United States v. Sierra-Estrada

FILED
United States Court of Appeals
Tenth Circuit

UNITED STATES CO URT O F APPEALS
October 1, 2007
Elisabeth A. Shumaker
TENTH CIRCUIT Clerk of Court

U N ITED STA TES O F A M ER ICA,

Plaintiff-Appellee/ Nos. 05-4086, 05-4117
Cross-Appellant,
v. (D. Utah)
ROBERTO SIERRA-ESTRADA, a/k/a (D.C. No. 2:02-CR-126-JTG)
Chorizo,

Defendant-Appellant/
Cross-A ppellee.

OR D ER AND JUDGM ENT *

Before KELLY, A LA RC ÓN, ** and HENRY, Circuit Judges.

A jury convicted Roberto Sierra-Estrada of conspiring to distribute

methamphetamine in violation of 21 U.S.C. §§ 841(a)(1) and 846. The district

court sentenced him to the mandatory minimum ten years’ imprisonment. M r.

*
This order and judgment is not binding precedent except under the
doctrines of law of the case, res judicata and collateral estoppel. It may be cited,
however, for its persuasive value consistent with Fed. R. App. P. 32.1 and 10th
Cir. R. 32.1.
**
The Honorable Arthur L. Alarcón , Senior Circuit Judge, United States
Court of Appeals for the Ninth Circuit, sitting by designation.
Sierra-Estrada appeals the district court’s denial of (1) his motion to suppress

inculpatory statements he made to Federal Bureau of Investigation (FBI) agents,

(2) his motion to dismiss the indictment based on the government’s deportation of

a material witness, and (3) his motion for a mistrial based on prosecutorial

misconduct during the rebuttal portion of the government’s closing argument.

The government cross-appeals M r. Sierra-Estrada’s sentence, arguing that the

district court erred as a matter of law when it refused to impose a twenty-year

mandatory minimum sentence under § 21 U .S.C. § 841(b)(1)(A). W e exercise

jurisdiction under 28 U.S.C. § 1291, and we affirm.

I. BACKGROUND

A . F ACTUAL B ACKGROUND

On M arch 7, 2001, the FBI received a tip from a confidential informant that

M r. Sierra-Estrada and another individual, later identified as Gabino Sanchez,

were planning to transport methamphetamine to Kansas City. Later that day, FBI

agents set up surveillance outside M r. Sierra-Estrada’s apartment near Salt Lake

City. During the surveillance, an FBI agent observed a black Lincoln Continental

matching information given by the informant and saw M r. Sierra-Estrada carry a

red and white cooler into the apartment. W hen M r. Sanchez left the apartment by

himself in the Lincoln, the FBI notified the Utah Highway Patrol.

Utah Highway Patrol Troopers stopped M r. Sanchez’s vehicle for an

equipment violation. During the stop, a drug detection dog indicated the presence

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of drugs in a red and white cooler located on the passenger seat of M r. Sanchez’s

vehicle. The officers discovered two packages containing approximately 382

grams of methamphetamine in a secret compartment created in the cooler’s

Styrofoam lining and arrested M r. Sanchez.

Approximately a week-and-a-half after M r. Sanchez’s arrest, the FBI

intercepted a telephone call between M r. Sierra-Estrada and Leonel Acevedo-

Torres, a suspected drug dealer who was the subject of a court-ordered wiretap in

Riverside County, California. During the call, which was translated from Spanish

into English by the FBI, M r. Sierra-Estrada told M r. Acevedo-Torres, in code,

about M r. Sanchez’s arrest and the large amount of methamphetamine that had

been confiscated by law enforcement. M r. Sierra-Estrada further stated that, due

in part to M r. Sanchez’s arrest, he would be unable to pay for drugs previously

advanced by M r. Acevedo-Torres.

On April 18, 2001, M r. Sanchez was indicted for possession of

m etham phetamine w ith intent to distribute. The FBI subsequently conducted tw o

interviews with him, the contents of which were memorialized in two FBI

investigation reports (“FBI 302s”). Prior to the first interview, an FBI agent

discovered a note in M r. Sanchez’s vehicle bearing M r. Sierra-Estrada’s cell

phone number.

During the initial interview, M r. Sanchez admitted he was transporting the

methamphetamine seized by the Utah Highway Patrol to Kansas City. He did not,

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however, mention M r. Sierra-Estrada. He instead stated that he had traveled to

the apartment complex where M r. Sierra-Estrada lived to meet a man named

“Pedro,” who was not involved with his transportation of the methamphetamine.

W hen the interview ing agents showed him a picture of M r. Sierra-Estrada, M r.

Sanchez indicated that he had met him at a dance in M exico but did not know his

name or current whereabouts.

During the second interview , M r. Sanchez again did not mention M r.

Sierra-Estrada. He provided that he had stopped at the apartment where M r.

Sierra-Estrada resided to better conceal the methamphetamine in a cooler he had

purchased. According to M r. Sanchez, he did not know the individuals at the

apartment, and they were unaware he was carrying methamphetamine.

On November 8, 2001, M r. Sanchez pleaded guilty to possession of

methamphetamine with intent to distribute. In February 2002, he was sentenced

to thirty-four months’ imprisonment.

On February 28, 2002, the Immigration and Naturalization Service notified

the FBI that it had taken M r. Sierra-Estrada into custody on unrelated charges and

that he was being held at the Summit County Jail. Because the FBI had been

planning to arrest M r. Sierra-Estrada based on “information that he was getting

ready to transport a shipment of methamphetamine to South Dakota,” it made

arrangements to speak with him. Supp. Rec. vol. II, at 9.

On M arch 1, 2002, at approximately 7:30 p.m., two FBI agents met with

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M r. Sierra-Estrada in a room at the Summit County Jail. At the outset of the

interview, which was conducted through an FBI Spanish-language interpreter, the

agents advised M r. Sierra-Estrada of his rights under M iranda v. Arizona, 384

U.S. 436 (1966), and asked if he w anted to speak with them. In response, M r.

Sierra-Estrada asked, “I w onder if I could have access to a law yer. Is it possible

if I don’t have money?” Supp. Rec. vol. II, at 14. The agents replied that “it was

possible, all he had to do was ask for one, one would be provided to him. W e

would not interview him at that time. W e would wait until a later time to do the

interview.” Id.

At approximately 7:42 p.m., the agents presented M r. Sierra-Estrada with a

Spanish-language “advice of rights” form explaining his M iranda rights. The

form also advised M r. Sierra-Estrada that he would waive his rights by signing it.

After reading the form to himself, M r. Sierra-Estrada inquired whether “he could

get a lawyer in the future if he wanted one.” Id. at 15. In response, one of the

agents stated, “sure you can, as soon as you ask for one.” Id. M r. Sierra-Estrada

then asked about the type of deal and sentence he would receive if he cooperated.

The agents explained that they lacked the authority to discuss such matters, but

would inform the prosecuting attorneys of all the information he provided. The

agents also addressed M r. Sierra-Estrada’s concerns regarding the FBI’s ability to

ensure his safety if he cooperated.

M r. Sierra-Estrada continued to ask the agents questions for around 35 to

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40 minutes. During this time, M r. Sierra-Estrada also re-read the advice of rights

form, and was told by the agents “around five” times that the interview would

stop as soon as he asked for an attorney. Id. at 17. At some point, M r. Sierra-

Estrada inquired whether “he could start talking and stop talking later.” Id. at 18.

The agents told him he could. At approximately 8:17 p.m., M r. Sierra-Estrada

told the agents he wanted to talk to them and signed the advice of rights form.

After doing so, M r. Sierra-Estrada proceeded to confess to conspiring to

distribute the methamphetamine found in M r. Sanchez’s car. Specifically, he told

the agents that he created the hidden compartment inside the cooler in which the

methamphetamine was discovered in exchange for $500 from M r. Sanchez, that

he placed the methamphetamine in the cooler, that he handed the cooler to M r.

Sanchez, and that he told M r. Sanchez, who was nervous, to “take the

methamphetamine and not to be afraid.” Id. vol. VI, at 58. M r. Sierra-Estrada

also admitted that he was the person speaking to M r. Acevedo-Torres on the

intercepted phone call and explained the contents of the conversation to the

agents.

On M arch 4, M r. Sierra-Estrada spoke with the FBI agents for a second

time. Once again, M r. Sierra-Estrada was apprised of his M iranda rights through

an interpreter and he signed a Spanish-language advice of rights form. During

this interview, M r. Sierra-Estrada confirmed his involvement in the transportation

and distribution of illegal narcotics for many years.

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 B. P ROCEDURAL H ISTORY

On M arch 2, 2002, M r. Sierra-Estrada was indicted for conspiracy to

distribute the methamphetamine hidden insider the cooler in M r. Sanchez’s

vehicle.

Prior to trial, he filed a motion to suppress the inculpatory statements he

made during his FBI interview s. He argued that he had effectively invoked his

right to counsel at the outset of his initial interview and, consequently, the agents

should have stopped their questioning until an attorney was provided.

On July 2, 2003, after holding an evidentiary hearing, the district court

denied M r. Sierra-Estrada’s motion to suppress, stating that:

[u]nder the totality of the circumstances, . . . I am convinced that this
was not an invocation of the right to counsel. It was simply a matter of
simple, careful questioning, all having to do with what m ight be
provided in the future. I am satisfied that the answers . . . given by
Agent Ross were appropriate, they w ere clear, and there is no doubt
about the fact that if this defendant had asked for a lawyer at any time,
he would have had one. Nothing prior to his execution of the document
having to do with his rights and going ahead with questioning – by the
time he had signed that he had a clear understanding that at any time he
might invoke and ask for a law yer. H e never did. And this is a matter
of the agents simply being careful. The time, 47 minutes, reflects not
only careful handling of the matter, it reflects the necessity of
interpretation of consideration and being sure that he understood the
document. He looked at the document. He read it. H e had it read to
him. It was in Spanish. I am satisfied that this is an appropriate
procedure and I am going to deny the motion to suppress the custodial
statements, and that motion is denied.

Id. vol. III, at 13.

On August 15, 2003, M r. Sierra-Estrada’s trial counsel moved the district

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court for authorization to travel to the prison where M r. Sanchez was incarcerated

in order to interview him. On August 25, 2003, the district court granted trial

counsel’s motion. Three days earlier, however, unbeknownst to trial counsel, the

Bureau of Prisons released M r. Sanchez from prison and turned him over to

immigration officials for deportation. A memorandum from the Bureau of Prisons

to the FBI indicated that M r. Sanchez had been given 334 days of credit for time

served in federal custody prior to sentencing and had completed his 34-month

sentence on August 22, 2003.

On September 8, 2003, trial counsel moved for a continuance in order to

secure M r. Sanchez’s presence at trial so that he could testify, and the government

joined in the motion. The government also provided trial counsel for the first

time with the FBI 302s from the two interviews it conducted with M r. Sanchez.

Inexplicably, these reports were not contained in the government’s previous

discovery disclosures. The district court granted M r. Sierra-Estrada’s motion.

An investigator for M r. Sierra-Estrada eventually contacted M r. Sanchez in

M exico via telephone. M r. Sanchez, however, was unwilling to speak about the

case. The FBI then contacted M r. Sanchez, but he indicated that he was unwilling

to testify for M r. Sierra-Estrada. He also refused to allow the government or trial

counsel to interview him in M exico.

M r. Sierra-Estrada moved to dismiss the indictment because M r. Sanchez’s

deportation violated his Fifth Amendment right to due process and his Sixth

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Amendment right to compulsory process. At a hearing on this motion, M r. Sierra-

Estrada suggested that, rather than dismissing the case, the district court could

admit the previously undisclosed FBI 302 reports without regard to hearsay or

foundation objections. The government agreed that it would not object to the

admission of the FBI 302s at trial.

The district court ruled as follow s:

The motion to dismiss is denied subject to the discussion that we’ve had
about an agreement that there is no bad faith in the sense of the United
States Attorney’s office having caused in any w ay the deportation.
W hat might be said about the failure of an FBI agent to have revealed
those 302 statements [prior to the September 8, 2003, hearing] is still
a possibility of something that might be raised in cross-exam ination.
But the most significant thing that could be raised is what was said by
M r. Sanchez in the two interviews with the FBI agent and that can come
in. And with that understanding and the lack of bad faith on the part of
the United States Attorney’s Office, we’ll go ahead and deny the motion
subject to those conditions.

Id. vol. IV, at 34-35.

During a two-day trial, the government introduced evidence regarding (1)

M r. Sierra-Estrada’s custodial statements, (2) the intercepted phone call between

M r. Sierra-Estrada and M r. Acevedo-Torres, (3) the note from M r. Sanchez’s

vehicle containing M r. Sierra-Estrada’s cell phone number, (4) the seizure of

methamphetamine from the cooler in M r. Sanchez’s vehicle, and (5) testimony

that M r. Sierra-Estrada was seen outside of his apartment carrying a similar

cooler. The FBI 302s were also admitted as evidence and the jury heard some

additional testimony regarding M r. Sanchez’s statements. During the rebuttal

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portion of the government’s closing argument, the prosecutor stated the jury had a

duty to be a part of the “shining city on the hill” described by President Reagan

by connoting M r. Sierra-Estrada as an unwelcome transgressor. Id. vol. VII, at

27. 1

Defense counsel promptly objected. The district court overruled the

objection stating, “It’s argument. The jury can evaluate that. Go ahead.” Id. at

28. Follow ing closing arguments, the court instructed the jury that “[s]tatements,

objections and arguments of counsel are not evidence.” Id. at 33.

After the case w as submitted to the jury, M r. Sierra-Estrada moved for a

mistrial based on the prosecutor’s “shining city on the hill” statement. The

district court denied the motion, and the jury convicted M r. Sierra-Estrada of

conspiracy to distribute methamphetamine in violation of 21 U.S.C. §§ 841(a)(1)

and 846.

C. S ENTENCING

Following M r. Sierra-Estrada’s conviction, the United States Probation

Office prepared a presentence investigation report (“PSR”). The PSR noted that

M r. Sierra-Estrada was subject to a mandatory minimum sentence of 10 years and

a maximum sentence of life in prison. See 21 U.S.C. § 841(b)(1)(A). Because

M r. Sierra-Estrada had an offense level of 34 and a criminal history category of I,

1
W e set forth the prosecutor’s statement in more detail below.

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his recommended Sentencing Guidelines range w as 151 to 188 months. However,

because the government had filed an information prior to trial pursuant to 21

U.S.C. § 851 alleging that M r. Sierra-Estrada w as subject to a 20-year mandatory

minimum sentence based on a prior California felony drug conviction, the PSR

stated that the Guideline sentence was 20 years’ imprisonment. See 21 U.S.C. §

841(b)(1)(A).

M r. Sierra-Estrada objected to the 20-year enhanced mandatory minimum,

arguing that the government failed to prove beyond a reasonable doubt that his

prior California conviction was a felony. See 21 U.S.C. § 851(c) (stating that if a

defendant “denies any allegation of the information of prior conviction . . . . the

United States attorney shall have the burden of proof beyond a reasonable doubt

on any issue of fact”). The district court held an evidentiary hearing, at which the

government introduced certified copies of court records indicating that M r.

Sierra-Estrada had pleaded guilty to possessing heroin in violation of Cal. Health

& Safety Code § 11352. These court records included: (1) a complaint filed in

Riverside Superior Court, charging M r. Sierra-Estrada with violating Cal. Health

& Safety Code §§ 11351 (Counts I & III) and 11352 (Counts II and IV); (2) a

criminal information, charging M r. Sierra-Estrada with two counts of violating §

11352; (3) a copy of the docket, showing that M r. Sierra-Estrada pleaded guilty to

§ 11352 and was granted 36 months probation; and (4) a disposition sheet

purporting to show a history of M r. Sierra-Estrada’s case from arrest through

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sentencing. These documents indicated that the offense of conviction was a

felony.

Although M r. Sierra-Estrada conceded that possession of heroin w as a

felony, he argued the government failed to prove that conviction beyond a

reasonable doubt. For support, M r. Sierra-Estrada introduced two probation

reports, both w ith the w ord “felony” crossed out and granting probation to M r.

Sierra-Estrada. He argued these documents created an ambiguity as to whether he

was convicted of a felony. The government offered no explanation why the w ord

“felony” was crossed out.

At sentencing, the district declined to apply the enhanced mandatory

minium. The court concluded that the recommended Guidelines range “overstated

the seriousness of this” and sentenced M r. Sierra-Estrada to the mandatory

minimum ten years’ imprisonment. Id. at 12.

Both parties filed timely notices of appeal.

II. DISCUSSION

On appeal, M r. Sierra-Estrada challenges the district court’s denial of (1)

his motion to suppress the inculpatory statements he made during his FBI

interview s, (2) his motion to dismiss the indictment, and (3) his motion for a

mistrial. W e address these challenges in turn.

A. I NVOCATION OF R IGHT TO C OUNSEL

M r. Sierra-Estrada argues the district court erred in denying his motion to

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suppress the inculpatory statements he made to the FBI because he clearly

invoked his right to counsel during his initial FBI interview. In reviewing the

denial of a motion to suppress, we examine the district court’s factual findings for

clear error, its legal determinations de novo, and we view the evidence in the light

most favorable to the government. United States v. M cKerrell, 491 F.3d 1221,

1224-25 (10th Cir. 2007). Accordingly, in assessing whether the district court

properly determined that M r. Sierra-Estrada failed to invoke the right to counsel,

we accept the district court’s factual findings regarding the words M r. Sierra-

Estrada used unless they are clearly erroneous. United States v. M arch, 999 F.2d

456, 459 (10th Cir. 1993). W e review de novo, however, “[w]hether those words

actually invoked the right to counsel.” Id. (internal quotations and citation

omitted).

Under M iranda, law enforcement officers m ust advise a suspect who is

subjected to custodial interrogation that he has the right to remain silent, that

statements can be used against him, that he has the right to counsel, and that he

has the right to have counsel appointed. 384 U.S. at 467-73. Although a suspect

may waive those rights, all questioning must stop if the suspect requests an

attorney at any time during the custodial interrogation. Edwards v. Arizona, 451

U.S. 477, 484-85 (1981). Questioning may only resume if a lawyer has been

provided or the suspect himself reinitiates communication with law enforcement.

Id.

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 In D avis v. United States, 512 U.S. 452, 458-59 (1994), the Supreme Court

set forth the standard for evaluating whether a suspect has invoked the right to

counsel during a custodial interrogation. Under Davis, a suspect only invokes

that right by “articulat[ing] his desire to have counsel present sufficiently clearly

that a reasonable police officer in the circumstances would understand the

statement to be a request for an attorney.” 512 U.S. at 459. “[I]f a suspect makes

a reference to an attorney that is ambiguous or equivocal in that a reasonable

officer in light of the circumstances would have understood only that the suspect

might be invoking the right to counsel,” law enforcement questioning need not

cease. Id. (emphasis in original). Furthermore, when a suspect’s request is

ambiguous or equivocal, law enforcement officers are not constitutionally

required to clarify that statement, though it may be “good police practice” to do

so. Id. at 461.

In application, these principles indicate that statements contemplating the

invocation of the right to counsel are not sufficient to actually invoke the right to

counsel. See id. at 462 (holding that the defendant failed to unambiguously

request counsel when he stated, “M aybe I should talk to a lawyer”); United States

v. Zamora, 222 F.3d 756, 765-66 (10th Cir. 2000) (defendant’s statement that “I

might want to talk to an attorney” was not a clear invocation); Burket v.

Angelone, 208 F.3d 172, 198 (4th Cir. 2000) (holding “I think I need a law yer”

was not a clear invocation); Diaz v. Senkowski, 76 F.3d 61, 63-65 (2d Cir. 1996)

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(holding “I think I want a lawyer” and “Do you think I need a lawyer?” were not

clear invocations). Rather, to invoke the right to counsel, a statement must

contain “the clear implication of a present desire to consult with counsel.” Lord

v. Duckworth, 29 F.3d 1216, 1221 (7th Cir. 1994). Compare United States v.

Johnson, 400 F.3d 187, 197 (4th Cir. 2005) (holding that answ ering “no” in

response to “Do you want to make a statement at this time without a lawyer?” was

a clear invocation) with United States v. Doe, 170 F.3d 1162, 1166 (9th Cir.

1999) (holding that “W hat time w ill I see a law yer?” w as not a clear invocation).

Applying the Supreme Court’s decision in Davis to his case, M r. Sierra-

Estrada first contends he unambiguously invoked his right to counsel at the outset

of his first FBI interview when he inquired, “I w onder if I could have a lawyer.

Is it possible if I don’t have money?” Supp. Rec. vol. II, at 14. W e disagree.

From an objective standpoint, this statement was ambiguous at best because it

does not suggest a present desire to speak with counsel. Instead, the plain

language suggests that M r. Sierra-Estrada was inquiring into whether his right to

an attorney was contingent upon his ability to pay for one. See Lord, 29 F.3d at

1220-21 (holding that defendant’s statement that “I can’t afford a law yer but is

there anyway I can get one?” was not a clear invocation of the right to counsel).

This interpretation is particularly reasonable in light of M r. Sierra-Estrada’s

failure to request counsel or ask the agents to stop the interview after the agents

responded to his statement by explaining he would have an attorney as soon as he

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“ask[ed] for one.” Supp. Rec. vol. II, at 17.

Alternatively, M r. Sierra-Estrada contends that a reasonable officer would

have understood him to have requested counsel prior to waiving his

M iranda rights because he referenced an attorney multiple times over the forty-

seven m inutes preceding his waiver, he had no understanding of A merican laws,

and he could not speak English. But an examination of the circumstances

surrounding M r. Sierra-Estrada’s w aiver indicates just the opposite. First, M r.

Sierra-Estrada’s additional inquires as to whether “he could get a lawyer in the

future if he w anted one” and “start talking and stop talking later,” like his inquiry

at the outset of his interview , suggest that he was seeking to clarify his right to

counsel, not actually invoking it. Supp. Rec. vol. II, at 18, 45; see United States

v. Uribe-G alindo, 990 F.2d 522, 524, 526-27 (10th Cir. 1992) (holding that a

defendant asking “whether he could have an attorney later on if he asked for one”

did not invoke the right to counsel). Second, there is no evidence that M r. Sierra-

Estrada’s request for counsel was lost in translation; an FBI interpreter was

present throughout the interview and M r. Sierra-Estrada agreed both orally and in

writing to waive his M iranda rights after being advised of those rights in his

native language. Given this evidence, we agree with the district court that the

amount of time – forty-seven minutes – leading up to M r. Sierra-Estrada’s waiver

of his M iranda rights, “reflects . . . careful handling of the matter” by the FBI.

Supp. Rec. vol. III, at 13. Accordingly, M r. Sierra-Estrada did not invoke his

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right to counsel.

B. D EPORTATION OF G ABINO S ANCHEZ

M r. Sierra-Estrada also contends the district court erred in denying his

motion to dismiss the indictment because his Fifth Amendment due process rights

and his Sixth Amendment compulsory process rights were violated when the

government deported M r. Sanchez from the U nited States. At trial, the defense

theory was essentially that M r. Sierra-Estrada had no knowledge of the

methamphetamine discovered in M r. Sanchez’s car. M r. Sierra-Estrada contends

M r. Sanchez would have corroborated this claim because M r. Sanchez did not

implicate M r. Sierra-Estrada during his FBI interviews.

A district court’s refusal to dismiss to an indictment is reviewed for an

abuse of discretion. United States v. Alcaraz-Arellano, 441 F.3d 1252, 1265

(10th Cir. 2006). A district court abuses its discretion if its decision “is based

upon an error of law or a clearly erroneous finding of fact.” U nited States v. Lin

Lyn Trading, Ltd., 149 F.3d 1112, 1117 (10th Cir. 1998) (internal quotation

marks omitted).

To obtain relief from the deportation of a potentially favorable witness, a

defendant must make “some plausible showing of how [his] testimony would have

been both material and favorable to his defense.” United States v.

Valenzuela-Bernal, 458 U.S. 858, 873 (1982); United States v. Caballero, 277

F.3d 1235, 1241 (10th Cir. 2002). In addition to materiality, we have held that a

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defendant must also “demonstrate governmental bad faith to obtain an order

dism issing [his] indictment.” C aballero, 277 F.3d at 1242. Here, however, we

need not decide whether M r. Sierra-Estrada met his burden to show bad faith on

the part of the government because the testimony of M r. Sanchez was not

material. Id. (“[F]ailure to show the materiality of . . . lost testimony absolves us

of examining the bad faith prong.”). Evidence is material “only if there is a

reasonable likelihood that the testimony could have affected the judgment of the

trier of fact.” Valenzuela-Bernal, 458 U.S. at 874. There is no such likelihood

here.

First and foremost, the evidence that M r. Sierra-Estrada conspired to

distribute methamphetamine can only be described as overwhelming. This

evidence included M r. Sierra-Estrada’s confession to the FBI that he created the

hidden compartment in the cooler in which the methamphetamine was found for

$500, that he placed the methamphetamine in the cooler, and that he

directed M r. Sanchez to “take the methamphetamine and not to be afraid.” Supp.

Rec. vol. VI, at 58. The government also introduced evidence that M r. Sanchez’s

car had been seen leaving M r. Sierra-Estrada’s apartment, that M r. Sierra-Estrada

had been observed carrying a cooler similar to the one in which the

methamphetamine was discovered into his apartment, that M r. Sierra-Estrada

discussed M r. Sanchez’s arrest during an intercepted phone call, and that a napkin

discovered in M r. Sanchez’s car contained M r. Sierra-Estrada’s phone number.

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Furthermore, we note that the FBI 302s detailing M r. Sanchez’s statements to the

FBI were introduced at trial. Because the jury convicted M r. Sierra-Estrada

notwithstanding the presence of those statements, we think it is highly unlikely

the jury would have rendered a different verdict had it heard M r. Sanchez testify.

Accordingly, the district court did not abuse its discretion in denying M r. Sierra-

Estrada’s motion to dismiss his indictment.

C. P ROSECUTORIAL M ISCONDUCT

M r. Sierra-Estrada also contends the district court erred in denying his

motion for a mistrial based on the rebuttal portion of the prosecutor’s closing

argument. There, the prosecutor stated:

Tomorrow , our nation lays to rest President Reagan. Those of you who were
alive during the presidency w ill remember he often talked about America
being a shining city on the hill. W e stand for something. W e stand for the
right to have a jury trial when you’re accused by the U nited States of America
of a crime. That doesn’t mean that the jury trial has to find beyond any doubt
that you’re guilty. It’s beyond a reasonable doubt. Your duty, as you retire
to deliberate, is to be part of that city on the hill. Tell Sierra-Estrada that
coming to our country to deal methamphetamine, to deal heartache, to deal
heartbreak, to deal destruction is w rong and we will not stand for it.

Id. vol VII, at 27-28 (emphasis added).

M r. Sierra-Estrada asserts that the prosecutor’s reference to President

Reagan’s “city on the hill” “suggested to the jury that it had a civic duty to

convict.” Aplt’s Br. at 18. He also contends the prosecutor’s reference to “our

country” emphasized that M r. Sierra-Estrada “came from a foreign country, spoke

a foreign language, and was not an American citizen,” and thereby “invite[d] the

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jury to . . . convict on the basis of [his] ethnicity.” Id. at 20 (emphasis added).

Because the prosecutor’s statements arguably involved ethnic innuendo,

M r. Sierra-Estrada suggests that we cannot apply harmless error review and that

his conviction should be reversed without examining the prejudicial effect of

those statements, if any. See M cCleskey v. Kemp, 481 U.S. 279, 309 & n.30

(1987) (stating that “[b]ecause of the risk that the factor of race may enter the

criminal justice process, we have engaged in ‘unceasing efforts’ to eradicate

racial prejudice from our criminal justice system” and that “prosecutorial

discretion cannot be exercised on the basis of race”); United States v. Saccocia,

58 F.3d 754, 774 (1st Cir. 1995) (“Due to the singular importance of keeping our

criminal justice system on an even keel, respecting the rights of all persons,

courts must not tolerate prosecutors’ efforts gratuitously to inject issues like race

and ethnicity into criminal trials.”).

W e disagree with M r. Sierra-Estrada’s contention that harmless error

review is unwarranted. Only in “rare cases” will an error be deemed “structural”

and “thus require[] automatic reversal.” W ashington v. Recuenco, 126 S. Ct.

2546, 2551 (2006). “If the defendant had counsel and was tried by an impartial

adjudicator, there is a strong presumption that any other constitutional errors that

may have occurred are subject to harmless-error analysis.” Neder v. United

States, 527 U.S. 1, 8 (1999) (alteration and internal quotation marks omitted).

Because M r. Sierra-Estrada objected contemporaneously and later moved

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for a mistrial based on the prosecutor’s statements, we review the district court’s

decision for abuse of discretion. United States v. Gabaldon, 91 F.3d 91, 94 n.2

(10th Cir. 1996).

Thus, in examining a prosecutor’s allegedly improper statements, we

generally apply a two-part test. United States v. Harlow, 444 F.3d 1255, 1265

(10th Cir. 2006). W e first determine whether the statements were indeed

improper. U nited States v. M artinez-N ava, 838 F.2d 411, 416 (10th Cir. 1988).

W e then assess whether the statements warrant reversal, examining “the curative

acts of the district court, the extent of the misconduct, and the role of the

misconduct within the case as a whole.” United States v. Pulido-Jacobo, 377 F.3d

1124, 1134 (10th Cir. 2004); see also Soap v. Carter, 632 F.2d 872, 878 (10th Cir.

1980) (Seymour, J., dissenting) (considering the significance of the statement in

the context of the trial as a whole, the presence of curative instructions, the

prosecutor’s motive, and the presence of overw helming evidence of guilt). In

considering these factors, we must be mindful that “[t]he Supreme Court has

articulated different harmless-error standards, depending upon whether the error

is of constitutional dimension.” Harlow, 444 F.3d at 1265 (internal quotation

marks omitted).

Non-constitutional errors are harmless unless they have “a ‘substantial

influence’ on the outcome or leave[] one in ‘grave doubt’ as to whether [they] had

such effect.” United States v. Rivera, 900 F.2d 1462, 1469 (10th Cir. 1990) (en

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banc) (quoting Kotteakos v. United States, 328 U.S. 750, 765 (1946)). In

contrast, most constitutional errors may be deemed harmless only if the reviewing

court is convinced beyond a reasonable doubt that the errors did not affect the

outcome of the trial. Harlow, 444 F.3d at 1265. W ith regard to prosecutorial

misconduct, the harmless error standard that we must apply depends upon the

kind of misconduct involved. Compare id. (treating vouching as a non-

constitutional error and examining “whether it had a substantial influence on the

outcome, or leaves us in grave doubt as to whether it had such an effect”) with

United States v. Rahseparian, 231 F.3d 1267, 1275 (10th Cir. 2000) (applying the

beyond a reasonable doubt standard when the prosecutor commented on the

defendant’s failure to testify).

In this appeal, the government does not defend the prosecutor’s statements

on appeal. Instead, it contends that “it is clear beyond a reasonable doubt that the

jury would have returned a guilty verdict absent the allegedly improper

statement.” Aple’s Br. at 26. See also United States v. Kornegay, 885 F.2d 713,

719 (10th Cir. 1989) (“There is no need to examine in depth the existence of error

where the record convincingly shows that the asserted error, whether or not

actually error, was harmless beyond a reasonable doubt.”); cf. United States v.

Doe, 903 F.2d 16, 27-28 (D.C. Cir 1990) (applying the beyond a reasonable doubt

standard to prosecutor’s reference to race in closing argument).

Considering the trial as a whole, we agree with the government that

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the prosecutor’s statements – proper or not – were harmless beyond a

reasonable doubt. First, the district court ameliorated the effect of the

prosecutor’s statements by instructing the jury that the “statements,

objections and arguments of counsel are not evidence.” Supp. Rec. vol.

VII, at 33. See United States v. Broomfield, 201 F.3d 1270, 1277 (10th

Cir. 2000) (concluding that prosecutor’s statement did not influence the

jury and noting that “[t]he court also instructed the jurors that the

statements and arguments of counsel are not to be considered evidence in

the case”). Second, the evidence of M r. Sierra-Estrada’s guilt, especially

his confession to the FBI that he created the hidden compartment in the

cooler, sold the cooler to M r. Sanchez for $500, placed the

methamphetamine inside the cooler, and directed M r. Sanchez to transport

the methamphetamine to Kansas City, was overw helming.

Under these circumstances, the prosecutor’s statements, thought ill-

advised because of the potential ethnic innuendo, were not “flagrant enough

to influence the jury to convict on grounds other than the evidence

presented.” U nited States v. M eienberg, 263 F.3d 1177, 1180 (10th Cir.

2001) (internal quotation marks omitted). This being the case, we conclude

that any misconduct was harmless beyond a reasonable doubt.

D. G OVERNMENT ’ S C ROSS -A PPEAL

In its cross-appeal, the government challenges the district court’s

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decision not to apply a twenty-year mandatory minimum sentence under 21

U.S.C. § 841(b)(1)(A ). That statute provides in part that, if a person is

convicted of distributing methamphetamine in violation of § 841(a)(1),

“after a prior conviction for a felony drug offense has become final, such

person shall be sentenced to a term of imprisonment which may not be less

than 20 years.” 21 U.S.C. § 841(b)(1)(A ). A “felony drug offense” is

defined as “an offense that is punishable by imprisonment for more than

one year under any law of the United States . . . that prohibits or restricts

conduct relating to narcotic drugs, marihuana, anabolic steroids, or

depressant or stimulant substances.” Id. § 802(44).

In the event a defendant challenges the existence of a prior

conviction, the government must prove the alleged felony beyond a

reasonable doubt. Id. § 851(c)(1) (“If the person denies any allegation of

the information of prior conviction, or claims that any conviction alleged is

invalid, . . . . the United States attorney shall have the burden of proof

beyond a reasonable doubt on any issue of fact.”). “[F]or purposes of

determining a felony conviction, what matters is not the actual sentence

which the defendant received, but the maximum possible sentence.” United

States v. William s, 442 F.3d 1259, 1261 (10th Cir. 2006) (alteration and

internal quotation marks omitted).

Here, the government contends that it met this burden by proving

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beyond a reasonable doubt that M r. Sierra-Estrada was convicted in a

California state court of possessing heroin in violation of California H ealth

& Safety Code § 11352. Nevertheless, the government asserts, the district

court erroneously relied on the sentence that he actually received, a 49-day

jail term, in characterizing the conviction as a misdemeanor that could not

be used to enhance his sentence. 2

In response, M r. Sierra-Estrada does not dispute that a conviction

under California H ealth & Safety Code § 11352 for possession of heroin

would constitute a “prior conviction for a felony offense” under 21 U.S.C.

841(b)(1)(A). However, he maintains, the record does not establish beyond

a reasonable doubt that he was convicted of that offense. He further

contends that the district court based its refusal to apply the enhanced

2
W e note the government’s opening brief in its cross-appeal is rife with
error. First, as noted by M r. Sierra-Estrada, the government states that “[i]t is
undisputed that the court records establish that Sierra-Estrada was convicted of
violating Cal. Health & Safety Code § 11351” A ple’s Br. at 44 (emphasis added);
however, “[t]he issue at the evidentiary hearing was whether M r. Sierra-Estrada
had been convicted under § 11352, not § 11351.” A plt’s Reply Br. at 29. In its
reply brief, the government “apologizes for this obvious factual error,” but
maintains that “this error has no impact on the legal analysis” because § 11352,
like § 11351, qualifies as a “prior conviction for a felony drug offense” under 21
U.S.C. § 841(b)(1)(A). G ov’t Reply Br. at 3-4.
Second, as pointed out by M r. Sierra-Estrada, the document attached to the
government’s brief containing the caption “Consolidated Superior and M unicipal
Courts of R iverside County” w as not introduced or discussed in the evidentiary
hearing. Aplt’s Reply Br. at 22 n.10. Thus, this document is not properly before
the court.

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twenty-year minimum on the government’s failure of proof. As a result, he

concludes, the district court’s erroneous reference to the length of his

actual sentence in characterizing the offense as a misdemeanor does not

entitle the government to relief.

1. Standard of Review

W e review de novo the question of whether a rational trier of fact

could find the evidence of a prior conviction sufficient to enhance a

defendant’s sentence under § 841(b)(1)(A). See United States v. Green,

175 F.3d 822, 834 (10th Cir. 1999). W e view the evidence and all

reasonable inferences therefrom in the light most favorable to the verdict.

See id.

2. Sufficiency of the Evidence

At sentencing, the government presented (1) the original felony

complaint alleging that M r. Sierra-Estrada violated Cal. Health & Safety

Code §§ 11351 and 11352; (2) the information charging him with a

violation of § 11352; (3) the docket report showing that he pleaded guilty

to § 11352; (4) the disposition record showing that he pleaded guilty to §

11352; and (5) a California booking photograph of M r. Sierra-Estrada.

Upon considering this evidence, the district court first noted that “the

matter of the enhancement from ten years to 20 years turns upon whether or

not the prior offense was sentenced as a felony or as a misdemeanor.” Rec.

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vol. III, at 10 (emphasis added). The court continued:

I have looked at all of the documents, and I have a copy of the
original felony complaint, the original felony information[,] and
a copy of the docket sheet. But the final document, which seems
to me makes the whole thing ambiguous and troubles me, is the
document that is a form that is used in lieu of what we do in
federal practice, issue a separate judgment and commitm ent, so
that there will be no question about what the offense was and
what the sentence was.

I have two documents. One is the original and one is the
amended form[,] and they are Exhibits A and B. The w ord
felony is crossed out in both of those forms, so it is not quite
correct to say that there is not any basis for questioning it.

And then the sentence goes on to sound very much like a
m isdemeanor sentence. It is a sentence of 49 days in jail and
then probation, probation after a fine of $50 and another amount
in the amount of $85. I can’t tell for sure what happened. It was
presented at the hearing that this was a plea bargain and ended up
being a felony conviction. It sure looks that way. There is
nothing to the contrary, other than the fact that the document, the
operative document that I am looking at, provides for 49 days of
time, $135, including the $50 fine, and various indications about
reporting to a probation officer.

I regard the matter as ambiguous. I regard the prior history in
R iverside , C alifo rnia a s ev idencing sentencing fo r a
m isdemeanor. That is what it appears to me based upon the
document and the testimony at trial.

Id. vol. III, at 10-12 (emphasis added).

W e agree with M r. Sierra-Estrada and the district court that a

factfinder could conclude that the evidence w as insufficient to establish

beyond a reasonable doubt that he was convicted of the felony of

possession of heroin in violation of California Health & Safety Code §

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11352. W e acknowledge that the government’s submission of the docket

report and disposition record indicating that he pleaded guilty to a § 11352

offense w ould ordinarily be convincing evidence of a conviction. However,

as M r. Sierra Estrada observes, the government failed to introduce evidence

of a final judgment. The absence of such a judgment is significant because

California law provides that “[a] copy of the judgment of conviction shall

be filed with the papers in the case.” See Cal. Penal Code § 1207

(emphasis added).

M oreover, in the absence of a final judgment, the fact that the w ord

“felony” was crossed out in the probation reports— a matter that the

government failed to explain — supports the inference that M r. Sierra-

Estrada “entered into plea negotiations w ith the prosecutor and ultimately

pled [sic] to a misdemeanor.” Aplt’s Reply Br. at 35 n.16. See Green, 175

F.3d at 833-36 (reversing district court because government failed to prove

beyond a reasonable doubt that defendant had committed two prior felony

convictions because the felonies were in names used by the defendant as

aliases and the government did not produce any physical evidence – like a

picture or fingerprints – linking the defendant to the prior convictions); see

also United States v. Stallings, 301 F.3d 919, 921 (8th Cir. 2002) (holding

that the district court’s reliance on a prior California conviction to enhance

a defendant’s sentence was improper after it concluded that “judgment was

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never properly entered against [the defendant]”).

A transcript of the plea hearing would have been helpful. “[T]he

court’s oral pronouncement of judgment . . . . controls over the clerk’s

minute order . . . .” People v. Farell, 28 Cal. 4th 381, 384 n.2 (2002); see

also People v. M esa, 14 Cal. 3d 466, 471 (1975) (“[A] discrepancy between

the judgment as orally pronounced and as entered in the minutes is

presumably the result of clerical error.”). However, the government

conceded at sentencing that it did not attempt to procure a plea hearing

transcript.

W e agree with M r. Sierra-Estrada that the district court based its

refusal to impose the 20-year enhanced sentence under § 841(b)(1)(A ) in

part on the government’s failure to prove beyond a reasonable doubt that he

was actually convicted of a felony under California Health & Safety Code §

11352. See Rec. vol. III, at 11-12 (“I regard the matter as ambiguous. I

regard the prior history in Riverside, California as evidencing sentencing

for a misdemeanor. That is what it appears to me based upon the document

and the testimony at trial.”). Accordingly, the district court’s erroneous

statement that “the matter of the enhancement from ten years to 20 years

turns upon whether or not the prior offense was sentenced as a felony or as

a misdemeanor,” Rec. vol. III, at 10 (emphasis added), does not entitle the

government to relief. Even if the district court had not so erred, the

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ambiguities it noted establish a reasonable doubt regarding the alleged

felony conviction.

III. CONCLUSION

Therefore, we AFFIRM the district court’s denial of M r. Sierra-

Estrada’s motions to suppress inculpatory statements, dismiss the

indictment, and grant a mistrial. W e also A FFIRM the district court’s

imposition of a ten-year sentence.

Entered for the Court,

Robert H. Henry

Circuit Judge

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