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* This order and judgment is not binding precedent except under the doctrines of law of the case, res judicata and collateral estoppel.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
-2- 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,
-3- 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
-4- 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
-5- 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.
-6- 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
-7- 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
-8- 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
-9- 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.
-10- 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
-11- 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
-12- 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.
-13- 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)
-14- (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
-15- “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
-16- 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
-17- 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.
-18- 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
-19- 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
-20- 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
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
-21- 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
-22- 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
-23- 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
-24- 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.
-25- 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.
-26- 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 §
-27- 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
-28- 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
-29- 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
-30-