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Date: 10-10-2021
Case Style:
United States of America v. ROBERTO SIERRA-ESTRADA, a/k/a Chorizo
Case Number: 05-4086 05-4117
Judge: Robert H. Henry
Court: UNITED STATES COURT OF APPEALS
TENTH CIRCUIT
Plaintiff's Attorney: United States Attorney’s Office
Defendant's Attorney:
Description:
Denver, CO - Criminal defense lawyer represented defendant with a conspiring to distribute methamphetamine charge.
On March 7, 2001, the FBI received a tip from a confidential informant that
Mr. 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 Mr. 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 Mr. Sierra-Estrada carry a
red and white cooler into the apartment. When Mr. Sanchez left the apartment by
himself in the Lincoln, the FBI notified the Utah Highway Patrol.
Utah Highway Patrol Troopers stopped Mr. 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 Mr. 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 Mr. Sanchez.
Approximately a week-and-a-half after Mr. Sanchez’s arrest, the FBI
intercepted a telephone call between Mr. Sierra-Estrada and Leonel AcevedoTorres, 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, Mr. Sierra-Estrada told Mr. Acevedo-Torres, in code,
about Mr. Sanchez’s arrest and the large amount of methamphetamine that had
been confiscated by law enforcement. Mr. Sierra-Estrada further stated that, due
in part to Mr. Sanchez’s arrest, he would be unable to pay for drugs previously
advanced by Mr. Acevedo-Torres.
On April 18, 2001, Mr. Sanchez was indicted for possession of
methamphetamine with intent to distribute. The FBI subsequently conducted two
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 Mr. Sanchez’s vehicle bearing Mr. Sierra-Estrada’s cell
phone number.
During the initial interview, Mr. 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 Mr. Sierra-Estrada. He instead stated that he had traveled to
the apartment complex where Mr. Sierra-Estrada lived to meet a man named
“Pedro,” who was not involved with his transportation of the methamphetamine.
When the interviewing agents showed him a picture of Mr. Sierra-Estrada, Mr.
Sanchez indicated that he had met him at a dance in Mexico but did not know his
name or current whereabouts.
During the second interview, Mr. Sanchez again did not mention Mr.
Sierra-Estrada. He provided that he had stopped at the apartment where Mr.
Sierra-Estrada resided to better conceal the methamphetamine in a cooler he had
purchased. According to Mr. Sanchez, he did not know the individuals at the
apartment, and they were unaware he was carrying methamphetamine.
On November 8, 2001, Mr. 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 Mr. 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 Mr. 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 March 1, 2002, at approximately 7:30 p.m., two FBI agents met with
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Mr. 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 Mr. Sierra-Estrada of his rights under Miranda v. Arizona, 384
U.S. 436 (1966), and asked if he wanted to speak with them. In response, Mr.
Sierra-Estrada asked, “I wonder if I could have access to a lawyer. 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. We
would not interview him at that time. We would wait until a later time to do the
interview.” Id.
At approximately 7:42 p.m., the agents presented Mr. Sierra-Estrada with a
Spanish-language “advice of rights” form explaining his Miranda rights. The
form also advised Mr. Sierra-Estrada that he would waive his rights by signing it.
After reading the form to himself, Mr. 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. Mr. 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 Mr. Sierra-Estrada’s concerns regarding the FBI’s ability to
ensure his safety if he cooperated.
Mr. Sierra-Estrada continued to ask the agents questions for around 35 to
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40 minutes. During this time, Mr. 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, Mr. SierraEstrada 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., Mr. Sierra-Estrada
told the agents he wanted to talk to them and signed the advice of rights form.
After doing so, Mr. Sierra-Estrada proceeded to confess to conspiring to
distribute the methamphetamine found in Mr. 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 Mr. Sanchez, that
he placed the methamphetamine in the cooler, that he handed the cooler to Mr.
Sanchez, and that he told Mr. Sanchez, who was nervous, to “take the
methamphetamine and not to be afraid.” Id. vol. VI, at 58. Mr. Sierra-Estrada
also admitted that he was the person speaking to Mr. Acevedo-Torres on the
intercepted phone call and explained the contents of the conversation to the
agents.
On March 4, Mr. Sierra-Estrada spoke with the FBI agents for a second
time. Once again, Mr. Sierra-Estrada was apprised of his Miranda rights through
an interpreter and he signed a Spanish-language advice of rights form. During
this interview, Mr. Sierra-Estrada confirmed his involvement in the transportation
and distribution of illegal narcotics for many years.
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B. PROCEDURAL HISTORY
On March 2, 2002, Mr. Sierra-Estrada was indicted for conspiracy to
distribute the methamphetamine hidden insider the cooler in Mr. Sanchez’s
vehicle.
Prior to trial, he filed a motion to suppress the inculpatory statements he
made during his FBI interviews. 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 Mr. 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 might be
provided in the future. I am satisfied that the answers . . . given by
Agent Ross were appropriate, they were 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 lawyer. He 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. He 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, Mr. Sierra-Estrada’s trial counsel moved the district
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court for authorization to travel to the prison where Mr. 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 Mr. Sanchez from prison and turned him over to
immigration officials for deportation. A memorandum from the Bureau of Prisons
to the FBI indicated that Mr. 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 Mr. 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 Mr. Sanchez.
Inexplicably, these reports were not contained in the government’s previous
discovery disclosures. The district court granted Mr. Sierra-Estrada’s motion.
An investigator for Mr. Sierra-Estrada eventually contacted Mr. Sanchez in
Mexico via telephone. Mr. Sanchez, however, was unwilling to speak about the
case. The FBI then contacted Mr. Sanchez, but he indicated that he was unwilling
to testify for Mr. Sierra-Estrada. He also refused to allow the government or trial
counsel to interview him in Mexico.
Mr. Sierra-Estrada moved to dismiss the indictment because Mr. 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, Mr. SierraEstrada 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 follows:
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 way the deportation.
What 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-examination.
But the most significant thing that could be raised is what was said by
Mr. 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)
Mr. Sierra-Estrada’s custodial statements, (2) the intercepted phone call between
Mr. Sierra-Estrada and Mr. Acevedo-Torres, (3) the note from Mr. Sanchez’s
vehicle containing Mr. Sierra-Estrada’s cell phone number, (4) the seizure of
methamphetamine from the cooler in Mr. Sanchez’s vehicle, and (5) testimony
that Mr. 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 Mr. Sanchez’s statements. During the rebuttal
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We set forth the prosecutor’s statement in more detail below. 1
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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 Mr. 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. Following closing arguments, the court instructed the jury that “[s]tatements,
objections and arguments of counsel are not evidence.” Id. at 33.
After the case was submitted to the jury, Mr. 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 Mr. Sierra-Estrada of
conspiracy to distribute methamphetamine in violation of 21 U.S.C. §§ 841(a)(1)
and 846.
C. SENTENCING
Following Mr. Sierra-Estrada’s conviction, the United States Probation
Office prepared a presentence investigation report (“PSR”). The PSR noted that
Mr. 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
Mr. Sierra-Estrada had an offense level of 34 and a criminal history category of I,
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his recommended Sentencing Guidelines range was 151 to 188 months. However,
because the government had filed an information prior to trial pursuant to 21
U.S.C. § 851 alleging that Mr. Sierra-Estrada was 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).
Mr. 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 Mr.
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 Mr. Sierra-Estrada with violating Cal. Health
& Safety Code §§ 11351 (Counts I & III) and 11352 (Counts II and IV); (2) a
criminal information, charging Mr. Sierra-Estrada with two counts of violating §
11352; (3) a copy of the docket, showing that Mr. Sierra-Estrada pleaded guilty to
§ 11352 and was granted 36 months probation; and (4) a disposition sheet
purporting to show a history of Mr. Sierra-Estrada’s case from arrest through
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sentencing. These documents indicated that the offense of conviction was a
felony.
Although Mr. Sierra-Estrada conceded that possession of heroin was a
felony, he argued the government failed to prove that conviction beyond a
reasonable doubt. For support, Mr. Sierra-Estrada introduced two probation
reports, both with the word “felony” crossed out and granting probation to Mr.
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 word
“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 Mr. Sierra-Estrada to the mandatory
minimum ten years’ imprisonment. Id. at 12.
Both parties filed timely notices of appeal.
II. DISCUSSION
On appeal, Mr. Sierra-Estrada challenges the district court’s denial of (1)
his motion to suppress the inculpatory statements he made during his FBI
interviews, (2) his motion to dismiss the indictment, and (3) his motion for a
mistrial. We address these challenges in turn.
A. INVOCATION OF RIGHT TO COUNSEL
Mr. 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. McKerrell, 491 F.3d 1221,
1224-25 (10th Cir. 2007). Accordingly, in assessing whether the district court
properly determined that Mr. Sierra-Estrada failed to invoke the right to counsel,
we accept the district court’s factual findings regarding the words Mr. SierraEstrada used unless they are clearly erroneous. United States v. March, 999 F.2d
456, 459 (10th Cir. 1993). We review de novo, however, “[w]hether those words
actually invoked the right to counsel.” Id. (internal quotations and citation
omitted).
Under Miranda, law enforcement officers must 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 Davis 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, “Maybe 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 lawyer”
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 answering “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 “What time will I see a lawyer?” was not a clear invocation).
Applying the Supreme Court’s decision in Davis to his case, Mr. SierraEstrada first contends he unambiguously invoked his right to counsel at the outset
of his first FBI interview when he inquired, “I wonder if I could have a lawyer.
Is it possible if I don’t have money?” Supp. Rec. vol. II, at 14. We 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 Mr. 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 lawyer 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 Mr. 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, Mr. Sierra-Estrada contends that a reasonable officer would
have understood him to have requested counsel prior to waiving his
Miranda rights because he referenced an attorney multiple times over the fortyseven minutes preceding his waiver, he had no understanding of American laws,
and he could not speak English. But an examination of the circumstances
surrounding Mr. Sierra-Estrada’s waiver indicates just the opposite. First, Mr.
Sierra-Estrada’s additional inquires as to whether “he could get a lawyer in the
future if he wanted 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-Galindo, 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 Mr. SierraEstrada’s request for counsel was lost in translation; an FBI interpreter was
present throughout the interview and Mr. Sierra-Estrada agreed both orally and in
writing to waive his Miranda 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 Mr. Sierra-Estrada’s waiver
of his Miranda rights, “reflects . . . careful handling of the matter” by the FBI.
Supp. Rec. vol. III, at 13. Accordingly, Mr. Sierra-Estrada did not invoke his
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right to counsel.
B. DEPORTATION OF GABINO SANCHEZ
Mr. 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 Mr. Sanchez from the United States. At trial, the defense
theory was essentially that Mr. Sierra-Estrada had no knowledge of the
methamphetamine discovered in Mr. Sanchez’s car. Mr. Sierra-Estrada contends
Mr. Sanchez would have corroborated this claim because Mr. Sanchez did not
implicate Mr. 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.” United 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
dismissing [his] indictment.” Caballero, 277 F.3d at 1242. Here, however, we
need not decide whether Mr. Sierra-Estrada met his burden to show bad faith on
the part of the government because the testimony of Mr. 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 Mr. Sierra-Estrada conspired to
distribute methamphetamine can only be described as overwhelming. This
evidence included Mr. 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 Mr. Sanchez to “take the methamphetamine and not to be afraid.” Supp.
Rec. vol. VI, at 58. The government also introduced evidence that Mr. Sanchez’s
car had been seen leaving Mr. Sierra-Estrada’s apartment, that Mr. Sierra-Estrada
had been observed carrying a cooler similar to the one in which the
methamphetamine was discovered into his apartment, that Mr. Sierra-Estrada
discussed Mr. Sanchez’s arrest during an intercepted phone call, and that a napkin
discovered in Mr. Sanchez’s car contained Mr. Sierra-Estrada’s phone number.
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Furthermore, we note that the FBI 302s detailing Mr. Sanchez’s statements to the
FBI were introduced at trial. Because the jury convicted Mr. 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 Mr. Sanchez testify.
Accordingly, the district court did not abuse its discretion in denying Mr. SierraEstrada’s motion to dismiss his indictment.
C. PROSECUTORIAL MISCONDUCT
Mr. 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 will remember he often talked about America
being a shining city on the hill. We stand for something. We stand for the
right to have a jury trial when you’re accused by the United 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 wrong and we will not stand for it.
Id. vol VII, at 27-28 (emphasis added).
Mr. 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 Mr. 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,
Mr. 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 McCleskey 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.”).
We disagree with Mr. 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.” Washington 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 Mr. 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). We first determine whether the statements were indeed
improper. United States v. Martinez-Nava, 838 F.2d 411, 416 (10th Cir. 1988).
We 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 overwhelming 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. With 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 nonconstitutional 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 Mr. Sierra-Estrada’s guilt, especially
his confession to the FBI that he created the hidden compartment in the
cooler, sold the cooler to Mr. Sanchez for $500, placed the
methamphetamine inside the cooler, and directed Mr. Sanchez to transport
the methamphetamine to Kansas City, was overwhelming.
Under these circumstances, the prosecutor’s statements, thought illadvised because of the potential ethnic innuendo, were not “flagrant enough
to influence the jury to convict on grounds other than the evidence
presented.” United States v. Meienberg, 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. GOVERNMENT’S CROSS-APPEAL
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. Williams, 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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We note the government’s opening brief in its cross-appeal is rife with 2
error. First, as noted by Mr. 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” Aple’s Br. at 44 (emphasis added);
however, “[t]he issue at the evidentiary hearing was whether Mr. Sierra-Estrada
had been convicted under § 11352, not § 11351.” Aplt’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). Gov’t Reply Br. at 3-4.
Second, as pointed out by Mr. Sierra-Estrada, the document attached to the
government’s brief containing the caption “Consolidated Superior and Municipal
Courts of Riverside County” was 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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beyond a reasonable doubt that Mr. Sierra-Estrada was convicted in a
California state court of possessing heroin in violation of California Health
& 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, Mr. Sierra-Estrada does not dispute that a conviction
under California Health & 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
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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
We 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). We 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 Mr. 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 Mr. 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 commitment, 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 word
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
misdemeanor 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
Riverside, California as evidencing sentencing for a
misdemeanor. That is what it appears to me based upon the
document and the testimony at trial.
Id. vol. III, at 10-12 (emphasis added).
We agree with Mr. Sierra-Estrada and the district court that a
factfinder could conclude that the evidence was 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. We acknowledge that the government’s submission of the docket
report and disposition record indicating that he pleaded guilty to a § 11352
offense would ordinarily be convincing evidence of a conviction. However,
as Mr. 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).
Moreover, in the absence of a final judgment, the fact that the word
“felony” was crossed out in the probation reports—a matter that the
government failed to explain —supports the inference that Mr. SierraEstrada “entered into plea negotiations with 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. Mesa, 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.
We agree with Mr. 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.
Outcome: Therefore, we AFFIRM the district court’s denial of Mr. SierraEstrada’s motions to suppress inculpatory statements, dismiss the
indictment, and grant a mistrial. We also AFFIRM the district court’s
imposition of a ten-year sentence.
Plaintiff's Experts:
Defendant's Experts:
Comments: