FOR PUBLICATION

UNITED STATES COURT OF APPEALS

FOR THE NINTH CIRCUIT

UNITED STATES OF AMERICA, 

Plaintiff-Appellee, 

 v. 

HERACLIO OSORIO-ARELLANES, 

AKA Laco, 

Defendant-Appellant.

No. 20-10003 

D.C. No. 

4:11-cr-00150-

DCB-LCK-4 

OPINION

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 selfincrimination 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 OsorioArellanes (“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 selfincrimination 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 fiftyseven 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: firstand 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 codefendants). 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 selfincrimination 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 selfproduced 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 

10 Dreher: “I just handed this to you and to the gentleman, your attorney, 

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 drugrelated 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 downhill 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. RiveraSanchez, 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 Statestrained 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.