[DO NOT PUBLISH]

In the

United States Court of Appeals

For the Eleventh Circuit

____________________

No. 23-10061

Non-Argument Calendar

____________________

CARLOS MONTEMAYOR, 

a.k.a. Fox,

a.k.a. The Director,

a.k.a. Licenciado,

Petitioner-Appellant,

versus

UNITED STATES OF AMERICA, 

Respondent-Appellee.

____________________

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Appeal from the United States District Court

for the Northern District of Georgia

D.C. Docket No. 1:21-cv-03555-LMM

____________________

Before GRANT, ANDERSON and HULL, Circuit Judges. 

PER CURIAM:

Carlos Montemayor, a federal prisoner, appeals the district 

court’s denial of his counseled 28 U.S.C. § 2255 motion to vacate, 

correct, or set aside his conviction and sentence. In Montemayor’s 

underlying criminal case, Montemayor’s retained counsel was 

Richard Rice, who as an Assistant U.S. Attorney (“AUSA”) had 

participated in the investigation that led to Montemayor’s 

indictment. Because of that participation, the district court granted 

the government’s motion to disqualify Rice as Montemayor’s 

counsel. Later, the district court, at Montemayor’s request, 

appointed new counsel, Paul Cognac. Montemayor entered a 

guilty plea to six drug-related charges and was sentenced to 411

months of imprisonment. 

Montemayor’s § 2255 motion alleged, in relevant part, that 

his appointed counsel Cognac was constitutionally ineffective for 

failing to preserve for direct appeal the issue of Rice’s 

disqualification. The district court denied Montemayor’s § 2255 

motion, concluding he had not established ineffective counsel. 

After review, we affirm. 

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I. FACTUAL BACKGROUND

A. Indictment 

In 2004, the Drug Enforcement Agency (“DEA”) began a 

wiretap investigation of a drug trafficking organization led by 

Edwar Valencia-Gonzalez (“the Valencia investigation”). Through 

wiretap conversations, agents learned Montemayor was a source 

of Valencia’s cocaine in Atlanta, Georgia. 

As a result of the Valencia investigation, in 2009 a federal 

grand jury indicted Montemayor for: (1) conspiracy to possess with 

intent to distribute five kilograms or more of cocaine, in violation 

of 21 U.S.C. §§ 846, 841(b)(1)(A)(ii), and 18 U.S.C § 2 (“Count 

One”); (2) conspiracy to import five kilograms or more of cocaine, 

in violation of 21 U.S.C. §§ 963 and 960(b)(1)(B)(ii), and 18 U.S.C. 

§ 2 (“Count Two”); (3) three counts of possession with intent to 

distribute five or more kilograms of cocaine, in violation of § 841(a) 

& (b)(1)(A)(ii) (“Counts Four, Five, and Eight”); and (4) conspiracy 

to commit money laundering, in violation of 18 U.S.C. § 1956(h) 

(“Count Nine”). 

In 2010, Montemayor was arrested in Mexico, but not 

extradited to the United States until 2015. Initially, other attorneys

represented Montemayor. By 2016, Montemayor had retained 

former AUSA Rice, who had left the U.S. Attorney’s Office in 2008. 

While representing Montemayor, Rice filed a preliminary 

motion to suppress all communications and other evidence 

intercepted by all wiretaps. The motion to suppress argued, inter 

alia, that (1) the wiretaps failed to establish necessity, (2) the 

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wiretaps were used as an investigative tool, (3) information from 

illegal wiretaps was used to obtain the wiretaps, and (4) GPS 

information from target telephones was also unlawfully obtained. 

B. Motion to Disqualify Retained Counsel Rice

Pursuant to 18 U.S.C. § 207(a)(1), the government moved to 

disqualify Rice from representing Montemayor. Under that 

statute, a former AUSA is restricted from representing a criminal 

defendant “in connection with a particular matter . . . in which the 

[former AUSA] participated personally and substantially” during 

his time as a government attorney. 18 U.S.C. § 207(a)(1)(B). 

The government’s disqualification motion contended Rice, 

while an AUSA in the Narcotics Section, had led a wiretap 

investigation into a drug trafficking organization headed by Javier 

Alvarez-Lopez a.k.a. “Gotti” (“the Gotti investigation”). At the 

time, investigators believed that Gotti’s organization was doing 

business with the Valencia organization to which Montemayor 

belonged. As a result, in 2005, agents and AUSAs for both the Gotti 

and Valencia investigations coordinated and communicated with 

each other. During 2005, the AUSAs included in the “necessity” 

section of their wiretap applications information about both 

investigations and their connections to each other. And in wiretap 

applications for the Gotti investigation, Valencia was identified as 

a target. Likewise, Gotti was identified as a target in wiretap 

applications for the Valencia investigation. 

Further, in July and August 2005, Rice, assigned to the Gotti 

investigation, assisted his counterpart in the Valencia investigation, 

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then-AUSA John Horn, by working on three pen register 

applications for call and cell site data for certain phones when Horn 

was unavailable. Rice certified that he had discussed the 

applications with an investigating agent in the Valencia 

investigation. From the pen registers, agents in the Valencia 

investigation received information about intercepted calls in which 

Montemayor discussed drug trafficking activities with an 

intermediary between the Gotti and Valencia drug trafficking 

organizations. 

Ultimately, investigators concluded that, while the two drug 

trafficking organizations sometimes shared sources of supply in 

Mexico and communicated with each other, they largely operated 

independently, and Montemayor’s indictment did not cover the 

Gotti organization. That said, the government represented that it 

might introduce the recorded calls from the Valencia investigation 

as evidence against Montemayor at trial. 

C. Attachments to Disqualification Motion

The government attached to its disqualification motion 

copies of (1) wiretap applications and affidavits from June through 

November 2005 associated with the Valencia investigation,

(2) wiretap applications and affidavits from May through 

September 2005 associated with the Gotti investigation, and (3) the 

pen register applications then-AUSA Rice handled for AUSA Horn

in July and August 2005. 

As just one example, in a July 15, 2005 wiretap application 

Horn submitted as part of the Valencia investigation, Gotti was 

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identified as a target. The background section of DEA agent Renita 

Foster’s affidavit supporting the application, described the 

investigations into the Valencia and Gotti organizations. Agent 

Foster averred that the Valencia and Gotti organizations were cells 

of a Mexican drug trafficking organization that each appeared to 

have their own sources of supply and distribution challenges, and 

stated: 

However, conversations intercepted on Title III 

wiretaps to date show that VALENCIA-GONZALEZ 

communicates with GOTTI regarding the 

distribution of illegal drugs, and they appear to use 

some of the same resources, such as warehouses to 

unload truckloads of drugs and stash houses to store 

drugs and/or currency. The wiretaps also show that 

several Target Subjects, such as JOHN DOE, a.k.a.

“ULYSSES,” JOHN DOE, a.k.a. “OSCAR,” and FNU 

LNU, a.k.a. “GORDO,” have participated in illegal 

activities for both cells. Based on the investigation to 

date, it appears that VALENCIA-GONZALEZ and 

GOTTI have used at least one common source of 

supply, although they also use different sources of 

supply as well. In addition, I believe that a loose 

connection exists between VALENCIA-GONZALEZ 

and GOTTI based on the conversations and 

overlapping co-conspirators. Nevertheless, the 

investigation indicates that VALENCIA-GONZALEZ 

are [sic] operating independently. During the next 30 

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days, agents hope to explore more fully the extent of 

their relationship.

Similar descriptions of, and references to, the Valencia 

organization were included in affidavits supporting wiretap 

applications submitted by Rice for the Gotti investigation. 

The “necessity” section of DEA agent Foster’s Valenciainvestigation affidavit stated the following about the Gotti 

investigation:

In addition to the residences identified in this 

investigation, agents participating in the wiretap 

investigation of FNU LNU, a.k.a. “GOTTI,” and his 

drug distribution organization have identified four 

other locations associated with that cell . . . . Agents 

in Enforcement Group I continue to evaluate the 

feasibility of performing searches of these locations. 

However, even if searches are performed, I believe 

that the evidence obtained would be more useful in 

prosecuting GOTTI and members of his drug 

distribution organization. As stated earlier, while 

there appears to be a relationship between GOTTI 

and EDWAR VALENCIA-GONZALEZ, they use 

different sources of supply and distribution networks. 

Consequently, searches of these locations likely 

would be of only minimal assistance in the 

investigation of the VALENCIA-GONZALEZ 

organization.

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Agent Foster’s affidavit further stated about the Gotti organization:

As noted earlier, the two investigations have not 

conclusively identified the nature of this relationship 

[between the Valencia and Gotti organizations], but 

at a minimum it appears that VALENCIAGONZALEZ communicates with the manager of the 

other cell, FNU LNU, a.k.a. “GOTTI,” and they use 

some common resources, including warehouses and 

stash houses. There also appears to be at least one 

individual, JOHN DOE, a.k.a. “ULYSSES,” who has 

performed services for both cells. Notwithstanding 

these commonalities, it also appears that VALENCIAGONZELEZ and GOTTI use different sources of 

supply to obtain their drugs, and they also rely upon 

different distribution chains. Under these 

circumstances, although the wiretap investigation 

focusing on GOTTI may yield intercepted 

conversations with VALENCIA-GONZALEZ and, 

perhaps, other members of VALENCIAGONZALEZ’s organization, I do not believe that the 

conversations intercepted pursuant to the GOTTI 

investigation will yield evidence showing 

VALENCIA-GONZALEZ’s sources of supply, 

distributors, and methods of laundering his drug 

proceeds. Consequently, I believe that the 

interception of Target Telephones #1-4 is necessary 

to achieve the objectives of this investigation.

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Of the three pen register applications attached to the 

government’s disqualification motion, one, dated July 27, 2005, 

was prepared by Horn, but signed and submitted on Horn’s behalf 

by then-AUSA Rice. Another, dated August 4, 2005, seeking 

information on a telephone used by Valencia-Gonzalez, was 

prepared and signed by then-AUSA Rice, but was not presented to 

the district court. For both of these applications, Rice signed a 

declaration under penalty of perjury stating that he had discussed 

the applications with DEA agents involved in the Valencia 

investigation. 

The third pen register application, dated July 28, 2005, was 

fully prepared, signed, and submitted by then-AUSA Rice, and was 

authorized by the court. In that July 28 application, Rice stated that 

based on the Valencia investigation to date, it was believed the user 

of the target telephone, referred to as Cache, had used and 

continued to use the target telephone “to facilitate the receipt and 

distribution of illegal drugs and financial proceeds arising from 

such unlawful drug trafficking activity.” Rice further stated that 

pursuant to a court-authorized wiretap, agents had “intercepted 

calls in which CACHE discussed the distribution of illegal drugs 

and the collection of drug proceeds.” 

Rice certified that there were reasonable grounds to believe 

the requested records and information were relevant and material 

to the DEA’s ongoing criminal investigation of the Valencia drug 

trafficking organization and would assist “agents in identifying both 

co-conspirators in the drug trafficking activity and locations used 

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by these persons in connection with such activity.” Rice also 

declared under penalty of perjury that he had discussed the 

application with DEA agent Renita Foster, the same agent involved 

in Horn’s wiretap applications. 

Montemayor opposed the government’s disqualification 

motion, contending the two investigations were not related and 

did not coordinate prosecution strategy. Montemayor conceded, 

however, that then-AUSA Rice had “signed one Pen App on behalf 

of AUSA Horn and then prepared one Pen App and Order for 

agents conducting the Valencia investigation while AUSA Horn was 

on vacation,” but maintained that these activities did not 

“constitute personal and substantial involvement” required for 

disqualification under § 207(a). (Emphasis added.) Montemayor 

also attached copies of the pen register requests Rice handled while 

Horn was on vacation. 

D. Parties Waive Evidentiary Hearing and Agree to Submit 

Declarations

Initially, a magistrate judge determined that Montemayor 

was entitled to an evidentiary hearing on the government’s 

disqualification motion. The magistrate judge set the evidentiary 

hearing for January 2017. However, the parties then notified the 

magistrate judge that they agreed additional evidence, necessary 

for the court to rule on the disqualification motion, could be 

presented by sworn declarations of Horn and Rice. The magistrate 

judge allowed the parties to proceed in this manner and cancelled 

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the evidentiary hearing. The parties then submitted dueling 

declarations from Horn and Rice. 

In their declarations, Horn and Rice did not agree on the 

extent to which the Gotti and Valencia investigations overlapped 

and shared information and the extent to which the two AUSAs 

conferred and coordinated with each other. We do not include all 

of Horn’s allegations, but provide a brief overview of Horn’s 

description of the extensive overlap and coordination between his 

Valencia investigation and Rice’s Gotti investigation. 

E. AUSA Horn’s Declaration

Consistent with the wiretap applications attached to the 

government’s motion, Horn’s declaration stated that between 

April and July 2005, investigators learned through phone data and 

wiretaps that Gotti and Valencia frequently communicated with 

each other, bought and sold drugs from each other, appeared to 

share some of the same warehouses and stash houses to store drugs 

and currency, and sometimes purchased drugs from a common 

source of supply. There also appeared to be one individual, called 

Ulysses, whom agents initially believed participated in both the 

Gotti and the Valencia organizations. 

According to Horn, this overlap between the Gotti and 

Valencia investigations caused some tension and required the 

agents and AUSAs within the two investigative groups to 

communicate and coordinate with each other on an ongoing basis. 

The “fruits of this coordination are memorialized in the facts and 

necessity sections of the agents’ wiretap affidavits, including the 

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July 27, 2005 wiretap affidavit submitted by Mr. Rice in the Gotti 

investigation.” Through the fall of 2005, Gotti and Valencia 

continued to have interactions with each other that had “to be 

analyzed and discussed in the ongoing wiretap affidavits’ necessity 

sections” of both investigations and the “wiretap materials 

submitted in each investigation therefore continued to reference 

the other investigation.” 

Horn also said that as an AUSA in the Narcotics Section, he 

attended mandatory weekly meetings with other AUSAs, including 

Rice, at which he “openly shared” information about the Valencia 

investigation. Horn also recalled: (1) speaking and exchanging 

information with Rice about their respective investigations “in 

connection with resolving the relationship between Valencia and 

Gotti”; (2) discussing “the facts of [their] respective investigations . 

. . on multiple occasions”; (3) “coordinat[ing] with each other in the 

drafting and submitting of the wiretap pleadings described in the 

government’s Motion to Disqualify”; and (4) at least one meeting 

with Rice and DEA agents from both the Gotti and Valencia 

investigations to discussthe tensions between the two investigative 

groups caused by overlaps in the two investigations. Finally, Horn 

explained that he would have “review[ed] with [Rice] the language 

to be included in the necessity sections of the wiretaps to ensure 

that they were accurate and consistent,” before including any 

information about the Gotti investigation in his wiretap 

applications for the Valencia investigation. 

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F. Rice’s Declaration

Next, we outline what Rice’s declaration said about his 

interactions with Horn and the Valencia investigation. Because 

Rice’s admissions alone show his substantial and personal 

involvement in the Valencia investigation, we recount them also 

in detail.

According to Rice, he was generally aware of the Valencia 

investigation. For a time, the DEA case agent for Rice’s Gotti 

investigation suspected that an individual named Ulysses was 

involved in both the Gotti organization and the Valencia 

organization. It later turned out they were separate individuals 

with the same name. 

But while Rice was involved as an AUSA, the two 

investigations needed to be identified in wiretap applications and 

affidavits for each investigation, including in the “necessity” and 

“prior applications” sections of wiretap affidavits. As a result, 

AUSA Horn and AUSA Rice each prepared and provided to the 

other text about their respective investigations to be “cut and 

pasted” into wiretap applications and affidavits. Rice told the DEA 

case agent for the Gotti investigation to “stay away from” the 

Valencia investigation, and from that point on, Rice’s only 

discussions about the Valencia investigation were to confirm that 

the Gotti investigation was steering clear of the Valencia 

investigation. 

Rice recalled one joint meeting of the two groups of 

investigators, and possibly Horn, “to discuss and ensure there was 

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no overlapping investigation.” However, Rice left the meeting 

before any substantive discussions of the two investigations began. 

Rice admitted that he attended most weekly meetings of the DEA 

agents involved in his Gotti investigation and weekly meetings of 

AUSAs in the Drug Section. Yet Rice did not recall having any 

substantive discussions about the Valencia investigation with DEA 

agents or AUSA Horn. 

Rice acknowledged, however, that in late summer 2005, 

AUSA Horn went on vacation. Prior to leaving, Horn asked Rice 

to prepare pen register applications for the Valencia investigation, 

which Rice called “Pens Apps,” that would be needed during 

Horn’s absence, and Rice agreed. Rice prepared two pen register 

applications while Horn was absent. Rice sent the DEA agents 

involved in the Valencia investigation his template for pen register 

applications, the DEA agents for the Valencia investigation used 

the template and drafted a paragraph of “particularized language”

stating the factual basis justifying obtaining the phone data, and 

then the DEA agents submitted the two pen register applications 

to Rice, who revised them, as needed. Rice could not recall what 

revisions, if any, he made to the particularized language in these 

two pen register applications for the Valencia investigation. 

For the July 27, 2005 pen register application, Rice certified 

that he had discussed the application with the investigating agent. 

Rice said that during his process of preparing a pen register 

application, his “discussions with the agent who sought the Pen 

App would be limited to the particularized paragraph providing the 

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factual basis justifying obtaining the information pursuant to the 

order.” Consistent with this process, Rice did not discuss the 

Valencia investigation with the DEA agents “other than reviewing 

the particularized paragraph in the Pen App and Order.” 

One of the pen register applications Rice prepared and 

signed while Horn was on vacation was taken by the DEA agents 

in the Valencia investigation to a magistrate judge for review and 

signature. The other pen register application was not, “although 

AUSA Horn prepared a Pen App for the telephone that was the 

subject of the second Pen App after AUSA Horn returned.” Apart 

from this activity, Rice denied participating in or assisting the 

Valencia investigation and the criminal cases that resulted from it. 

Rice maintained that he had no knowledge of the defendants 

in the criminal cases resulting from the Valencia investigation until 

he became Montemayor’s defense counsel. 

G. Montemayor Waives Conflict-Free Counsel

While the disqualification motion was pending, the 

magistrate judge held a Garcia hearing, at which Montemayor 

waived any potential conflict of interest Rice had due to an overlap 

between the Gotti and Valencia investigations.1 By this time, 

1 United States v. Garcia, 517 F.2d 272 (5th Cir. 1975), abrogated on other grounds 

by Flanagan v. United States, 465 U.S. 259 (1984). “Garcia provides that, in the 

case of a potential conflict of interest, the court should conduct an inquiry, 

akin to a plea colloquy under Federal Rule of Criminal Procedure 11, to 

determine whether a defendant wishes to waive the conflict.” United States v. 

Valois, 915 F.3d 717, 727 (11th Cir. 2019).

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another attorney, W. Coleman Sylvan, had joined Rice as retained 

co-counsel for Montemayor, and Montemayor had obtained 

independent advice from Sylvan before entering the waiver. 

Montemayor signed a written waiver, and the magistrate judge 

found the waiver was knowingly, voluntarily, and intelligently

made. 

H. Magistrate Judge Disqualifies Rice

In a 45-page order, the magistrate judge acknowledged that

Montemayor’s waiver of conflict-free counsel gave rise to a 

presumption in favor of counsel of choice. But the magistrate 

judge found that the government had carried its burden to show 

retained counsel Rice must be disqualified under § 207(a)(1). The 

magistrate judge initially credited Horn’s recollection over Rice’s 

as to “how he and Mr. Rice satisfied their responsibilities, that is, 

before including any information about the other AUSA’s 

investigation” in wiretap applications and affidavits and that Horn 

and Rice “discussed the information to be included . . . in order to 

draft the applications and affidavits.” The magistrate judge found 

that, although Rice was not the lead AUSA in the Valencia 

investigation and did not participate in every decision made about 

that investigation or prosecution, “he did participate sufficiently to 

trigger application of § 207(a)(1).” 

Alternatively, the magistrate judge found that, “even if the 

court relies on Mr. Rice’s statement as to how the information was 

exchanged for inclusion in the wiretap affidavits, his involvement 

in the Valencia . . . investigation is just as, if not more, personal and 

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substantial.” After analyzing Rice’s declaration, the magistrate 

judge concluded it alone was enough to establish that Rice’s 

participation in the Valencia investigation was “substantial and 

personal,” as he had conversations with the investigating agents, 

reviewed the information available for both investigations, 

determined what information was required to satisfy the necessity 

finding, crafted that language, and sent it to Horn for inclusion in 

the Valencia wiretap affidavits. 

The magistrate judge also found that, even if there was no 

actual conflict of interest, there was an appearance of a conflict of 

interest because Rice, then representing Montemayor, had “filed a 

motion to suppress the wiretap authorizations, attacking the 

necessity for the wiretaps, which relied in part on the language that 

[Rice] claims he supplied for the very same wiretap affidavits.” 

Thus, the magistrate judge concluded that the court would reach 

the same conclusion whether Rice’s participation was as described 

by Rice or Horn. 

I. District Court Affirms Disqualification Order

The district court overruled Montemayor’s objections and 

affirmed the magistrate judge’s order disqualifying Rice. The 

district court agreed with the magistrate judge’s findings about 

Rice’s involvement in the Valencia investigation based on Horn’s 

declaration. 

The district court also agreed with the magistrate judge that, 

“[e]ven if the Court relies on Mr. Rice’s statements describing his 

claimed limited involvement” Rice’s admitted participation in the 

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Valencia investigation—preparing text about the Gotti 

investigation for Horn to include in his wiretap applications and 

affidavits and working with agents at Horn’srequest to prepare and 

submit pen register and cell site requests for the Valencia 

investigation—was substantial and personal. The district court 

further found that Rice’s sworn certifications in support of the pen 

register requests “severely undercut[]” his later claim, in response 

to the government’s motion to disqualify, that he had not received 

any information about the Valencia organization beyond what was 

included in the wiretap application and affidavit. The district court 

concluded that Rice’s involvement in the Valencia wiretap 

applications and pen register requests constituted personal and 

substantial participation in the Valencia investigation. Thus, the 

district court found that Rice was properly disqualified under 

§ 207(a)(1), and it affirmed the magistrate judge’s order and 

disqualified Rice from the case. 

J. Montemayor’s Unconditional Guilty Plea 

After Rice’s disqualification, Montemayor filed a pro se

motion to “disqualify” his retained co-counsel Sylvan and 

requested appointed counsel. At a hearing, Montemayor 

confirmed that he wished to terminate Sylvan as his retained 

attorney and he did not have funds to retain new counsel. On 

December 7, 2017, the district court appointed attorney Cognac to 

represent Montemayor. 

Almost a year later, in November 2018, Montemayor 

entered a non-negotiated, unconditional guilty plea. During the 

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plea hearing, the district court informed Montemayor (1) of his 

right to proceed to trial, (2) of the rights he was waiving by pleading 

guilty, and (3) that after pleading guilty, the only rights he would 

keep were “the right to have a lawyer represent you, advise you 

about the case, argue on your behalf at sentencing, and to appeal 

any legal defect in your plea or your sentence.” 

The district court confirmed: (1) the government had 

offered Montemayor a plea bargain, which Montemayor discussed 

with his attorney Cognac; (2) Montemayor had decided not to 

accept the government’s offer; and (3) Montemayor still wanted to 

plead guilty. After a colloquy, Montemayor admitted guilt to all 

six counts against him in the indictment. The district court found 

Montemayor’s plea was knowingly, voluntarily, and intelligently 

made on the advice of competent counsel. 

K. Sentencing and Motion to Withdraw Guilty Plea

At a May 16, 2019 sentencing hearing, the district court 

imposed terms of 411 months on Counts One, Two, Four, Five and 

Eight and a term of 240 months on Count Nine, all to run 

concurrently. The sentencing was held open for resolution of the 

amount of forfeiture. Approximately two weeks later, new 

retained counsel, Stephen Reba, entered an appearance as counsel 

for Montemayor, and Cognac filed a motion to withdraw, which 

the district court granted. 

Montemayor, through retained counsel Reba, moved to 

withdraw his guilty plea. Montemayor argued that Cognac had 

given him constitutionally deficient advice to reject the 

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government’s plea deal of approximately 25 years in prison and to 

enter a non-negotiated plea that Cognac predicted would likely 

result in a sentence of 10 to 15 years. The district court denied 

Montemayor’s motion to withdraw his guilty plea. On August 7, 

2019, the district court entered the final judgment of conviction and 

sentence. 

L. Direct Appeal

On direct appeal, Montemayor challenged, among other 

things, the order disqualifying Rice. See United States v. Montemayor, 

815 F. App’x 406, 407 (11th Cir. 2020). Montemayor argued the 

district court committed a fundamental error when it disqualified 

Rice without holding an evidentiary hearing. Id. at 408. This Court 

concluded that by entering an unconditional guilty plea that was 

knowing and voluntary, Montemayor had waived his challenge to 

Rice’s disqualification and affirmed Montemayor’s convictions. Id.

at 409-10.2 

II. SECTION 2255 MOTION

In August 2021, Montemayor filed this counseled § 2255 

motion. In Ground One, Montemayor claimed that during plea 

proceedings counsel Cognac was ineffective for failing to raise and 

preserve properly for direct appeal the issue of Rice’s 

2 On direct appeal, Montemayor challenged the district court’s forfeiture 

order, but not his 411-month prison sentence. See Montemayor, 815 F. App’x 

at 407.

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disqualification.3 Montemayor asserted Cognac’s ineffective 

assistance amounted to structural error. Montemayor pointed out 

that he had waived any conflict that Rice might have had, giving 

rise to a presumption in favor of Rice representing him. 

Montemayor contended the district court had reversibly erred in 

concluding that the government had overcome the presumption 

by demonstrating an actual conflict of interest or a serious potential 

conflict of interest. 

A magistrate judge issued a report and recommendation 

(“R&R”), recommending that Montemayor’s § 2255 motion be 

denied. As to Montemayor’s ineffective counsel claim regarding 

disqualification of Rice, the R&R concluded Montemayor failed to 

establish that his counsel Cognac was ineffective under the twopronged test of Strickland v. Washington, 466 U.S. 668 (1984). On 

the R&R record, the magistrate judge concluded any basis for 

challenging on appeal the district court’s disqualification of Rice 

was “patently meritless.” Thus, counsel Cognac’s performance 

was not ineffective and did not prejudice Montemayor in any 

event. In this regard, the magistrate judge first pointed out that 

Montemayor could have preserved the disqualification issue only 

by either entering a conditional plea or proceeding to trial. But 

Montemayor had proffered no evidence that the government 

3 Montemayor’s § 2255 motion raised two other ineffective-assistance-ofcounsel claims that we do not discuss because they fall outside the scope of 

the certificate of appealability. See McKay v. United States, 657 F.3d 1190, 1195 

(11th Cir. 2011). 

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would have agreed to (and the district court would have accepted) 

a conditional plea or that Montemayor was prepared to go to trial. 

Alternatively, the magistrate judge concluded there was “no 

reasonable probability” that on direct appeal Montemayor would 

have prevailed on the disqualification issue. In that regard, the 

magistrate judge determined that any appeal arguing, as 

Montemayor did in his § 2255 motion, that the district court erred 

by weighing the credibility of Horn and Rice without holding an 

evidentiary hearing would be dismissed under the invited error 

doctrine because Montemayor had waived the hearing and agreed 

to proceed by sworn declarations. 

The magistrate judge determined that “even without 

weighing the relative credibility of” the two competing 

declarations, the rest of the record, including “sworn documents 

that Rice himself certified and submitted to the Court” plainly 

showed that the Gotti and Valencia investigations “overlapped and 

that Rice had personal and substantial involvement and knowledge 

regarding both (including when he stepped into Horn’s role in the 

Valencia . . . investigation while Horn was on vacation).” In short, 

the magistrate judge concluded “Montemayor’s counsel could not 

have been ineffective for having ‘failed’ to preserve that meritless 

issue for appeal.” 

Over Montemayor’s objections, the district court adopted 

the R&R and denied Montemayor’s § 2255 motion. Among other 

things, the district court agreed with the magistrate judge that even 

if counsel Cognac had properly preserved the issue for direct 

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appeal: (1) “the Eleventh Circuit would not have granted relief 

because Movant invited the error [of making credibility 

determinations without a hearing] by agreeing to (and later failing 

to object to) the use of the declarations”; (2) “evidence beyond the 

declarations showed that Rice had been involved in an 

investigation of a drug trafficking organization whose operations 

overlapped with the organization with which Movant was 

associated”; and (3) as a result, there was “no reasonable probability 

that Movant would have prevailed on that issue before the 

Eleventh Circuit.” 

III. STANDARD OF REVIEW

In considering a district court’s denial of a § 2255 motion, we 

review findings of fact for clear error and questions of law de novo. 

McKay v. United States, 657 F.3d 1190, 1195 (11th Cir. 2011). 

Ineffective-assistance-of-counsel claims present mixed questions of 

law and fact that we review de novo. Osley v. United States, 751 F.3d 

1214, 1222 (11th Cir. 2014). 

IV. DISCUSSION

A. Certificate of Appealability

This Court granted a certificate of appealability (“COA”) as 

to “[w]hether the district court erred in determining that 

Montemayor could not establish prejudice, as to his ineffective 

assistance claim, based on his counsels’ failure to preserve the issue 

of his predecessor counsel’s disqualification.” 

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B. General Principles: Ineffective Assistance

A movant under § 2255 bears the burden to prove he is 

entitled to relief. Beeman v. United States, 871 F.3d 1215, 1222 (11th 

Cir. 2017). To prevail on an ineffective-assistance-of-counsel claim, 

a § 2255 movant must show both that: (1) his counsel’s performance 

was deficient, in that it fell below an objective standard of 

reasonableness; and (2) that he suffered prejudice as a result of that 

deficient performance. Strickland v. Washington, 466 U.S. 668, 687-

88 (1984). Because both prongs must be met, a court need not 

determine whether counsel’s performance was deficient if the 

movant failed to show sufficient prejudice. Id. at 697. Generally, 

prejudice occurs when there is a “reasonable probability that, but 

for counsel’s unprofessional errors, the result of the proceeding 

would have been different.” Id. at 694. 

When a movant asserts “the unusual claim” that his counsel

ultimately failed to preserve for appeal an issue that was raised and 

rejected in the trial court, “the appropriate prejudice inquiry asks 

whether there is a reasonable likelihood of a more favorable 

outcome on appeal had the claim been preserved.” Davis v. Sec’y 

for Dep’t of Corr., 341 F.3d 1310, 1316 (11th Cir. 2003) (involving trial 

counsel’s failure to renew a Batson objection at the conclusion of 

voir dire). In other words, in the “peculiar circumstances” where 

“the only effect of trial counsel’s negligence” is on the defendant’s 

appeal, we “must consider how [the movant] would have fared on 

[direct] appeal had counsel preserved [the neglected] claim for 

review.” Id. at 1315, 1316. 

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We recognize that the government contends that to 

demonstrate prejudice, Montemayor must show a reasonable 

probability that, but for counsel Cognac’s errors, Montemayor 

would not have pled guilty and would have insisted on going to 

trial. That is the prejudice standard generally applicable to 

ineffective-assistance-of-counsel claims in the guilty plea context. 

See Hill v. Lockhart, 474 U.S. 52, 59 (1985). Montemayor cannot 

satisfy this prejudice standard articulated in Hill, as he did not aver 

that he would have insisted on going to trial had Cognac performed 

differently.

Nonetheless, the gravamen of Montemayor’s ineffectiveassistance-of-counsel claim is that counsel Cognac’s alleged error 

affected his direct appeal, i.e., Cognac failed to advise him to enter 

a conditional plea that preserved his right to appeal the 

disqualification order. Thus, the more appropriate prejudice 

standard for Montemayor’s particular claim here is the one 

articulated in Davis, which is whether there is a reasonable 

likelihood of a more favorable outcome on direct appeal if the 

claim had been preserved See Purvis v. Crosby, 451 F.3d 734, 739 

(11th Cir. 2006). 

C. Montemayor’s Ineffective Counsel Claim

Here, in the § 2255 proceedings, the district court did not err 

in determining that Montemayor could not establish prejudice. 

Montemayor has not shown a reasonable likelihood that he would 

have succeeded on the disqualification issue on direct appeal had it 

been properly preserved. That is because the magistrate judge in 

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Montemayor’s underlying criminal case correctly concluded Rice 

was prohibited from representing Montemayor under § 207(a), and 

the district court properly affirmed that order.

A criminal defendant has the Sixth Amendment right to 

counsel, which includes the right to counsel of his choice. United 

States v. Gonzalez-Lopez, 548 U.S. 140, 144 (2006). While a 

defendant has “a presumptive right to counsel of choice,” the right 

“is not absolute” because in addition to the defendant’s right to an 

effective advocate, there is “the judiciary’s interest in ensuring and 

maintaining the integrity of our judicial system.” United States v. 

Campbell, 491 F.3d 1306, 1310 (11th Cir. 2007) (quotation marks 

omitted). To overcome the presumption in favor of a defendant’s 

counsel of choice where the defendant has waived potential 

conflicts, the government must show either an “actual conflict . . . 

[or] a serious potential for conflict.” Wheat v. United States, 486 U.S. 

153, 164 (1988). 

In addition, a former AUSA is restricted from representing a 

criminal defendant “in connection with a particular matter . . . in 

which the [former AUSA] participated personally and 

substantially” during their time as a government attorney. See 18 

U.S.C. § 207(a)(1)(B). 

Here, in Montemayor’s underlying criminal case, the 

magistrate judge found, and the district court affirmed, that Rice, 

while an AUSA, “personally and substantially” participated in the 

Valencia investigation even when Rice’s declaration was fully 

credited. There is no clear error in this finding. In particular, Rice 

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admitted participating in the Valencia investigation by: 

(1) preparing text about his Gotti investigation that Horn used in 

his wiretap affidavits and applications, including in the “necessity” 

sections of the affidavits; and (2) preparing, reviewing, revising, and 

signing two pen register requests for call and cell site data for target 

phones. Moreover, in preparing the pen register requests, Rice 

conceded that he discussed with an investigating DEA agent the 

“particularized paragraph” containing the factual basis for 

obtaining the phone data. 

The magistrate judge also properly concluded that Rice’s 

representation of Montemayor presented at least the appearance of 

a conflict of interest, if not an actual conflict of interest, given that 

Rice had filed on Montemayor’s behalf a motion to suppress all 

wiretap evidence. As the magistrate judge pointed out, Rice’s 

motion to suppress explicitly attacked the necessity for the 

wiretaps, and Rice admitted preparing some of the language in the 

“necessity” sections of those wiretap applications. Further, the 

government contemplated using at trial recorded conversations

intercepted pursuant to the Valencia investigation wiretaps, and at 

least one of those recorded conversations was of Montemayor 

discussing drug trafficking activities with an intermediary between 

the Valencia and Gotti organizations. In other words, at the time 

of the disqualification motion, it was already apparent that Rice, on 

behalf of Montemayor, was now arguing that the wiretap 

applications and pen register requests he had helped prepare while 

an AUSA were unlawful and that evidence obtained from them 

could not be used against Montemayor. 

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In short, Rice’s own admissions in his declaration about his 

involvement in the Valencia investigation, along with the 

undisputed portions of the record, such as the wiretap applications 

and pen register requests, were sufficient to overcome the 

presumption in favor of Rice representing Montemayor. Under 

these circumstances, we readily conclude Montemayor would not 

have prevailed on this disqualification issue on direct appeal, even 

if appointed counsel Cognac had advised Montemayor to enter a 

conditional plea that properly preserved it.

Montemayor argues that he would have prevailed on the 

disqualification issue on direct appeal because the magistrate judge 

improperly credited Horn’s declaration without holding an 

evidentiary hearing, thereby shifting the burden from the 

government to overcome the presumption in favor of Rice’s 

representation. According to Montemayor, the magistrate judge 

was “unable to make credibility determinations” in ruling on the 

disqualification motion because the government, which had the 

burden, declined an evidentiary hearing. 

However, Montemayor does not dispute that, after the 

magistrate judge scheduled an evidentiary hearing on the 

disqualification motion, he and the government agreed to forgo an 

evidentiary hearing and asked the magistrate judge instead to 

consider the parties’ declarations in determining whether the 

government had overcome the presumption in favor of Rice’s 

representation. In other words, Montemayor invited any alleged 

error by the magistrate judge in making credibility findings and 

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resolving factual disputes without holding an evidentiary hearing. 

Accordingly, on direct appeal, this Court could have affirmed the 

magistrate judge’s disqualification of Rice without addressing the 

merits of Montemayor’s arguments based on the invited error

doctrine. See United States v. Brannan, 562 F.3d 1300, 1306 (11th Cir. 

2009) (stating that this Court is “precluded . . . from reviewing an 

issue raised on appeal if it has been waived through the doctrine of 

invited error”).4 

In any event, Montemayor’s argument ignores the 

magistrate judge’s alternative ruling, affirmed by the district court, 

that Rice’s own declaration showed he had personally and 

substantially participated in the Valencia investigation and 

presented a serious potential conflict of interest. Therefore, any 

alleged error—arising from crediting Horn’s declaration over 

Rice’s declaration without holding a hearing—would not have 

prevented this Court from affirming the disqualification order on 

this independent, alternative ground. See United States v. Campbell, 

26 F.4th 860, 879 (11th Cir. 2022) (en banc) (explaining that despite 

4 Nothing herein should imply that the magistrate judge or the district court 

was required to hold an evidentiary hearing and could not accept the parties’ 

agreement to proceed by written declarations. The fact that any alleged error 

was invited removes any need to address that issue. Further, we note that 

there may have been little for Montemayor to gain from an evidentiary 

hearing, at which the government could have brought out more detailed 

information about Rice’s involvement in, and knowledge of, the Valencia 

investigation than was covered by his declaration. For example, the 

government not only could have cross-examined Rice but also called DEA 

agents who had worked with Rice on both investigations.

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an error in the district court’s analysis, this Court may affirm a 

district court’s “ultimately correct” ruling on any ground 

supported by the law and the record); United States v. Maher, 955

F.3d 880, 885 (11th Cir. 2020) (“To obtain reversal of a district court 

judgment that is based on multiple, independent grounds, [an 

appellant] must convince us that every stated ground for the 

judgment against him is incorrect.” (quotation marks omitted)). 

Montemayor argues that on direct appeal he nonetheless 

would have prevailed because Rice’s disqualification was 

“structural error” not subject to harmless error analysis. It is true 

that the erroneous deprivation of a defendant’s right to counsel of 

his choice is structural error not subject to review for harmlessness. 

Gonzalez-Lopez, 548 U.S. at 148-50. But in Montemayor’s case, the 

decision to disqualify Rice was correct for the reasons already 

discussed and there was no erroneous deprivation of 

Montemayor’s Sixth Amendment right to counsel of choice. 

Because on direct appeal this Court would have affirmed 

Rice’s disqualification had Cognac preserved the issue for review, 

Montemayor cannot show prejudice under Strickland. See Davis, 

341 F.3d at 1316. 

V. CONCLUSION

The district court did not err in determining that 

Montemayor could not establish prejudice as to his ineffective 

assistance claim based on his counsel’s failure to preserve the issue 

of former retained counsel’s disqualification. For this reason, we 

affirm the district court’s denial of Montemayor’s § 2255 motion.

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AFFIRMED.

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