain-error review

applies in this case, we pretermit a determination of this issue. Even assuming

arguendo that plain-error review applies, we conclude that we must exercise our

discretion to reverse the district court.

1. Applicable Law

Under the Federal Rules of Criminal Procedure, “[a] plain error that

affects substantial rights may be considered even though it was not brought to

the court’s attention.” Fed. R. Crim. P. 52(b); see United States v. Vonn, 535 U.S.

55, 58-59, 62, 74 (2002) (applying plain-error review to unpreserved Rule 11
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20

error, notwithstanding Rule 11’s provision that a variance from the

requirements of the rule is harmless error ifthe error does not affect substantial

rights (citing Fed. R. Crim. P. 11(h))); see also United States v. Davila,

No. 12-167, 569 U.S. ___, 2013 U.S. LEXIS 4541, at *24-25 (U.S. June 13, 2013)

(reaffirming that plain-error review, rather than automatic vacatur, governs

unpreserved Rule 11 error). “To affect the defendant’s substantial rights, the

defendant must demonstrate that the error affected the outcome of the district

court proceedings.” United States v. Broussard, 669 F.3d 537, 553 (5th Cir.

2012) (citations omitted). “[A] defendant who seeks reversal of his conviction

after a guilty plea, on the ground that the district court committed plain error

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

would not have entered the plea.” United States v. Dominguez Benitez, 542 U.S.

74, 83 (2004). Lastly, under the final prong of plain-error review, “[w]e will

exercise our discretion to correct plain error if it seriously affected the fairness,

integrity, or public reputation of the judicial proceeding.” Broussard, 669 F.3d

at 553 (alteration in original) (citation omitted).

2. The Parties’ Arguments

Pena contends that three things are evident from the record: 1) The

district court’s condition was inherently coercive and became the focal point of

the plea negotiations; 2) that condition created or revealed a conflict of interest

between Pena and Stanton; and 3) neither the court’s attempt to withdraw its

condition nor Pena’s guilty plea could ameliorate the harm resulting from the

court’s statements. Pena points out that the district court’s request prompted

Stanton’s motion to withdraw as counsel because of the conflict. Pena argues

that, although Stanton did not specify the complete nature of the conflict at that

time, he intimated to the district court that he was incapable of disclosing the

conflict in full. Subsequent proceedings revealed that Stanton held a portion of
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7 The government confirmed during oral argument that it has now indicted several of

Stanton’s clients, as well as Pena, for wrongdoing related to the SDVO monies.

8 Alternatively, according to the government, the district court said that it would grant

Pena full credit for acceptance of responsibility if he resolved the SDVO matter before entering

his plea. According to the court, it stated that Pena should resolve the civil SDVO matter

21

the disputed SDVO monies in his attorney trust account. Meanwhile, Pena

continued to be debriefed by the government regarding these same monies in

light of his perception that the court wanted the matter resolved prior to his

sentencing and the government’s apparent interest in this information. These

debriefings potentially exposed Stanton’s civil SDVO clients to criminal liability.7

The government argues that, even if the district court erred, Pena cannot

show any harm because: 1) Pena had already decided to plead guilty when the

court made the statement; 2) Pena’s plea colloquy demonstrates that his plea

was knowing and voluntary; and 3) the court withdrew the condition relating to

resolution of the “SDVO matter” soon after it made its statement to the parties.

The governmentfurther asserts thatthe SDVO matter and the instant cases are

completely unrelated, and thus any alleged conflict between Pena and Stanton

is specious.

3. Discussion

The Supreme Court recently emphasized that “[v]acatur of [a] plea is not

in order if the record shows no prejudice to [a defendant]’s decision to plead

guilty.” Davila, 2013 U.S. LEXIS 4541, at *8 (emphasis added). Thus, although

the primary focus of our prejudice analysis must be the period between the

district court’s participation andPena’s guilty pleas, our review is also “informed

by the entire record.” Dominguez Benitez, 542 U.S. at 83. The district court

indicated that it would not accept Pena’s pleas unless Pena also resolved the

SDVO matter; that statement amounts to a hypothetical agreement that the

court preferred.8 Just five days later, Pena pled guilty—a temporal proximity
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before his plea in the instant proceedings. These statements would constitute a plea bargain.

9 Although the government assessed the impact of the court’s condition under a

harmless-error standard, its arguments are still germane to our plain-error analysis. See

United States v. Olano, 507 U.S. 725, 734 (1993) (citations omitted) (clarifying that the third

prong of plain-error reviewSSthat the error must “affec[t] substantial rights”SS“is the same

language employed in [Federal Rule of Criminal Procedure] 52(a) [‘Harmless Error’], and in

most cases it means that the error must have been prejudicial: It must have affected the outcome of the district court proceedings.”); see also 28 Moore’s Federal Practice § 652.04[4], at

652-30 to -32 (Daniel R. Coquillette et al. eds., 3d ed. 2013) (citations omitted) (“The Olano

Court pointed outthat[whether obvious error ‘affect[s] substantial rights’] is exactly that same

standard applied in harmless error review under Rule 52(a)[.]”).

22

that supports a finding of prejudice. See Davila, 2013 U.S. LEXIS 4541, at *26

(contrasting a plea that follows “soon after” judicial participation with a threemonth delay). 

The government maintains that even if the district court impermissibly

participated inPena’s plea negotiations,that error did not affect Pena’s substantial rights, because he had already decided to plead guilty.9 As Pena notes,

however, plea negotiations were merely ongoing, and the parties had disclosed

no terms to the court. This distinction is crucial, as we have already discussed.

See Crowell, 60 F.3d at 204 (citation omitted). Stanton’s motion to withdraw,

moreover, asserted that“DefendantPena continues to wish to enter a plea under

the terms which were the subject of the general agreement of the parties prior

to the declaration of the Court setting out a resolution of the SDVO claims.”

That contemporaneous account indicates that there was no definite agreement

in advance of the district court’s participation. 

In Rodriguez, we specifically rejected the government’s argument that,

because the defendant had already negotiated a plea with the government before

the district court’s participation in plea negotiations, the court’s error did not

impactthe proceedings, because we knew the precise agreement that would have

resulted in the case. See Rodriguez, 197 F.3d at 160 n.15. We stated that, by
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making that argument,“the governmentignores what we do not knowSSwhether

[the defendant] would have entered the agreement at all absent the judge’s

involvement.” Id. We thus concluded that the district court’s statements

pressured the defendant to plead guilty, even though the statements did not

alter the terms ofthe previously negotiated agreement, because “Rule 11 applies

to all forms of participation.” Id. at 157-59, 160 n.15; see also Miles, 10 F.3d at

1141.

Even though the district courttold the parties thatit was withdrawing the

condition and that they should “disregard” it, the record evidences that the

“withdrawal” did not alter Pena’s perception of the court’s desired disposition.

Pena still thought that he needed to resolve the SDVO matter to the extent that

he could before entering his pleas. As we observed in Rodriguez:

Once the judge placed pressures on Rodriguez, their

impact could not be so readily alleviated. The clear

implication of the judge’s statements at the pretrial

hearing was that the judge desired a plea. It is reasonable to doubt that any amount of explanation from Rodriguez’s attorney could have cured the impression likely

left in Rodriguez’s mind that “refusal to accept the

judge’s preferred disposition would be punished.” 

Rodriguez, 197 F.3d at 160 (citations omitted); see also Miles, 10 F.3d at 1141.

The record also suggests that, by imposing and then quickly retracting a

unilateral condition,the district court unintentionally induced Pena—who might

have otherwise continued bargaining—to plead guilty quickly, lest the court

change its mind again. The pre-plea proceedings before the court, therefore,

illustrate one of the core concerns that Rule 11 was intended to combat, i.e., the

indeterminate effects ofthe court’s involvementin plea negotiations, even if only

in the defendant’s mind. See Miles, 10 F.3d at 1141 (citing Barrett, 982 F.2d at

194 (“By intervening to facilitate a plea, . . . the judge communicated to the
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10 Davila cites Miles with apparent favor. See Davila, 2013 U.S. LEXIS 4541,

at *15 n.2.

11 Again, the district court said to Pena:

I need to direct your attention to the duty of financial candor

section contained in both plea agreements in both of these

cases . . . . I am going to instruct my probation officer within ten

days of today to set up a meeting with you in which you are going

to disclose the totality of your financial dealings, who have you

given money to recently, say in the last year, that is out of the

ordinary. 

24

defendant that he desired a plea. He thereby raised the possibility, if only in the

defendant’s mind,that a refusalto acceptthe judge’s preferred disposition would

be punished.”)).10

Subsequent proceedings also illustrate the impact of the court’s condition

on Pena’s perception of the terms of his guilty pleas: He persisted in trying to

do something about the SDVO matter long after the district court had retracted

its plea condition. One of Pena’s pro se filings alleged that he had attempted to

include resolution of the SDVO matter in his plea agreements following the

court’s withdrawal of the condition, but the attorneys did not include that term.

Further, Pena’s communications with the probation officer indicate that Pena

interpreted the “duty of financial candor” provision in his plea agreementSS

which the district court highlighted during the plea hearingSSto include candor

with respect to the SDVO matter specifically. The district court’s emphasis on

this section of Pena’s plea agreement likely reaffirmed, in Pena’s mind, the

court’s desired disposition relating to the SDVO matter, even if that was not the

court’s actual intent.11 See Adams, 634 F.2d at 841 (citation omitted). Pena’s

decision to proceed without counsel during most of his debriefings and in his

communications with the probation officer demonstrates the far-reaching impact

ofthe district court’s involvement in the plea negotiations. We conclude that the
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25

participation affected Pena’s substantial rights, because it was “sufficient to

undermine confidence in the outcome of the proceeding.” Dominguez Benitez,

542 U.S. at 83 (citation omitted).

Finally, “we do not view the fourth prong [of plain-error review] as

automatic if the other three prongs are met.” United States v. Escalante-Reyes,

689 F.3d 415, 425 (5th Cir. 2012) (en banc) (citation omitted). Further, the

Supreme Court recently re-emphasized the inherent “screening criteria”

contained within the plain-error rule, under which a defendant’s failure to object

“may well count against”the grant of relief. See Henderson v. United States, 133

S. Ct. 1121, 1130 (2013).

Recognizing Pena’s high burden of demonstrating prejudice on plain-error

review, we nevertheless conclude that the district court’s participation in the

plea negotiations warrants reversal in this case. For all of the reasons we have

discussed, the district court’s error “seriously affected the fairness, integrity,

[and] public reputation of the judicial proceeding.” See Broussard, 669 F.3d at

553 (citation omitted). The district court’s participation precipitated Pena’s

efforts to “resolve the SDVO matter” through his pleas and debriefings, caused

him to proceed pro se in most subsequent proceedings before the district court,

and revealed a potential conflict of interest between Pena and Stanton and

undermines confidence in the resulting plea deal. In these ways, this case

presents those exceptional circumstances that warrant reversal on plain error.

Adams, 634 F.2d at 836 (concluding that the fourth prong was satisfied after

judicial participation in plea discussions). See United States v. Atkinson, 297

U.S. 157, 160 (1936) (“In exceptional circumstances, . . . appellate courts, in the

public interest, may . . . notice errors to which no exception has been taken[.]”);

see also United States v. Young, 470 U.S. 1, 15 (1985) (quoting United States v.
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Frady, 456 U.S. 152, 163 n.14 (1984)) (noting that the plain-error rule should be

employed when “a miscarriage of justice would otherwise result”).

We applaud the districtjudge’s recognition of his error when he attempted

to ameliorate the potential effects of his statements by communicating to the

parties,through his law clerk,thatthey were to disregard the condition. Despite

the best efforts of the trial judge, however, his comments had unintended

consequences. Thus, in light of our precedents, the appropriate remedy is

vacatur of Pena’s guilty pleas and sentences and reassignment of his cases to a

different judge on remand. See Daigle, 63 F.3d at 349 (“‘[I]n order to extend the

prophylactic scheme established by Rule 11,’ this case will be assigned to a

different judge on remand.” (quoting Miles, 10 F.3d at 1142)).

III. CONCLUSION

For the foregoing reasons, we VACATE Pena’s guilty pleas and sentences,

and we REMAND for further proceedings before a different district judge.