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No. 10035719
United States Court of Appeals for the Ninth Circuit
United States v. Heraclio Osorio-Arellanes
No. 10035719 · Decided August 9, 2024
No. 10035719·Ninth Circuit · 2024·
FlawFinder last updated this page Apr. 2, 2026
Case Details
Court
United States Court of Appeals for the Ninth Circuit
Decided
August 9, 2024
Citation
No. 10035719
Disposition
See opinion text.
Full Opinion
FOR PUBLICATION
UNITED STATES COURT OF APPEALS
FOR THE NINTH CIRCUIT
UNITED STATES OF AMERICA, No. 20-10003
Plaintiff-Appellee, D.C. No.
4:11-cr-00150-
v. DCB-LCK-4
HERACLIO OSORIO-ARELLANES,
AKA Laco, OPINION
Defendant-Appellant.
Appeal from the United States District Court
for the District of Arizona
David C. Bury, District Judge, Presiding
Argued and Submitted February 13, 2024
University of Arizona College of Law (Tucson)
Filed August 9, 2024
Before: Michael Daly Hawkins, Andrew D. Hurwitz, and
Roopali H. Desai, Circuit Judges.
Opinion by Judge Hawkins;
Dissent by Judge Hurwitz
2 USA V. OSORIO-ARELLANES
SUMMARY *
Criminal Law
The panel reversed the district court’s order
reconsidering its suppression of a confession by Heraclio
Osorio-Arellanes (“Osorio”), vacated his convictions and
sentences, and remanded for further proceedings.
Osorio participated in a chaotic firefight with U.S.
Customs and Border Patrol agents in Arizona. Osorio fled
back into Mexico, and one of the agents died from wounds
he sustained in the confrontation. Federal indictments and a
manhunt followed. Nearly seven years later, Osorio was
arrested by Mexican authorities and interrogated by U.S.
officials in a Mexico City prison. During this interrogation,
he confessed essential elements of the Government’s case on
the advice of a Mexican attorney, Juan Salvador Pimentel.
On direct appeal, Osorio claimed he is entitled to a new
trial because his confession was taken and admitted in
violation of his Fifth Amendment right against self-
incrimination and his Sixth Amendment right to effective
assistance of counsel.
The panel exercised its discretion to hear the Sixth
Amendment claim on direct appeal because (1) the record is
sufficiently developed in that there is no ambiguity as to
what Pimentel said to Osorio, and (2) the developed record
shows that Pimentel’s mid-interrogation advice—that
Osorio would not be affected if he confessed information
*
This summary constitutes no part of the opinion of the court. It has
been prepared by court staff for the convenience of the reader.
USA V. OSORIO-ARELLANES 3
about his intent toward drug smugglers because robbing drug
smugglers is not a crime—was obviously inadequate and
legally unjustifiable.
Addressing the substance of the claim under the
framework identified in Strickland v. Washington, 466 U.S.
668 (1984), the panel held (1) Pimentel’s counsel was
deficient; and (2) Pimentel’s advice was prejudicial because
there is a reasonable probability that, absent Pimentel’s
advice, Osorio would not have been convicted of any of the
charges.
Because Osario established his Sixth Amendment claim,
the panel did not need to reach his Fifth Amendment
claim. The panel rejected the Government’s argument that
the absence of a Fifth Amendment violation would bar
Osario’s Sixth Amendment claim.
Dissenting, Judge Hurwitz would affirm the conviction
and require Osorio to make his case for ineffective assistance
of counsel in the first instance in the district court through a
28 U.S.C. § 2255 motion.
COUNSEL
D. Benjamin Holley (argued), Special Attorney for the
United States; Daniel E. Zipp, and Fred Sheppard, Assistant
United States Attorneys; Andrew R. Haden, Acting United
States Attorney; Merrick B. Garland, Attorney General;
Department of Justice, Office of the United States Attorney,
San Diego, California; for Plaintiff-Appellee.
Tony F. Farmani (argued), Farmani PLC, Rancho Santa Fe,
California, for Defendant-Appellant.
4 USA V. OSORIO-ARELLANES
OPINION
HAWKINS, Circuit Judge:
By any measure, this is an extraordinary case. Late on
December 14, 2010, appellant-defendant Heraclio Osorio-
Arellanes (“Osorio”) participated in a chaotic firefight with
U.S. Customs and Border Patrol agents in a remote mountain
area south of Tucson, Arizona. When the shooting stopped,
Osorio fled into the night and, eventually, back into Mexico.
Tragically, one of the Border Patrol Agents, Brian Terry,
died from wounds he sustained in the confrontation.
Federal indictments and a manhunt followed. Nearly
seven years later, Osorio was arrested by Mexican
authorities and interrogated by U.S. officials in a Mexico
City prison. During this interrogation, he confessed essential
elements of the Government’s case on the advice of a
Mexican attorney. Before trial, Osorio’s American counsel
moved to exclude this confession, which the district court
initially suppressed on Sixth Amendment grounds but later
reversed following a Government motion for
reconsideration. As a result, the confession was introduced
at trial.
On direct appeal, Osorio claims he is entitled to a new
trial because his confession was taken and admitted in
violation of his Fifth Amendment right against self-
incrimination and his Sixth Amendment right to effective
assistance of counsel. For the reasons below, we conclude
that Osorio has established his Sixth Amendment claim.
Accordingly, we reverse the reconsideration order,
vacate Osorio’s convictions and sentences, and remand his
USA V. OSORIO-ARELLANES 5
case for proceedings consistent with the opinion that
follows. 1
BACKGROUND
I. The Crime.
Deep within the Atascosa Mountain Range, about fifty-
seven miles south of Tucson and eleven miles north of the
Mexican border, groundwater swells support a lush desert
oasis known as the Mesquite Seep. The surrounding terrain
is rough and remote. The area is covered with rigid peaks
and steep cliffs, so the Seep’s flora and fauna are only
accessible by single-lane footpaths and all-terrain vehicles.
These features make the Mesquite Seep a choice destination
for hikers and nature enthusiasts. They also made it an
excellent drug trafficking corridor.
For years, couriers carried marijuana in backpacks across
the Seep. At some point, perhaps sensing opportunity, small
gangs known as “rip crews” began robbing drug couriers at
gunpoint. The Tucson Sector of the United States Border
Patrol Tactical Unit (“BORTAC”) eventually caught wind
of this activity and developed “Operation Huckleberry” to
apprehend armed individuals prowling the area. The
operation mostly consisted of BORTAC agents patrolling
the Seep while lookouts monitored radio traffic and an
intricate system of motion sensors. When sensors went off,
lookouts confirmed the trigger source and deployed armed
ground agents to confront suspected rip crews.
This is what happened around 11:00 pm on December
14, 2010. BORTAC Agents William Castano (the team
1
We vacate Osorio’s 18 U.S.C. § 924(c) conviction and sentence
pursuant to United States v. Taylor, 145 S. Ct. 2015 (2022).
6 USA V. OSORIO-ARELLANES
leader), Gabriel Fragoza, Timothy Keller, and Brian Terry
were nearing the end of a forty-eight-hour shift in the Seep
when one of their lookouts, Agent Charles Veatch, alerted
them of individuals approaching their location. Visibility
was bad that night, but Agent Castano spotted an armed
group through a thermal imaging device and ordered his
team to form a line on higher ground.
When the armed group was about fifteen yards away,
Castano yelled down to them, “Policia! Policia! Policia!”
Some members of the armed group ran, but others drew their
weapons. Agent Fragoza yelled out several times in Spanish
for the men to “get down” before firing a non-lethal round
from his shotgun in the group’s direction. A chaotic firefight
erupted.
The exchange only lasted a few seconds. But, in the
affray, Osorio’s brother Manuel was wounded, and Agent
Terry sustained a gunshot wound to his torso. Despite his
fellow agents’ attempts to provide life-saving care, Agent
Terry lost consciousness at the scene and was pronounced
dead on arrival at a nearby hospital. Manuel was treated by
first responders and taken into federal custody. The
remaining Border Patrol agents were unharmed, and the rest
of the armed group escaped.
II. The Aftermath: Investigation, Indictment, and
Interrogation.
The next day, an investigative team led by FBI Agent
Michelle Terwilliger collected evidence from the scene,
including spent shell casings and five backpacks loaded with
food, water, ammunition, and portable battery charging
devices for cell phones. Forensic pathologists later surmised
that Agent Terry was killed by an AK-47 bullet fired from a
downhill position, but, as a practical matter, the shooter
USA V. OSORIO-ARELLANES 7
could not be identified. Nevertheless, the FBI lab at
Quantico, Virginia placed Osorio at the scene based on DNA
evidence recovered from a water bottle he left behind.
On August 24, 2011, a federal grand jury returned an
indictment, charging Osorio and four other men on nine
counts for their participation in Agent Terry’s death. The
Fifth Superseding Indictment (“the Indictment”) is the
operative indictment. It includes the following counts: first-
and second-degree murder under 18 U.S.C. §§ 1111 and
1114 (Counts One and Two); conspiracy to interfere with
commerce by robbery and attempted inference with
commerce by robbery under the Hobbs Act, 18 U.S.C.
§ 1951 (Counts Three and Four, hereinafter “the robbery
charges”); four counts of assault on a federal officer under
18 U.S.C. § 111 (Counts Five through Eight); and the use
and carrying a firearm during a crime of violence under 18
U.S.C. § 924(c) (Count Nine). Because it was impossible to
determine which rip crew member fired the fatal shot, the
Indictment advanced a felony-murder theory predicated on
the robbery charges. 2 Indeed, it is undisputed that the
Government needed to establish the robbery charges in order
to secure convictions on every remaining count.
After the Indictment issued, extradition proceedings
were initiated, provisional arrest warrants were executed,
and, over the next several years, authorities apprehended,
extradited, and convicted other members of the armed group.
2
Essentially, the theory was that Osorio’s group killed Agent Terry
during an attempted Hobbs Act robbery because they were allegedly in
the Seep to rob drug smugglers, and “[m]arijuana is brought from
Mexico into the United States . . . by the drug smugglers. When that
marijuana enters the United States from Mexico, it has traveled in
foreign commerce, which is part of interstate commerce.”
8 USA V. OSORIO-ARELLANES
See United States v. Osorio-Arellanes et al., 11-cr-0150-
DCB-BGM; United States v. Soto-Barraza, 947 F.3d 1111,
1114 (9th Cir. 2020) (affirming convictions of two co-
defendants). Osorio was arrested by Mexican authorities on
April 12, 2017. While his extradition proceedings were
underway, the Mexican Attorney General’s office arranged
an interrogation with U.S. officials in Reclusorio Sur, a
Mexico City prison.
The U.S. officials arrived at the prison on July 27, 2017.
FBI Special Agents Michael Dreher and Tenoch Aguilar
conducted the questioning in Spanish in the presence of
then-Assistant United States Attorney (“AUSA”) Todd
Robinson and Agent Terwilliger. Authorities from the
Mexican Attorney General’s office were also present. When
the U.S. contingent arrived, Mexican officials told them that
Osorio had requested the presence of his attorney, although
there is some disagreement about who that was. The group
waited for almost three hours to honor Osorio’s request, but
his attorney never showed up. One of the Mexican officials
eventually suggested that a prison attorney might represent
Osorio during the interrogation, but he declined this
suggestion. Agent Dreher encouraged Osorio to at least
speak with the prison attorney before deciding, but Osorio
declined again.
Shortly thereafter, a Mexican attorney named Juan
Salvador Pimentel Ramirez (“Pimentel”) entered the scene.
It is unclear where Pimentel came from or what he was doing
at the prison that day. 3 Still, according to the interrogation
3
As the district court noted at the initial suppression hearing: “Now, the
facts that I don’t have are, and I could have had but I don’t have, Pimentel
didn’t drop out of a bag at this prison. Somebody had to call him, contact
USA V. OSORIO-ARELLANES 9
transcript, he spoke with the authorities and explained he had
not “been in [Osorio’s] case file,” and that another attorney,
Jonathan Toledo, was named in the extradition file. A
Mexican official assured him this did not matter because
they were only there “for public assistance, just to fulfill the
requirement,” not for “the extradition proceeding.”
Apparently satisfied, Pimentel spoke privately with Osorio
for about ten minutes, Osorio consented to his
representation, and the interrogation began.
Agent Dreher confirmed that Osorio had conferred with
his attorney before reading his Miranda warnings and asking
whether he had any questions. Osorio said nothing, but
Pimentel chimed in to express confusion about the
interrogation’s underlying nature: “I don’t know, if you’ll
allow me. Is this just the part pertaining to . . . the United
States Department of Justice, or is it just the, what’s it
called? The part having to do with the police
investigation . . . of what this investigation is about?” Agent
Dreher explained that he and Agent Aguilar were “just here
to find out . . . what happened,” and Agent Aguilar affirmed
that they were “just learning.” An unidentified speaker
nevertheless expressed that “they prosecute.”
The agents then began questioning Osorio about the
night of Agent Terry’s death. Osorio confirmed he was
present during the shooting, identified other members of the
group, and explained their encounter with Border Patrol.
Agent Dreher soon turned to the group’s motivation.
When asked why they were walking through the Seep
that night, Osorio claimed that the group only intended to
him, hire him, request him, instruct him, or ask him to come to this
statement.”
10 USA V. OSORIO-ARELLANES
pick up food to “drop off in certain spots.” On further
questioning, Osorio’s answer was the same: “They’d send us
to drop off food on the roads.” The agents apparently did
not believe this story and continued to push the point: “But,
what was the group’s purpose?” Osorio responded, “Well,
they paid us to go drop food off, like I said.” When the
agents asked why the group carried weapons, Osorio noted
their need for protection: “[T]here are a lot of bad people in
the mountains.”
As the interrogation went on, the agents tried other
interrogation techniques to uncover Osorio’s intentions
toward drug smugglers. They claimed his co-defendants and
family members had told them a different story. They
pressed Osorio for specifics about dropping off the food,
claimed they already knew he intended to rob drug
smugglers as “a fact,” and implored him to tell the truth.
They also empathized with his plight, noting the lack of
work in his home state of Sinaloa and claiming they would
not blame him for doing something illegal. At one point,
Agent Dreher stated, with full knowledge of the Indictment
charging otherwise, “[w]e’re not charging you . . . with what
you [sic] were doing against the drug runners, that has
nothing to do with it.” But Osorio did not bite.
That changed, however, when Pimentel offered some
legal advice:
Heraclio, on your behalf and as your lawyer,
I can tell you in front of all of them, . . . they
can’t establish that you committed that crime,
I mean, how is it possible for you to rob
somebody . . . who was carrying out an
illegal activity . . . I mean . . . there’s no crime
USA V. OSORIO-ARELLANES 11
for another crime, right? So since they’re
alleging that you’re affecting . . . the drug
runner’s trade . . . it will not affect you if you
tell them about it.
On these assurances, Osorio began providing authorities
with incriminating information about his intent to rob drug
smugglers in the Seep. For example, Agent Dreher’s next
question was, “When you robbed the drug runners, how
much did they pay you?” to which Osorio responded, “Well,
it depends, maybe ten thousand.” He went on to offer other
incriminating admissions, such as his knowledge of the
Mesquite Seep’s terrain and the types of drugs that
smugglers carried. He also admitted five previous attempts
to rob drug smugglers, including specific logistical details
about those attempts, and disclosed that he had previously
smuggled drugs through the area.
Finally, the agents asked whether anyone had
specifically instructed the group to rob drug smugglers in the
Seep on the night of the shootout. Osorio answered in the
affirmative, and an agent followed up, “But . . . did you also
know” to go to the Seep “because you’d been through there
before?” “Yes,” he replied, “well, more or less,” thus
confirming his past experiences with robbing drug
smugglers and his intent to rob drug smugglers on the night
of Agent Terry’s death.
JURISDICTION AND STANDARD OF REVIEW
We have jurisdiction under 28 U.S.C. § 1291. “We
review de novo the district court’s denial of a motion to
suppress.” United States v. Morgan, 738 F.3d 1002, 1005
(9th Cir. 2013). We also review constitutional questions de
novo. See United States v. Benlian, 63 F.3d 824, 826 (9th
12 USA V. OSORIO-ARELLANES
Cir. 1995) (Sixth Amendment); United States v. Hulen, 879
F.3d 1015, 1018 (9th Cir. 2018) (Fifth Amendment).
We review the district court’s factual findings for clear
error. United States v. Bassignani, 575 F.3d 879, 883 (9th
Cir. 2009). These factual findings include “scene and
action-setting questions,” and “the circumstances” of an
interrogation. Id. (quoting Thompson v. Keohane, 516 U.S.
99, 112 (1995)). But “[t]he finding of a knowing and
voluntary waiver is a mixed question of law and fact which
we review de novo.” Campbell v. Wood, 18 F.3d 662, 672
(9th Cir. 1994) (en banc).
ISSUES
In this direct appeal, Osorio claims he is entitled to a new
trial because his confession was taken and admitted in
violation of his Fifth Amendment right against self-
incrimination and his Sixth Amendment right to effective
assistance of counsel. The Government argues that no
constitutional violations occurred, and even if they did:
(1) the record is insufficiently developed to consider
Osorio’s Sixth Amendment claim on direct appeal; (2) his
Sixth Amendment claim is barred by his Fifth Amendment
waiver; and (3) no court has ever considered an ineffective
assistance of counsel claim in this context.
For the reasons below, we conclude that Osorio has
established his Sixth Amendment claim. Our analysis
proceeds as follows: First, we exercise our discretion to
consider Osorio’s Sixth Amendment claim on direct appeal.
Second, we resolve the substance of that claim in his favor
under the framework identified in Strickland v. Washington,
466 U.S. 668 (1984). Finally, we reject the Government’s
contention that Osorio’s Sixth Amendment claim rose and
fell with his Fifth Amendment claim.
USA V. OSORIO-ARELLANES 13
I. Direct Review.
As a threshold matter, we must decide whether to
consider Osorio’s Sixth Amendment claim on direct appeal.
“[T]he decision to defer resolution of an ineffective
assistance of counsel claim is a discretionary one.” United
States v. Miskinis, 966 F.2d 1263, 1269 (9th Cir. 1992).
“However, as a general rule, we do not review challenges to
the effectiveness of defense counsel on direct appeal.”
United States v. Jeronimo, 398 F.3d 1149, 1155 (9th Cir.
2005), overruled on other grounds by United States v.
Jacobo Castillo, 496 F.3d 947, 957 (9th Cir. 2007) (en
banc). The rationale for the general rule is that ineffective
assistance of counsel claims “usually . . . cannot be advanced
without the development of facts outside the original
record.” Jeronimo, 398 F.3d at 1156 (quoting United States
v. Birges, 723 F.2d 666, 670 (9th Cir. 1984)).
The general approach reflects this Court’s concern that
appellate courts might “become engaged in the perilous
process of second-guessing.” Birges, 723 F.2d at 670
(quoting People v. Pope, 590 P.2d 859, 867 (Cal. 1979)).
Without a fully developed record:
Reversals would be ordered unnecessarily in
cases where there were, in fact, good reasons
for the aspect of counsel’s representation
under attack. Indeed, such reasons might
lead a new defense counsel on retrial to do
exactly what the original counsel did, making
manifest the waste of judicial resources
caused by reversal on an incomplete record.
Id.
14 USA V. OSORIO-ARELLANES
Nevertheless, there are two exceptions to our general
rule. We may consider Sixth Amendment claims on direct
appeal when: (1) the record “is sufficiently developed,” or
(2) an attorney’s performance is “so inadequate that it
obviously denies a defendant his Sixth Amendment right to
counsel.” Jeronimo, 398 F.3d at 1156. Both exceptions
apply here.
A. There is no ambiguity about “what” Pimentel
said.
To start, the ineffectiveness alleged on appeal—
Pimentel’s erroneous legal advice—stems from a single
incident that is fully reflected in the interrogation transcript.
See United States v. Alferahin, 433 F.3d 1148, 1161 n.6 (9th
Cir. 2006) (“Defense counsel’s alleged ineffectiveness in
this case stems from a specific and discrete conversation,
recorded clearly in the record.”). In some cases, additional
information may be needed to understand “what” advice an
attorney gave. See United States v. Pope, 841 F.2d 954, 958
(9th Cir. 1988) (explaining that in many cases a defendant
must “develop a record as to what counsel did” and “why it
was done”). However, when a Sixth Amendment violation
is based on an isolated instance of an attorney’s recorded
conduct, this Court may properly exercise its discretion to
consider the claim. 4 Thus, Osorio’s Sixth Amendment claim
is ripe for direct review.
Nevertheless, our dissenting colleague notes that “[o]n
the few occasions when we have found a record sufficiently
4
See United States v. Swanson, 943 F.2d 1070, 1072 (9th Cir. 1991) (“In
pursuing his claim of ineffectiveness of counsel, Swanson relies solely
on the reported statements made by Mr. Ochoa during final argument.
Accordingly, the record is sufficient for a review of the merits of
Swanson’s constitutional claim on this direct appeal.”).
USA V. OSORIO-ARELLANES 15
developed to depart from this customary practice, that record
was usually made in a judicial proceeding.” True as that may
be, the Sixth Amendment’s protections indisputably cover
deficient conduct that occurs outside of formally
adjudicative settings, and the Government concedes that the
Sixth Amendment applied during the interrogation. See
Missouri v. Frye, 566 U.S. 134, 140 (2012) (“It is well
settled that the right to the effective assistance of counsel
applies to certain steps before trial,” including
“postindictment interrogations.”); United States v. Leonti,
326 F.3d 1111, 1114, 1117 (9th Cir. 2003) (discussing
potential ineffective assistance of counsel claim arising from
an attorney’s conduct in the “pre sentencing cooperation
period”). The Government does not argue that its self-
produced transcript is inaccurate, so it is unclear how the
source of this evidence precludes our direct review.
Moreover, the parties already received a full and fair
opportunity to develop relevant facts during a judicial
proceeding: Before trial, the district court held an
evidentiary hearing on Osorio’s Fifth and Sixth Amendment
claims. There, the court considered evidence like the
interrogation transcript and the advice-of-rights form that
Osorio was provided at the beginning of his interrogation.
During the hearing, Agent Dreher also testified about the
Government’s efforts to coordinate the interrogation with
Mexican officials, the nature of Osorio’s detention and his
extradition status, and the circumstances of Pimentel’s
involvement in the interrogation.
Nothing further would be developed in habeas
proceedings. To start, there is no mechanism to compel
Pimentel’s testimony because “federal courts lack power to
secure the appearance of a foreign national located outside
the United States,” and Pimentel is a Mexican national
16 USA V. OSORIO-ARELLANES
domiciled in Mexico. States v. Beyle, 782 F.3d 159, 170 (4th
Cir. 2015). 5 Furthermore, Osorio was available to testify
during the evidentiary hearing, and the defense did not call
him as a witness. The Americans who attended the
interrogation––Agent Dreher, Agent Terwilliger, Agent
Aguilar, and Attorney Robinson––were also available for
testimony, but only Agent Dreher was called. He testified
that he spoke directly with Pimentel outside of the recorded
interrogation but that he does not recall the content of their
conversation. And, although “[t]he transcript includes over
one hundred ‘unintelligible’ markings,” the parties did not
raise this argument on appeal, and Agent Dreher was asked
about the markings during the evidentiary hearing. 6 No one
genuinely disputes the content of Pimentel’s advice. In this
respect, the record is fully developed.
Nor is further record development needed to determine
whether Osorio somehow assumed the risk of Pimentel’s
limited knowledge of American law. No part of the Sixth
Amendment analysis turns on what a criminal defendant
knows about their attorney’s qualifications, and criminal
defendants do not waive their right to effective assistance of
counsel by choosing their lawyers. See United States v.
Mouzin, 785 F.2d 682, 698 (9th Cir. 1986) (“[A] lawyer’s
services [are] ineffective on a case, not a per se, basis.”).
5
See also United States v. Theresius Filippi, 918 F.2d 244, 247 (1st Cir.
1990) (“The government has no power to compel the presence of a
foreign national residing outside the United States.”); United States v.
Zabaneh, 837 F.2d 1249, 1259–60 (5th Cir. 1988) (same); see also 28
U.S.C. § 1783(a) (providing for subpoenas of “a national or resident of
the United States who is in a foreign country,” but not referencing
foreign nationals abroad); Fed. R. Crim. P. 17(e)(2).
6
Agent Dreher answered questions about instances where unintelligible
markings might have obscured relevant portions of the transcript.
USA V. OSORIO-ARELLANES 17
Instead, “the appropriate inquiry focuses on the adversarial
process, not on the accused’s relationship with his lawyer as
such. If counsel is a reasonably effective advocate, he meets
constitutional standards irrespective of his client’s
evaluation of his performance.” United States v. Cronic, 466
U.S. 648, 657 n.21 (1984). Osorio’s beliefs about Pimentel’s
efficacy simply have no bearing on our Sixth Amendment
analysis.
Importantly, the right to effective assistance of counsel
exists because it has long been understood that “[a] layman
will ordinarily be unable to recognize counsel’s errors and to
evaluate counsel’s professional performance.” Kimmelman
v. Morrison, 477 U.S. 365, 378 (1986). Yet, the Government
asks us to suppose that Osorio waived this right because he
was sufficiently proficient in comparative criminal law to
appreciate the risks posed by accepting foreign
representation during the critical stages of American
proceedings. Under Strickland and its progeny, we cannot
make that assumption. See Maine v. Moulton, 474 U.S. 159,
169 (1985) (noting that the right to counsel embodies “a
realistic recognition of the obvious truth that the average
defendant does not have the professional legal skill to protect
himself” (quoting Johnson v. Zerbst, 304 U.S. 458, 462–63
(1938)).
And, as a more general matter, we will not, especially
where the forced choice between foreign and domestic
counsel was made “possible only under color of state
authority, and wholly within the power of the State to
prevent.” Vasquez v. Hillery, 474 U.S. 254, 262 (1986).
There is no dispute that the Government initiated extradition
proceedings against Osorio and facilitated his interrogation
with Mexican officials. There is also no dispute about why
the interrogation took place in Mexico: During the
18 USA V. OSORIO-ARELLANES
evidentiary hearing, the district court asked why the
Government did not simply wait to interrogate Osorio in the
United States, where he would soon be physically present,
immediately arraigned, and assigned an American attorney.
The Government responded that the investigative team
wanted to continue searching for another fugitive in Mexico.
No further justification was suggested during the hearing nor
when the question was raised again during oral argument.
Although the Government’s investigative interest is
entirely legitimate, this expediency concern does not trump
fundamental constitutional rights when a criminal defendant
is already in foreign custody and subject to ongoing
extradition proceedings. Sell v. United States, 539 U.S. 166,
180 (2003) (noting that, in addition to its “substantial interest
in timely prosecution,” the Government “has a concomitant,
constitutionally essential interest in assuring that the
defendant’s trial is a fair one.”); see also Moulton, 474 5 U.S.
at 170 (“[T]o deprive a person of counsel during the period
prior to trial may be more damaging than denial of counsel
during the trial itself.”). There is no suggestion that Osorio
was at risk of escape. Thus, he did not assume the risk of the
Government’s decision to interrogate him in a location
where the type of constitutional violation at issue was far
more likely to occur. See Moulton, 474 U.S. at 174 (“[B]y
intentionally creating a situation likely to induce [defendant]
to make incriminating statements without the assistance of
counsel, the Government violated [his] Sixth Amendment
right to counsel.” (quoting United States v. Henry, 447 U.S.
264, 274 (1980))).
The investigative team could have continued searching
for the fugitive and waited to interrogate Osorio in the
United States where his rights likely would have been much
better protected. See Addington v. Texas, 441 U.S. 418, 427
USA V. OSORIO-ARELLANES 19
(1979) (“The individual should not be asked to share equally
with society the risk of error when the possible injury to the
individual is significantly greater than any possible harm to
the state.”). Under these circumstances, “[t]he Sixth
Amendment mandates that the State bear the risk of
constitutionally deficient assistance of counsel.”
Kimmelman, 477 U.S. at 379. Not Osorio.
Although the material facts on appeal are unusual, they
are not unclear: Our legal analysis does not require any
“facts we don’t have” or could reasonably hope to obtain.
The record is developed in every material respect.
B. The developed record also shows that Pimentel’s
mid-interrogation advice was obviously
inadequate and legally unjustifiable.
Moreover, even if there are facts we might like to have,
we do not need them because the interrogation transcript
shows that Pimentel’s advice was so inadequate that it
obviously denied Osorio’s Sixth Amendment right to
effective assistance of counsel. Under Strickland, counsel’s
strategic judgments are owed heavy deference. 466 U.S. at
689 (“[T]he defendant must overcome the presumption that,
under the circumstances, the challenged action ‘might be
considered sound trial strategy.’” (quoting Michel v.
Louisiana, 350 U.S. 91, 101 (1955))). Thus, ineffective
assistance of counsel claims are ordinarily more
appropriately evaluated during post-conviction proceedings,
where evidentiary hearings might shed light on counsel’s
strategic reasoning. See, e.g., United States v. McGowan,
668 F.3d 601, 606 (9th Cir. 2012) (declining review when
reviewing court could not “tell from [the] record whether the
[failure] . . . was a calculated stratagem or a mere oversight”
20 USA V. OSORIO-ARELLANES
(internal citation omitted)). 7 However, when counsel
unquestionably acts (or fails to act) based on a mistaken legal
or factual understanding, their conduct lacks strategic reason
as a matter of law. Wiggins v. Smith, 539 U.S. 510, 526
(2003) (noting that when a “failure to investigate thoroughly
resulted from inattention,” it is “not strategic judgment.”).
Pimentel’s advice was blatantly incorrect. He stated that
Osorio would not be affected if he confessed information
about his intent toward drug smugglers because robbing drug
smugglers is not a crime. Of course, robbing drug smugglers
is a crime––and not only that: it was the precise crime
Osorio was charged with committing under the Hobbs Act
and the predicate offense to a first-degree murder charge that
carried a mandatory life sentence. 8 There is simply no
justifiable reason for this advice. Jones v. Wood, 114 F.3d
1002, 1010 (9th Cir. 1997) (“Even if [Pimentel’s] decision
could be considered one of strategy, that does not render it
7
See also United States v. Lillard, 354 F.3d 850, 856 (9th Cir. 2003)
(failure to call alibi witnesses); United States v. Reyes-Platero, 224 F.3d
1112, 1116 (9th Cir. 2000) (failure to request downward departure),
overruled on other grounds by Jacobo Castillo, 496 F.3d at 957.
8
The record shows that Pimentel had a valid professional license in
Mexico, which was issued by the Department of Public Education,
General Directorate of Professions. Nevertheless, whether Pimentel’s
counsel was reasonable by Mexican standards is entirely irrelevant to
this analysis. Strickland, 466 U.S. at 697 (“The object of an
ineffectiveness claim is not to grade counsel’s performance.”).
Whatever the prevailing law in Mexico, we must measure Pimentel’s
conduct in relation to Osorio’s Sixth Amendment right to meet the
prosecution’s case in an American proceeding. Id. at 690 (“[T]he court
should keep in mind that counsel’s function, as elaborated in prevailing
professional norms, is to make the adversarial testing process work in
the particular case.”). Any contrary suggestion ignores Strickland’s
objective and its only source of legitimacy.
USA V. OSORIO-ARELLANES 21
immune from attack—it must be a reasonable strategy.”
(emphasis in the original)). It is objectively unreasonable, in
any circumstances, to encourage a client’s confession to live
charges––without securing any deal from the prosecution––
based on a blatant misunderstanding of case-determinative
law.
No additional evidence could change that fact or render
Pimentel’s advice retroactively reasonable. Noguera v.
Davis, 5 F.4th 1020, 1046 (9th Cir. 2021) (“[C]ourts may not
indulge ‘post hoc rationalization’ for counsel’s
decisionmaking that contradicts the available evidence of
counsel’s actions.” (quoting Harrington v. Richter, 562 U.S.
86, 109 (2011))). The transcript clearly demonstrates that
Pimentel was simply wrong, and thus, his counsel was so
inadequate that it obviously denied Osorio’s Sixth
Amendment right to effective assistance of counsel.
Accordingly, we exercise our discretion to hear his Sixth
Amendment claim on direct appeal.
II. The Sixth Amendment: Strickland v. Washington.
We now turn to Strickland. The Sixth Amendment’s
Counsel Clause guarantees “[i]n all criminal prosecutions,
the accused shall enjoy the right . . . to have the Assistance
of Counsel for his defence.” U.S. Const. amend. VI. The
Sixth Amendment right to counsel is “offense specific” and
thus attaches at “the initiation of adversary judicial criminal
proceedings,” e.g., at indictment. Texas v. Cobb, 532 U.S.
162, 168 (2001) (quoting McNeil v. Wisconsin, 501 U.S.
171, 175 (1991)). And the right to effective assistance of
counsel “applies to pretrial critical stages that are part of the
whole course of a criminal proceeding, a proceeding in
which defendants cannot be presumed to make critical
decisions without counsel’s advice.” Lafler v. Cooper, 566
22 USA V. OSORIO-ARELLANES
U.S. 156, 165 (2012). 9 “Interrogation by the State is such a
stage.” Montejo v. Louisiana, 556 U.S. 778, 786 (2009);
Massiah v. United States, 337 U.S. 201, 204 (1964) (“[A]
Constitution which guarantees a defendant the aid of counsel
at such a trial could surely vouchsafe no less to an indicted
defendant under interrogation by the police in a completely
extrajudicial proceeding.”).
There are several dimensions to the Sixth Amendment
right to counsel. There is the paradigmatic application “that,
with certain exceptions, a person accused of a federal or state
crime has the right to have counsel appointed if retained
counsel cannot be obtained.” Strickland, 466 U.S. at 685.
Another “element of this right is the right of a defendant who
does not require appointed counsel to choose who will
represent him.” United States v. Gonzalez-Lopez, 548 U.S.
140, 144 (2006). “That a person who happens to be a lawyer
is present . . . alongside the accused, however, is not enough
to satisfy the constitutional command.” Strickland, 466 U.S.
at 685. “[A]ccess to counsel’s skill and knowledge is
necessary to accord defendants the ample opportunity to
meet the case of the prosecution to which they are entitled.”
Kimmelman, 477 U.S. at 384 (internal citations and
punctuation omitted). Thus, the Supreme Court has also
recognized that “the right to counsel is the right to the
effective assistance of counsel.” Strickland, 466 U.S. at 686
(emphasis added) (internal citation omitted).
To succeed on a claim for ineffective assistance of
counsel, a defendant must show that their attorney’s
9
Because the Sixth Amendment right to counsel is “offense” (not
“location”) specific, we need not consider its extraterritorial application,
especially when the prejudice alleged––and thus the ultimate
constitutional violation––occurred in the United States.
USA V. OSORIO-ARELLANES 23
performance was deficient and prejudicial. Strickland, 466
U.S. at 687.
A. Pimentel’s counsel was deficient.
To prove deficiency, “the defendant must show that
counsel’s representation fell below an objective standard of
reasonableness.” Id. at 688. That is, “a criminal defendant’s
counsel may be deemed ineffective only if counsel’s
performance falls outside the wide range of reasonable
professional assistance.” United States v. Juliano, 12 F.4th
937, 940 (9th Cir. 2021) (quoting Torres-Chavez v. Holder,
567 F.3d 1096, 1100–01 (9th Cir. 2009)). “‘[S]crutiny of
counsel’s performance must be highly deferential, and the
defendant must overcome the presumption that, under the
circumstances, the challenged action might be considered
sound trial strategy.’” Id. “In particular, we must evaluate
the conduct from counsel’s perspective at the time, taking
care not to view a lawyer’s decisions in the distorting effects
of hindsight.” Id.
The Government finds itself in a strange position here:
while arguing that Pimentel acted as Osorio’s lawyer for
Miranda purposes, it also argues that Pimentel was not
acting as “counsel” for Sixth Amendment purposes because
he is not licensed to practice law in the United States. As
both a practical and legal matter, however, Pimentel acted as
Osorio’s counsel during the interrogation. The transcript
makes clear that the relevant parties––the interrogating
agents, Osorio, and Pimentel––understood that Pimentel was
24 USA V. OSORIO-ARELLANES
Osorio’s attorney during the interrogation. 10 Pimentel was
physically present during questioning, asserted himself as
Osorio’s counsel at several points, and attempted to advocate
for him throughout the interrogation.
The Government also submitted post-interrogation
documentation, apparently signed by all relevant parties,
affirmatively stating that Pimentel was Osorio’s “private
attorney.” Nevertheless, the Government now claims that no
court has found that “a person, selected by the defendant and
who is licensed to practice law only in a foreign country, can
be liable for ineffective assistance of counsel.” Putting
aside these conflicting positions, and that Strickland does not
subject attorneys to personal liability for their deficient
performance, the issue is not so uncharted as the
Government suggests.
It is settled law in this Circuit that an attorney’s law
license does not tip Strickland’s deficiency analysis. We
have recognized that, in certain circumstances, unlicensed
attorneys can serve as “counsel” for Sixth Amendment
purposes. United States v. Hoffman, 733 F.2d 596, 599 (9th
Cir. 1984) (rejecting defendant’s argument that upon
disbarment, his attorney was no longer “counsel” within the
Dreher: “I just handed this to you and to the gentleman, your attorney,
10
who is here.”
...
Dreher: “[Y]ou have your attorney with you here today.”
Osorio: “Yes.”
...
Pimentel: “[L]ook, Heraclio, on your behalf and as your lawyer . . . .”
USA V. OSORIO-ARELLANES 25
meaning of the Sixth Amendment). 11 Although “the Sixth
Amendment guarantee of counsel means assistance by an
attorney who has been found qualified to represent a client
as evidenced by admission to the bar,” unlicensed attorneys
are not “automatically disqualified” from a case, and their
services cannot be deemed per se ineffective “without regard
to their intrinsic quality.” Mouzin, 785 F.2d at 696.
Foreign attorneys representing indicted defendants in
U.S.-initiated proceedings should not be measured by a
separate standard. In many circumstances, foreign attorneys
will certainly provide adequate counsel during overseas
interrogations––a foreign attorney might have advised
Osorio to remain silent based on their existing knowledge of
American law, cursory research efforts, or even chance
overlap between our respective national laws. 12 Whatever
the source of their advice, we are reluctant to hold that
foreign attorneys can never be “counsel” for Sixth
Amendment purposes. Indeed, such a holding would impede
the Government’s ability to conduct interrogations abroad
and would sometimes require suppressing extraterritorial
admissions at trial, even when, by American standards, the
defendant’s statements were provided on a foreign
attorney’s objectively superlative counsel. If a foreign
11
See also Cronic, 466 U.S. at 665 (“The character of a particular
lawyer’s experience may shed light in an evaluation of his actual
performance, but it does not justify a presumption of ineffectiveness in
the absence of such an evaluation.”).
12
In fact, this has happened before. In United States v. Straker, 596 F.
Supp. 2d 80, 85 (D.D.C. 2009), Straker followed his Trinidadian
attorney’s advice “not to sign any documents or speak to anyone” when
the FBI was investigating his involvement in the kidnapping of a U.S.
citizen.
26 USA V. OSORIO-ARELLANES
attorney’s advice enables a criminal defendant to meet the
prosecution’s case, their counsel is competent.
However, Pimentel’s advice did not. Even under
Strickland’s highly deferential lens, his counsel was plainly
deficient. It is widely understood that “during
postindictment questioning, a lawyer’s role is rather
unidimensional: largely limited to advising his client as to
what questions to answer and which ones to decline to
answer.” Patterson v. Illinois, 487 U.S. 285, 294 n.6 (1988).
Pimentel unquestionably failed to fulfill this role:
Objectively reasonable counsel would never encourage a
defendant’s confession to live charges without first securing
any agreement from the prosecution. 13
If Pimentel’s advice was a “strategic decision,” it was not
a permissible one. The interrogation transcript demonstrates
his fundamental ignorance on dispositive points of law, such
as the intent to commit robbery under the Hobbs Act and
felony murder. Hinton v. Alabama, 571 U.S. 263, 274
(2014) (per curiam) (“An attorney’s ignorance of a point of
law that is fundamental to his case combined with his failure
to perform basic research on that point is a quintessential
example of unreasonable performance under Strickland.”).
13
Consider this exchange between the Government and the district court
during the pre-trial hearing on the motions to suppress:
Government: “I would agree with the court that most
criminal defense attorneys would instruct their client
not to answer questions when the FBI seeks to
interview their client.”
District Court: “Post indictment, without the offer of
any deal, is there any lawyer that would let Mr. Osorio
give this statement that he gave? [] I think I know the
answer to that question already.”
USA V. OSORIO-ARELLANES 27
For example, while discussing the act of robbing drug
smugglers, Pimentel said, “That can’t be a crime. I don’t
know if in the United States, like, how can you rob drugs
from somebody illegal, and here it can be . . . uh, I mean, I
don’t understand that.” When discussing the charges, he
asked, “what are the elements of first degree murder?”
Further, long after he encouraged Osorio to admit essential
elements of the Government’s case, Pimentel thought to ask,
“Is it possible that, just as you have a protected witness who,
[] was able to negotiate with the justice system [] in the
United States, that some of [Osorio’s] testimony might work
[] to benefit him? Here in Mexico you can negotiate.”
Still, “a particular decision not to investigate must be
directly assessed for reasonableness in all the circumstances,
applying a heavy measure of deference to counsel’s
judgments.” Strickland, 466 U.S. at 691. Sometimes, a
decision not to investigate is not deficient counsel when an
attorney reasonably believes that additional investigation
would be futile or when they decide to pursue one reasonable
strategic line of investigation over another. See Harrington,
562 U.S. at 110 (“Richter’s attorney was mistaken in
thinking the prosecution would not present forensic
testimony. But the prosecution itself did not expect to make
that presentation and had made no preparations for doing so
on the eve of trial.”); see also Rompilla v. Beard, 545 U.S.
374, 383 (2005) (“[R]easonably diligent counsel may draw
a line when they have good reason to think further
investigation would be a waste.”). But “strategic choices
made after less than complete investigation are reasonable
precisely to the extent that reasonable professional
judgments support the limitations on investigation.” Burger
v. Kemp, 483 U.S. 776, 794 (1987) (quoting Strickland, 466
U.S. at 690–91).
28 USA V. OSORIO-ARELLANES
No reasonable professional judgment supports the
limited nature of Pimentel’s investigation. The interrogation
transcript shows that Pimentel’s advice stemmed from his
misunderstanding of the underlying law and facts of
Osorio’s case. See Kimmelman, 477 U.S. at 384 (noting that
the adversarial “testing process generally will not function
properly unless defense counsel has done some investigation
into the prosecution’s case and into various defense
strategies”). Objectively reasonable defense counsel would
have spent more than ten minutes conferring with his client
and would have reviewed the charges against him and his
extradition file, especially when dealing with foreign
authorities. Rompilla, 545 U.S. at 385 (finding deficient
counsel where “even after obtaining the transcript of the
victim’s testimony on the eve of the sentencing hearing,
counsel apparently examined none of the other material in
the file”).
Even if Pimentel was confused about the interrogation’s
nature, that confusion was not a reasonable professional
judgment that can support his failure to investigate.
Kimmelman, 477 U.S. at 385 (finding that an attorney’s
failure to conduct pretrial discovery based on a mistaken
legal understanding was not “strategy”). At the
interrogation’s outset, the Government was clear that
anything Osorio said could be used against him in a court of
law. Pimentel was also told that the investigating agents and
“the prosecutor handling the case” in the United States were
present. Upon hearing the Miranda warnings and being
alerted of the prosecutor’s presence, objectively reasonable
counsel would not have allowed the interrogation to continue
without conducting at least some colorable investigation into
the circumstances of Osorio’s alleged crimes, the posture of
USA V. OSORIO-ARELLANES 29
his case, and the legal theories supporting the charges against
him. Pimentel did none of that.
Thus, his counsel was deficient.
B. Pimentel’s advice was prejudicial.
Because Osorio has proved Pimentel’s counsel was
deficient, we must consider whether it was also prejudicial.
To show prejudice, “[t]he defendant must show that there is
a reasonable probability that, but for counsel’s
unprofessional errors, the result of the proceeding would
have been different.” 14 Strickland, 466 U.S. at 694. The
Strickland prejudice standard is “highly demanding.” Shinn
v. Kayer, 592 U.S. 111, 118 (2020) (per curiam) (quoting
Kimmelman, 477 U.S. at 382). Still, defendants are not
required to show that “counsel’s deficient conduct more
likely than not altered the outcome in the case.” Strickland,
466 U.S. at 693. Instead, the likelihood of a different result
must be “substantial, not just conceivable.” Harrington, 562
U.S. at 112.
In making our prejudice determination, we have
thoroughly reviewed the parties’ briefings and carefully
inspected every document in the record. The interrogation
14
Pimentel’s deficient advice occurred during a pre-trial interrogation.
Typically, when ineffective assistance of counsel claims arise from
attorneys’ conduct in pre-trial contexts (like plea negotiations), the
prejudice inquiry turns on whether the result of that proceeding––not the
defendant’s trial––would have been different. Where no trial occurs,
Strickland’s trial-based prejudice inquiry is unduly speculative with
respect to counsel’s pre-trial errors. Garza v. Idaho, 139 S. Ct. 738, 747
(2019) (“[T]here is no disciplined way to ‘accord any “presumption of
reliability” . . . to judicial proceedings that never took place.’” (internal
citation omitted)). Here, however, a trial occurred. Thus, we consider
the impact of Pimentel’s deficient advice on Osorio’s trial because doing
so requires no speculation.
30 USA V. OSORIO-ARELLANES
transcript shows that, but for Pimentel’s advice, Osorio
would not have confessed drug-related information to
authorities. The Indictment, the preliminary jury
instructions, and the prosecution’s opening statement
demonstrate that every charge against Osorio required the
Government to prove his intent to rob drug smugglers
beyond a reasonable doubt. The remaining trial transcripts
show that Osorio’s confession was the Government’s key
evidence on this dispositive factual dispute. 15
Thus, there is a reasonable probability that, absent
Pimentel’s advice, Osorio would not have been convicted of
any of the charges.
i. “But for” Pimentel’s advice, Osorio would not
have confessed drug-related information.
The Government argues that Osorio “has not
demonstrated that he would have refused to provide
statements absent Pimentel’s advice.” 16 However, the
transcript plainly makes that demonstration for him. Before
Pimentel’s advice, Osorio unequivocally refused to admit
his intent to rob drug smugglers and flatly denied any
previous involvement with drugs. The transcript also shows
that these denials were not due to lack of official effort; the
agents deployed all kinds of interrogation techniques to
15
Whenever Osorio’s “confession” is mentioned throughout this
Section, the term only refers to drug-related information he admitted on
Pimentel’s advice.
16
To be sure, before Pimentel’s advice, Osorio confirmed aspects of his
involvement in the shooting. However, Osorio does not allege that he
would not have provided any statements without Pimentel’s advice. The
specific conduct he complained of was that “Pimentel advised and
encouraged” Osorio’s drug-related admissions “based on the erroneous
understanding that it was not a crime to rob drug smugglers.”
USA V. OSORIO-ARELLANES 31
secure Osorio’s confession. Yet, throughout their
questioning, Osorio did not deviate from his story about
dropping off food in the Seep. He said that he had never
been caught with drugs, had never previously robbed drug
smugglers, and did not intend to rob them on the night of
Agent Terry’s death.
The critical shift came after Pimentel’s erroneous advice.
It was only after receiving his attorney’s mistaken
assurances that Osorio began providing the agents with drug-
related information he had previously refused to disclose.
No other intervening event or Government action shook
Osorio’s initial story about the group’s intent to deliver food.
As Agent Dreher put it during the interrogation: “[E]arlier
you told me[] that you . . . didn’t rob the drug runners, right?
And afterwards you confessed.”
We need not speculate about whether Osorio would have
confessed drug-related information to authorities “but for”
Pimentel’s advice. In fact, he did not.
ii. Every charge turned on Osorio’s intent to rob
drug smugglers.
As mentioned above, it is undisputed that the
Government could not secure convictions on any of the
counts without proving the robbery charges beyond a
reasonable doubt. Accordingly, the jury was instructed that
Osorio’s intent to rob drug smugglers was a necessary
element of every crime he was charged with committing,
including felony murder. There is no allegation that these
instructions were incorrect. Thus, we presume that the jury
weighed evidence on this dispositive point during its
deliberations. CSX Transp., Inc. v. Hensley, 556 U.S. 838,
841 (2009) (per curiam) (“[I]n all cases, juries are presumed
to follow the court’s instructions.”).
32 USA V. OSORIO-ARELLANES
Indeed, the trial transcripts underscore the fundamental
importance of Osorio’s intent to rob drug smugglers. Within
the first minute of opening statements, the Government
described Osorio’s group as a “rip crew,” i.e., “individuals
who came to the United States, armed themselves, and were
patrolling in this rural area near Rio Rico looking for drug
smugglers to rob.” The opening statement also quickly
zeroed in on the group’s purpose: “[T]hey were ready for one
thing and one thing alone, to carry out their mission in the
wash that night, and that was to rob drug smugglers.”
The Government’s first presentation to the jury made its
theory of the case perfectly clear: Agent Terry was killed
“while [Osorio] was leading the rip crew through the wash
looking for someone to rob.”
iii. Without Osorio’s confession, there is a
reasonable probability that he would not have
been convicted.
Osorio’s confession was the best evidence the
Government had to prove this dispositive element of its case.
However, that does not render Pimentel’s advice per se
prejudicial. “When,” as here, “a defendant challenges a
conviction, the question is whether there is a reasonable
probability that, absent the errors, the factfinder would have
had a reasonable doubt respecting guilt.” Strickland, 466
U.S. at 695. Generally, “a verdict or conclusion only weakly
supported by the record is more likely to have been affected
by errors than one with overwhelming record support.” Id.
at 696. And “in some instances” even an isolated error by
counsel “can support an ineffective-assistance claim if it is
‘sufficiently egregious and prejudicial.’” Harrington, 562
U.S. at 111 (quoting Murray v. Carrier, 477 U.S. 478, 496
(1986)). Thus, we must consider the impact of Pimentel’s
USA V. OSORIO-ARELLANES 33
advice in light of “the totality of the evidence before the
judge or jury . . . taking the unaffected findings as a given,
and taking due account of the effect of the errors on the
remaining findings.” Strickland, 466 U.S. at 695–96.
We begin with the unaffected findings. Absent the
confession, the Government certainly could have proved the
general circumstances of the shootout. BORTAC Agent
Daniel Herskin testified about monitoring the tripped sensor;
Agents Castano, Fargoza, and Keller testified about the
circumstances of the encounter with the rip crew, and first
responders described the immediate aftermath. Moreover,
BORTAC surveillance equipment took pictures of the
skirmish in real-time, which the Government displayed
throughout trial, and Agent Terwilliger testified about her
crime scene investigation.
Aside from testimony and photographs, the Government
also showed the jury physical evidence from the crime scene,
like AK-47s, shell-casings, unspent ammunition, firearm
lubricant, backpacks, food, water, portable batteries, cell
phone chargers, and other survival supplies. Additionally,
the Government’s forensic pathology expert testified that
Agent Terry’s autopsy strongly suggested his fatal wound
was caused by a single bullet fired from the rip crew’s down-
hill position, and the Government’s firearm and tool marks
expert testified about the investigation he conducted on shell
casings recovered from the scene. The Government’s DNA
evidence also left virtually no doubt that Osorio was present
during the shootout. There was also evidence that Osorio’s
brother Manuel was found injured at the scene, though he
never provided any indication of the group’s intent.
Collectively, this scene-setting evidence could have
established that Agent Terry was killed during the shootout
34 USA V. OSORIO-ARELLANES
by a member of Osorio’s group, which was heavily armed
and outfitted to spend a lot of time outside. Per Strickland,
we take those facts as given. Even still, they were
insufficient to secure Osorio’s convictions: the Government
also had to establish his intent to rob drug smugglers beyond
a reasonable doubt.
The Government saved its best evidence on this point for
last and called Agent Dreher as its final witness at trial. At
the beginning of his testimony, Agent Dreher described the
circumstances of the interrogation and then relayed the
scene-setting information Osorio provided before Pimentel
offered his deficient advice. 17 But that is where the
Government’s unaffected evidence ends: Agent Dreher’s
remaining testimony described the precise admissions
Osorio would not have provided but for Pimentel’s
erroneous advice.
As the direct examination continued, the Government
asked Agent Dreher whether Osorio stated the group’s
purpose during the interrogation, to which he replied,
“[Osorio] said the purpose of the group was to rob other drug
smugglers in the area.” The Government then asked why the
group had targeted the Seep in particular, and Agent Dreher
described Osorio’s admissions about his past experiences
smuggling marijuana through the Seep, his five previous
robberies of drug smugglers, and the payments he received
17
When the Government began to ask about Osorio’s drug-related
admissions, the district court read the jury a limiting instruction pursuant
to Federal Rule of Evidence 404 and noted that to the extent that Agent
Dreher’s testimony mentioned any past criminal conduct, the jury could
only consider it only to establish Osorio’s motive, opportunity,
preparation, plan, knowledge, or absence of mistake. There was no
limiting instruction concerning Osorio’s admissions to the charged
crimes.
USA V. OSORIO-ARELLANES 35
for those efforts. Through this testimony, Agent Dreher
placed the impact of Pimentel’s deficient counsel squarely
before the jury.
During closing arguments, the Government emphasized
the importance of this testimony:
“[Osorio] also told Agent Dreher that he had
successfully robbed drug smugglers on five
prior occasions, and you may consider that
evidence of the prior robberies to show the
defendant’s intent on December 14th, 2010.
He was in Mesquite Seep for one purpose and
one purpose alone, to rob drug smugglers.”
Without Agent Dreher’s testimony, the Government’s
remaining evidence on Osorio’s intent to rob drug smugglers
was relatively speculative and weak. There was the
BORTAC agents’ testimony that they were in the Seep to
apprehend rip crews or “armed bandits,” and that the armed
group’s guns were in ready position when they encountered
the agents. There was one photo from a surveillance camera
showing suspected drug smugglers in the area several days
before the shooting. There was also Agent Jason
Weatherby’s testimony about his experiences in the Seep,
which suggested the area was frequented by drug smugglers,
human traffickers, and rip crews. Agent Weatherby further
testified that rip crews, unlike drug smugglers, were
typically armed. But that was it. The Government did not
introduce any other evidence concerning Osorio’s intent to
rob drug smugglers.
Overall, the unaffected evidence tends to show that drug
smugglers sometimes traveled through the Seep, that rip
crews tended to be armed, and that Osorio’s group traveled
36 USA V. OSORIO-ARELLANES
through the area with guns. This evidence might have been
sufficient to convince the jury of Osorio’s intent to rob drug
smugglers beyond a reasonable doubt. United States v.
Gulino, 588 F.2d 256, 258 n.2 (9th Cir. 1978) (“A defendant
may be proven guilty by either direct or by circumstantial
evidence.”). However, we cannot say that it eliminates any
substantial likelihood of the opposite result. The defense
never conceded Osorio’s guilt, and he never independently
confessed the drug-related information he provided on
Pimentel’s advice. Osorio’s co-defendants’ convictions
were not mentioned, none of his co-conspirators testified
against him, and Osorio did not take the stand at trial.
There is at least a reasonable probability that without
Pimentel’s advice, the case might have come out differently.
Thus, when viewed in light of the cumulative evidence,
Agent Dreher’s testimony establishes prejudice.
Nevertheless, we do not rest our prejudice finding solely on
this accounting of the Government’s trial evidence: The
district court’s post-trial rulings independently place the
issue beyond speculation.
Although the jury ultimately determined Osorio’s guilt,
before the case was submitted, defense counsel moved for
acquittal on the robbery charges based on insufficiency of
the evidence. Specifically, he argued that the Government
could not prove any “substantial step” toward robbery
because it presented no evidence that drug smugglers were
in the Seep on the night of Agent Terry’s death.
In considering this motion, the district court responded
with its assessment of the evidence: “Well, here, though, is
a stated intention. We’re not just walking around with
firearms. Specifically, this case is even stronger if one of the
members says they’re armed in order to rob smugglers in that
USA V. OSORIO-ARELLANES 37
area where they are.” The court then expressly denied the
motion by pointing to the fruits of Pimentel’s deficient
counsel: “[G]iven the experience of these rip crew members,
the personal experience of the defendant, the fact that they
were ready to fire, and to effect this robbery was a substantial
step and, therefore, [] sufficient evidence, of an attempt.”
That is, all but one of the evidentiary bases the district court
used to support its finding flowed directly from admissions
induced by Pimentel’s advice. But for that advice, there is
at least a reasonable probability that the district court’s
sufficiency determination (and thus, the case) would have
come out differently.
Whatever the jury might have thought about the
Government’s unaffected evidence, the district court’s
sufficiency ruling also proves prejudice. On either basis,
Osorio has established his Sixth Amendment claim. 18
18
We recognize that our analysis is not limited to applying a series of
“mechanical rules.” Strickland, 466 U.S. at 696. The “ultimate focus of
inquiry must be on the fundamental fairness of the proceeding whose
result is being challenged.” Id. Specifically, “in every case,” courts must
consider “whether, despite the strong presumption of reliability, the
result of the particular proceeding is unreliable because of a breakdown
in the adversarial process that our system counts on to produce just
results.” Id. There might be some question of what “reliability” means
in this context. Does a proceeding become unreliable when counsel’s
errors effectively circumvent the adversarial testing process that we rely
on to produce just results? Or can a court deem that proceeding’s
outcome reliable if it is sufficiently certain that the result is just, i.e., that
it fairly assigns blame? It seems the Supreme Court favors the former
conception: “[I]f counsel entirely fails to subject the prosecution’s case
to meaningful adversarial testing, then there has been a denial of Sixth
Amendment rights that makes the adversary process itself presumptively
unreliable.” Cronic, 466 U.S. at 659; see also Kimmelman, 477 U.S. at
380 (“[W]e have never intimated that the right to counsel is conditioned
upon actual innocence.”). Regardless of whether Osorio’s confession
38 USA V. OSORIO-ARELLANES
III. The Fifth Amendment.
Because Osorio has established his Sixth Amendment
claim, we need not reach his Fifth Amendment claim.
Nevertheless, we briefly address the Government’s position
that Osorio’s Sixth Amendment claim rises and falls with his
Fifth Amendment claim. For the sake of argument, we will
assume: (1) Osorio waived his Fifth Amendment rights, and
(2) no underlying Fifth Amendment violation occurred.
Neither assumption bars Osorio’s Sixth Amendment claim.
First, the waiver point is immaterial. The Miranda
warnings are specifically designed “[t]o safeguard the
uncounseled individual’s Fifth Amendment privilege
against self-incrimination.” Keohane, 516 U.S. at 107
(emphasis added). Thus, in cases involving Fifth
Amendment waivers’ impact on Sixth Amendment claims,
the key question is whether a defendant’s uncounseled
confession is admissible because the Miranda warnings
adequately conveyed his Sixth Amendment right to an
attorney during an interrogation. 19
was “reliable”––indeed, no one alleges it was false––Pimentel’s
deficient advice induced admissions that provided essential elements of
the Government’s case, which deprived Osorio of “the guiding hand that
the Constitution guarantees.” Cronic, 466 U.S. at 649; see also
Kimmelman, 477 U.S. at 379, 391 (determining that on a sufficient
showing of prejudice, an attorney’s failure to suppress “reliable” but
damning evidence, could amount to ineffective assistance of counsel).
Indeed, given the dispositive impact of Pimentel’s advice, the defense
did not call a single witness or present any exhibits.
19
Montejo, 556 U.S. at 791 (“[E]veryone agrees that absent a valid
waiver, Montejo was entitled to a lawyer during the interrogation.”); see
Maryland v. Shatzer, 559 U.S. 98, 102 (2010) (“At no point during the
interrogation did Shatzer request to speak with an attorney or refer to his
prior refusal to answer questions without one.”).
USA V. OSORIO-ARELLANES 39
That question is simply inapposite when a defendant
invokes his right to counsel, obtains counsel’s physical
presence during an interrogation, and relies on counsel’s
advice throughout questioning. This defendant has not
waived his right to counsel––he has plainly exercised it. We
are aware of no authority suggesting that Fifth Amendment
waivers bar subsequent Sixth Amendment claims when a
defendant’s attorney was physically present during an
interrogation and actively encouraged his client’s admission.
Second, the Government suggests Osorio’s Sixth
Amendment claim must fail because it is actually a Fifth
Amendment claim cloaked in Strickland dress. The Sixth
Amendment right to effective assistance of counsel and the
Fifth Amendment right against self-incrimination support
distinct constitutional claims that promote entirely separate
interests. 20 Henry, 447 U.S. at 273 (rejecting a line of
argument that sought “to infuse Fifth Amendment concerns
against compelled self-incrimination into the Sixth
Amendment protection of the right to the assistance of
counsel”). Osorio’s Sixth Amendment claim is not invalid
because it arises from a fact pattern that also implicates Fifth
Amendment interests. See Patterson, 487 U.S. at 297
(“While our cases have recognized a ‘difference’ between
the Fifth Amendment and Sixth Amendment rights to
counsel, and the ‘policies’ behind these constitutional
guarantees, we have never suggested that one right is
20
Compare Rhode Island v. Innis, 446 U.S. 291, 297 (1980) (noting that
Miranda warnings are necessary in “certain procedural safeguards are
necessary to protect a defendant’s Fifth and Fourteenth Amendment
privilege against compulsory self-incrimination”), with Strickland, 466
U.S. at 689 (“[T]he purpose of the effective assistance guarantee of the
Sixth Amendment . . . is simply to ensure that criminal defendants
receive a fair trial.”).
40 USA V. OSORIO-ARELLANES
‘superior’ or ‘greater’ than the other.”). These constitutional
protections do not collapse based on the underlying factual
circumstances. 21 See Henry, 447 U.S. at 272 (holding that
“Fifth Amendment claims made in” cases where undercover
officers obtain incriminating statements before charges are
filed “are not relevant to the inquiry under the Sixth
Amendment”).
The absence of a Fifth Amendment violation does not
bar Osorio’s Sixth Amendment claim.
CONCLUSION
Osorio’s jailhouse confession was admitted in violation
of his Sixth Amendment rights. His convictions and
sentences are set aside, and his case remanded to the district
court for further proceedings consistent with this opinion.
Importantly, our holding does not decide Osorio’s
ultimate responsibility for his actions. The Government can
still retry this case. Nevertheless, his direct appeal reaffirms
the potency of our Constitution’s procedural protections for
criminal defendants, which “are granted to the innocent and
the guilty alike.” Kimmelman, 477 U.S. at 380. Due
process, including the right to effective assistance of
counsel, is what separates America from authoritarian
regimes around the world. See Gideon v. Wainwright, 372
U.S. 335, 344 (1963) (“The right of one charged with crime
to counsel may not be deemed fundamental and essential to
fair trials in some countries, but it is in ours.”).
21
See also Estelle v. Smith, 451 U.S. 454, 470 n.14 (1981) (“[W]e are
not concerned in this case with the limited right to the appointment and
presence of counsel recognized as a Fifth Amendment safeguard in
Miranda . . . Rather, the issue before us is whether a defendant’s Sixth
Amendment right to the assistance of counsel is abridged.”).
USA V. OSORIO-ARELLANES 41
VACATED, REVERSED, AND REMANDED.
HURWITZ, Circuit Judge, dissenting:
Before federal agents began questioning Heraclio
Osorio-Arellanes in a Mexican prison, he received a
Miranda warning in Spanish designed for foreign
interrogations. The warning expressly informed him that he
was entitled to consult with an attorney trained in the United
States before answering questions, and there could be some
delay in providing such an attorney. 1 He does not contest
1
The warning provided to Osario, entitled “Notification of the Rights of
Suspects Under Foreign Custody,” provided:
We are representatives of the United States
government. Although we may not be in the United
States of America, the laws of the United States
provide you with certain rights when dealing with us.
Before we pose any questions to you, you must
understand your rights.
You have the right to remain silent. Even if you have
already spoken with other persons, you do not have to
speak with us at this time.
Anything you say can be utilized against you in court.
You have the right to speak with an attorney so that he
may counsel you before we pose any questions to you.
You have the right to have an attorney present during
your questioning.
If you do not have the means to pay for an attorney,
you have the right to have one be designated to you
before any question is posed to you, if you so wish.
42 USA V. OSORIO-ARELLANES
that he understood the warning yet opted to answer questions
from the agents after a brief consultation with a Mexican
lawyer, whom he identified as “my attorney.” After
receiving the advice at the center of this appeal from that
attorney, Osorio made inculpatory statements concerning the
murder of Customs and Border Patrol Agent Brian Terry.
Those statements were introduced at his trial, and he was
convicted.
The majority today overturns that conviction. It does not
find Osorio’s confession involuntary nor any Miranda
violation. Rather, the majority holds that the conviction
cannot stand because Osorio received ineffective assistance
from his chosen Mexican lawyer during the interrogation.
In doing so, the majority plows significant new doctrinal
ground. Were we compelled to decide the issue of
ineffective assistance on direct appeal, I might reach the
same conclusion as the majority. But we labor under no such
compulsion. The Supreme Court has counseled that “few
[ineffective-assistance] claims will be capable of resolution
on direct appeal.” Massaro v. United States, 538 U.S. 500,
507 (2003); see also United States v. McKenna, 327 F.3d
830, 845 (9th Cir. 2003) (stating the general rule that
ineffective assistance of counsel claims are “generally
inappropriate on direct appeal.”).
However, our ability to provide you an attorney at this
time can be limited by the decisions that local
authorities may have taken or by the availability of an
attorney trained in the United States of America. If you
decide to answer questions at this time, in the absence
of an attorney, you have the right to stop answering
them at any time.
USA V. OSORIO-ARELLANES 43
The majority nonetheless decides to take up the
ineffective assistance of counsel claim on direct appeal
because it concludes that this is a case “(1) where the record
on appeal is sufficiently developed to permit determination
of the issue” and “(2) where the legal representation is so
inadequate that it obviously denies a defendant his Sixth
Amendment right to counsel.” Majority Opinion at 13-14
(quoting United States v. Jeronimo, 398 F.3d 1149, 1156
(9th Cir. 2005)). But, this is plainly a discretionary decision,
and in my view, “collateral review provides the appropriate
forum for [Osorio’s] ineffective assistance of counsel
claim.” United States v. Miskinis, 966 F.2d 1263, 1269 (9th
Cir. 1992).
“The customary procedure for challenging the
effectiveness of defense counsel in a federal criminal trial is
by collateral attack on the conviction under 28 U.S.C.
§ 2255. This is so because usually such a claim cannot be
advanced without the development of facts outside the
original record.” United States v. Birges, 723 F.2d 666, 670
(9th Cir. 1984) (cleaned up). On the few occasions when we
have found a record sufficiently developed to depart from
this customary practice, that record was made in a judicial
proceeding. See, e.g., United States v. Alferahin, 433 F.3d
1148, 1160 n.6 (9th Cir. 2006); United States v. Swanson,
943 F.2d 1070, 1072 (9th Cir. 1991); United States v.
Hernandez, 403 F. App’x 281, 282 (9th Cir. 2010). In
contrast, the majority today relies heavily on the translation
of Osorio’s out-of court interrogation. The legend that
accompanies that translation, however, carries a significant
disclaimer: “The quality of the recording is not optimal and
there is no video available so it is sometimes difficult to
distinguish between speakers.” The transcript includes over
one hundred “unintelligible” markings.
44 USA V. OSORIO-ARELLANES
Even if the transcript is properly considered, it contains
no statement by Osorio that the Mexican attorney’s advice
caused him to make the relevant admissions. Although that
is a reasonable inference from the transcript, it is only an
inference; neither Osorio nor his Mexican attorney ever so
stated, either in the transcript or anywhere else under oath in
these proceedings and the arguments of his present counsel
are not evidence. In my view, we would benefit from factual
development of the record—and the findings of a habeas
court—before reaching this conclusion. See United States v.
Miskinis, 966 F.2d 1263, 1269 (9th Cir. 1992) (“The issue
that a district court would be required to determine on
collateral review is whether Miskinis would have taken
advantage of an advice of counsel defense but for Mitchell’s
representation of him at the trial.”). Before vacating the
conviction, we should hear from Osorio and, if he claims that
the advice led to his relevant admissions, have that testimony
subjected to cross-examination. See United States v. Rivera-
Sanchez, 222 F.3d 1057, 1060 (9th Cir. 2000) (finding
record sufficiently developed “because the district court held
a hearing” at which both the defendant and counsel testified
about counsel’s alleged ineffectiveness).
In addition, why Pimentel showed up at the prison
(apparently without being contacted by Osorio), who hired
him, and what he told Osorio during their pre-interrogation
conference are, as the district judge aptly noted, “facts that I
don’t have.” Nor do we. A more-developed record might
well support the government’s contention that although
Osorio knew that he had the choice to wait for “an attorney
trained in the United States,” he knowingly decided to
proceed with one whom he knew was not. If this were the
case, the government’s argument that Osorio ostensibly
USA V. OSORIO-ARELLANES 45
waived his right to effective representation of United States-
trained counsel might need to be reevaluated in a new light.
It may well be that the result reached by the majority
today would not be altered by a 28 U.S.C. § 2255 proceeding
in the district court. But before vacating the conviction of a
defendant who voluntarily admitted that he participated in
the murder of a federal agent, I would prefer to at least make
an attempt to have the “facts we don’t have.” I therefore
would affirm Osorio’s conviction and require him to make
his case for ineffective assistance of counsel in the first
instance in the district court through a § 2255 motion. I
respectfully dissent.
Plain English Summary
FOR PUBLICATION UNITED STATES COURT OF APPEALS FOR THE NINTH CIRCUIT UNITED STATES OF AMERICA, No.
Key Points
01FOR PUBLICATION UNITED STATES COURT OF APPEALS FOR THE NINTH CIRCUIT UNITED STATES OF AMERICA, No.
03Bury, District Judge, Presiding Argued and Submitted February 13, 2024 University of Arizona College of Law (Tucson) Filed August 9, 2024 Before: Michael Daly Hawkins, Andrew D.
04OSORIO-ARELLANES SUMMARY * Criminal Law The panel reversed the district court’s order reconsidering its suppression of a confession by Heraclio Osorio-Arellanes (“Osorio”), vacated his convictions and sentences, and remanded for further pro
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