Carlos Montemayor v. USA

[DO NOT PUBLISH]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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2 Opinion of the Court 23-10061
Appeal from the United States District Court
for the Northern District of Georgia
D.C. Docket No. 1:21-cv-03555-LMM
____________________
Before G RANT, ANDERSON and H ULL , 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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23-10061 Opinion of the Court 3
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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4 Opinion of the Court 23-10061
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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23-10061 Opinion of the Court 5
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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6 Opinion of the Court 23-10061
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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23-10061 Opinion of the Court 7
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 Valencia-
investigation 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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8 Opinion of the Court 23-10061
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 VALENCIA-
GONZALEZ 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 VALENCIA-
GONZELEZ 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 VALENCIA-
GONZALEZ’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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23-10061 Opinion of the Court 9
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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10 Opinion of the Court 23-10061
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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23-10061 Opinion of the Court 11
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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12 Opinion of the Court 23-10061
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 discuss the 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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14 Opinion of the Court 23-10061
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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23-10061 Opinion of the Court 15
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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23-10061 Opinion of the Court 17
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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18 Opinion of the Court 23-10061
Valencia investigation—preparing text about the Gotti
investigation for Horn to include in his wiretap applications and
affidavits and working with agents at Horn’s request 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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23-10061 Opinion of the Court 19
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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23-10061 Opinion of the Court 21
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 two-
pronged 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-of-
counsel 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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24 Opinion of the Court 23-10061
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 ineffective-
assistance-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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23-10061 Opinion of the Court 29
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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30 Opinion of the Court 23-10061
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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23-10061 Opinion of the Court 31
AFFIRMED.
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