Document ID: s3://data.kl3m.ai/documents/govinfo/USCOURTS/USCOURTS-ca8-15-02173/USCOURTS-ca8-15-02173-0/pdf.json

Parties Involved:
United States of America
Appellee
Alejandro Valencia
Appellant

Document Text:

United States Court of Appeals

For the Eighth Circuit

___________________________

No. 15-2173

___________________________

United States of America

lllllllllllllllllllll Plaintiff - Appellee

v.

Alejandro Valencia, also known as Pablo Villanueva-Acosta

lllllllllllllllllllll Defendant - Appellant

___________________________

No. 15-2192

___________________________

United States of America

lllllllllllllllllllll Plaintiff - Appellee

v.

Eric Octavio Rangel-Ortega

lllllllllllllllllllll Defendant - Appellant

____________

Appeals from United States District Court 

for the Western District of Missouri - Kansas City

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Appellate Case: 15-2173 Page: 1 Date Filed: 07/22/2016 Entry ID: 4429192 
Submitted: April 12, 2016

 Filed: July 22, 2016

____________

Before GRUENDER and KELLY, Circuit Judges, and ERICKSEN, District 1

Judge.

____________

GRUENDER, Circuit Judge.

Alejandro Valencia and Eric Octavio Rangel-Ortega pleaded guilty to several

drug-related offenses. The district court sentenced Valencia to 292 months’ 2

imprisonment and Rangel-Ortega to 240 months’ imprisonment. Both Valencia and

Rangel-Ortega now appeal, arguing that the district court erred by enhancing their

sentences based on their roles in the offenses. We dismiss Rangel-Ortega’s appeal,

and we affirm Valencia’s sentence.

I.

In 2012, law enforcement began investigating a Mexico-based drug-trafficking

organization operating in Kansas City. The local recipients of the imported cocaine

and methamphetamine were Alejandro Valencia and Eric Octavio Rangel-Ortega. 

From October 2012 to January 2013, undercover investigators conducted several

controlled purchases ofmethamphetamine fromRangel-Ortega. When Rangel-Ortega

returned to Mexico in early 2013, he referred the investigators to his partner Valencia

for future methamphetamine purchases. Prior to each transaction, the undercover

The Honorable Joan N. Ericksen, United States District Judge for the District 1

of Minnesota, sitting by designation.

The Honorable Dean Whipple, United States District Judge for the Western

2

District of Missouri.

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officer contactedRangel-Ortega to ensure Valencia would complete the sale. In total,

the investigators conducted five controlled purchases from Valencia.

Following these events, a grand jury indicted Rangel-Ortega and Valencia. 

Rangel-Ortega pleaded guilty to conspiracy to distribute 500 grams or more of

methamphetamine, in violation of 21 U.S.C. §§ 841(a)(1) and 846; and distribution

of methamphetamine, in violation of 21 U.S.C. § 841(a)(1). Valencia pleaded guilty

to conspiracy to distribute and possess with the intent to distribute five kilograms or

more of cocaine and 500 grams or more of methamphetamine, in violation of 21

U.S.C. §§ 841(a)(1) and 846; conspiracy to import five kilograms or more of cocaine,

in violation of 21 U.S.C. §§ 952(a), 960(a)(1), and 963; and bulk cash smuggling, in

violation of 31 U.S.C. § 5332(a)(1). In addition, both men pleaded guilty to

conspiracy to commit money laundering, in violation of 18 U.S.C. § 1956(a)(1)(A)(I).

The two plea agreements contained the same appellate waiver:

[T]he defendant expressly waives the right to appeal any sentence,

directly or collaterally, on any ground except claims of (1) ineffective

assistance of counsel; (2) prosecutorial misconduct; or (3) an illegal

sentence. An “illegal sentence” includes a sentence imposed in excess

of the statutory maximum, but does not include less serious errors, such

as misapplication of the Sentencing Guidelines, an abuse of discretion,

or the imposition of an unreasonable sentence.

At Rangel-Ortega’s change-of-plea hearing, the district court examined him to

ensure that he understood the components of the plea agreement. The court reminded

Rangel-Ortega that he was waiving his appellate rights on all but three grounds:

ineffective assistance of counsel, prosecutorial misconduct, and imposition of an

illegal sentence. Rangel-Ortega confirmed his understanding of the agreement and

the rights he waived. The district court then accepted Rangel-Ortega’s plea.

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The court referred Valencia’s change-of-plea hearing to a magistrate judge. 

The magistrate judge confirmed that Valencia had read, understood, and consulted

an attorney about the plea agreement. However, the magistrate judge misstated the

scope of Valencia’s appellate waiver by informing him that he only waived the right

to appeal “as long as the sentence is reasonable and not greater than the statutory

maximums.” Valencia confirmed his understanding of thissummary, and the district

court accepted his plea in accordance with the magistrate judge’s recommendation. 

The presentence investigation reports for both Rangel-Ortega and Valencia

recommended an enhancement under USSG § 3B1.1 based on their leadership roles

in the drug-trafficking offenses. Both men objected to this enhancement, arguing that

the evidence did not support its imposition. As a result, the Government called

Special Agent Matt Hall of the Department of Homeland Security to testify at each

sentencing hearing.

At Rangel-Ortega’s sentencing hearing, Special Agent Hall testified that

Rangel-Ortega told undercover officers that he could obtain whatever they desired

through his connections in Mexico. Agent Hall also testified that the freedom with

which Rangel-Ortega crossed the border—despite his illegal status—displayed that

he was well connected and that he had mid-level status within the drug organization.

In addition, Agent Hall stated that Rangel-Ortega’s supervisory authority was

demonstrated by the fact that even after he left the country, he orchestrated an

undercover officer’s contact with Valencia in order to facilitate additional drug

purchases. Finally, Agent Hall testified that Valencia sent money from the local

Kansas City transactions to Rangel-Ortega. Based on this testimony, the court

overruled Rangel-Ortega’s objection and applied the four-level sentencing

enhancement pursuant to USSG § 3B1.1(a) for Rangel-Ortega’s role as an organizer

or leader of a criminal activity that involved five or more participants or that was

otherwise extensive. The court ultimately varied downward from Rangel-Ortega’s

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Appellate Case: 15-2173 Page: 4 Date Filed: 07/22/2016 Entry ID: 4429192 
advisory sentencing guidelinesrange of 262-327 months to impose a sentence of 240

months’ imprisonment.

At Valencia’s sentencing hearing, Agent Hall described Valencia as the

organization’s point of contact in Kansas City. Agent Hall testified that undercover

agents made several purchases from Valencia after Rangel-Ortega went to Mexico.

Agent Hall also explained that law enforcement had intercepted thirty-one hours of

phone conversations between members of the drug-trafficking ring. During one of

these intercepted conversations, Valencia provided directions to two couriers who

were bringing a shipment of drugs from Mexico to Kansas City. As part of this

transaction, Valencia also called the girlfriend of the drug-trafficking organization’s

supplier and told her to bring a scale so he could weigh the cocaine. Finally, after the

transaction, Valencia contacted the organization’s supplier to report that the $330,000

transaction had been successful.

Agent Hall also testified that Valencia called a local drug dealer when a new

drug shipment arrived. Valencia referenced collecting payment from this seller and

alluded to the fact that he had fronted cocaine to the dealer in the past. Based on the

agent’s testimony, the court rejected Valencia’s objection and imposed a three-level

enhancement under § 3B1.1(b) for Valencia’s role as a manager or supervisor in a

criminal activity involving five or more participants or that was otherwise extensive.

The court then imposed a sentence of 292 months’ imprisonment, a sentence at the

bottom of Valencia’s advisory guidelines range of 292-365 months.

II.

On appeal, Rangel-Ortega and Valencia challenge the district court’s decision

to impose the sentencing guidelines enhancements based on their roles in the

offenses. Rangel-Ortega contends that the district court erred when it applied the

four-level enhancement under USSG § 3B1.1(a) because the decision was not based

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Appellate Case: 15-2173 Page: 5 Date Filed: 07/22/2016 Entry ID: 4429192 
on the factors laid out in the Guidelines. Valencia argues that the district court erred

by improperly applying the three-level enhancement under USSG § 3B1.1(b) because

the enhancement was not supported by the evidence. The Government responds that

both appeals should be dismissed because the waivers in Rangel-Ortega’s and

Valencia’s plea agreements bar them from raising these appeals.

When a plea agreement contains an appellate waiver, our court generally will

enforce it “as long as the appeal falls within the scope of the waiver, and the

defendant’s accession to the plea agreement was knowing and voluntary.” United

States v. Azure, 571 F.3d 769, 772 (8th Cir. 2009). The Government bearsthe burden

of “establishing that the plea agreement clearly and unambiguously waives the

defendant’s right to appeal.” Id. “We review de novo the issue of whether a

defendant has knowingly and voluntarily waived rights in a plea agreement.” United

States v. Selvy, 619 F.3d 945, 949 (8th Cir. 2010) (quoting United States v. Swick,

262 F.3d 684, 686 (8th Cir. 2001)). Even when the agreement is unambiguous and

the waiver is knowing, however, we refrain from enforcing the waiver if enforcement

would result in a miscarriage of justice. Azure, 571 F.3d at 772.

We begin with Rangel-Ortega’s appeal. Rangel-Ortega’s plea agreement stated

that he “expressly waive[d] the right to appeal any sentence, directly or collaterally,

on any ground except claims of(1) ineffective assistance of counsel;(2) prosecutorial

misconduct; or (3) an illegal sentence.” The agreement defined an “illegal sentence”

as a sentence imposed in excess ofthe statutorymaximum, but not a sentence affected

by “less serious sentencing errors, such as misapplication of the Sentencing

Guidelines, an abuse of discretion, or the imposition of an unreasonable sentence.”

Although Rangel-Ortega argues that his advisory sentencing guidelines range was

calculated improperly, he does not contend that the sentence was illegal—i.e., that it

exceeded the statutory maximum. Indeed, his 240-month sentence fallsfar below the

statutory-maximumsentence of life imprisonment available for his convictions. “We

have repeatedly held that, in the face of a valid appeal waiver, any sentence within the

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Appellate Case: 15-2173 Page: 6 Date Filed: 07/22/2016 Entry ID: 4429192 
statutory range is not subject to appeal” as an illegal sentence. United States v. Sisco,

576 F.3d 791, 795 (8th Cir. 2009). This holding is consistent with the language of

his waiver defining an “illegal sentence” exclusively as a sentence in excess of the

statutory maximum. Rangel-Ortega’s challenge to the enhancement is a challenge to

the court’s application of the Guidelines, and it thus falls squarely within the scope

of his waiver.

We further conclude that Rangel-Ortega’s waiver was knowing and voluntary.

At the change-of-plea hearing, the district court questionedRangel-Ortega to confirm

that he fully understood the plea agreement and that he had consulted his attorney

about its contents. The court then informed Rangel-Ortega that his plea agreement

contained an appellate waiver and asked Rangel-Ortega if he understood that he

waived the right to appeal the sentence imposed on any ground other than ineffective

assistance of counsel, prosecutorial misconduct, or an illegal sentence. See United

States v. Andis, 333 F.3d 886, 890-91 (8th Cir. 2003) (en banc) (“One important way

a district court can help ensure that a plea agreement and corresponding waiver are

entered into knowingly and voluntarily is to properly question a defendant about his

or her decision to enter that agreement and waive the right to appeal.”). RangelOrtega replied that he understood, and he acknowledged that he would be bound by

the agreement’s terms. He further indicated that he entered into the plea voluntarily

and that he wassatisfied with his counsel’s performance. In light of this colloquy and

Rangel-Ortega’s responses, we see no barrier to enforcing the waiver on this ground.

See United States v. Guzman, 707 F.3d 938, 942 (8th Cir. 2013) (finding a waiver

knowing and voluntary when the defendant confirmed his understanding at his

change-of-plea hearing).

Finally, we conclude that enforcement of the waiver will not result in a

miscarriage of justice. Andis, 333 F.3d at 891. “Although we have not provided an

exhaustive list of the circumstances that might constitute a miscarriage of justice, we

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recognize that these waivers are contractual agreements between a defendant and the

Government and should not be easily voided by the courts.” Id. Here, Rangel-Ortega

raises only a challenge to the district court’s application of the Guidelines to arrive

at a sentence that falls below the statutory maximum. Having reviewed the record,

we find that his claim does not trigger the miscarriage-of-justice exception. See

United States v. Boroughf, 649 F.3d 887, 890 (8th Cir. 2011) (“‘[A]n allegation that

the sentencing judge misapplied the Sentencing Guidelines or abused his or her

discretion’ does not, in the face of a valid appeal waiver, constitute a miscarriage of

justice.” (quoting Andis, 33 F.3d at 892)). We decline Rangel-Ortega’s invitation to

unnecessarily broaden this exception, and we therefore dismiss his appeal.

Although his plea agreement contained the same appeal waiver, Valencia’s

appeal requires a different analysis. At the change-of-plea hearing, the magistrate

judge misstated the waiver’s scope by advising Valencia that he would be unable to

appeal only if “the sentence is reasonable and not greater than the statutory

maximums.” The Government did not object to this statement. Given the magistrate

judge’s misstatement, we elect to resolve the present appeal by assuming without

deciding that Valencia’s waiver does not preclude his present challenge. See United

3

States v. Jones, 756 F.3d 1121, 1122 n.2 (8th Cir. 2014) (per curiam) (assuming that

the waiver did not preclude the appeal and addressing the merits). Accordingly, we

turn to the merits.

Several of our sister circuits have held that “[w]hen a district court has advised

3

a defendant that, contrary to the plea agreement, he is entitled to appeal his sentence,

the defendant can hardly be said to have knowingly waived his right of appeal.”

United States v. Manigan, 592 F.3d 621, 628 (4th Cir. 2010); accord United States

v. Zink, 107 F.3d 716, 718 (9th Cir. 1997); United States v. Ready, 82 F.3d 551, 557-

58 (2d Cir. 1996), superseded on other grounds by United States v. Cook, 722 F.3d

477, 481 (2d Cir. 2013).

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Valencia argues that the district court erred when it applied a sentencing

guidelines enhancement based on his role as a manager or supervisor of a criminal

activity that involved five or more participants or that was otherwise extensive. See

USSG § 3B1.1(b). He raises no argument regarding the court’s finding on the

number of participants orthe extensiveness ofthe criminal activity; instead, he argues

that the court erred by finding that he held a supervisory role. We review the court’s

factual finding of a defendant’s role in the offense for clear error. United States v.

Pena, 67 F.3d 153, 156 (8th Cir. 1995).

Our court has “defined the terms ‘manager’ and ‘supervisor’ quite liberally.”

United States v. Lopez, 431 F.3d 313, 318 (8th Cir. 2005). “[A] defendant can be

subject to this enhancement for having managed or supervised only one other

participant in the criminal conspiracy.” Id. “In addition, the manager or supervisor

enhancement ‘may apply even if the management activity was limited to a single

transaction.’” Id. (quoting United States v. Zimmer, 299 F.3d 710, 724 (8th Cir.

2002)). “The key factors in determining management or supervisory authority are

control over participants and organization of the criminal activity.” Pena, 67 F.3d 

at 156-57. The court must consider the defendant’s exercise of decision-making

authority, the nature of his participation in the offense, and his degree of participation

in planning or organizing the activity. USSG § 3B1.1 cmt. n.4.

We conclude that the court did not clearly err when it found that Valencia acted

as a manager or supervisor for the drug-distribution ring. The evidence showed that

Valencia directed other members of the organization and enlisted their aid during at

least one drug shipment. See United States v. Bahena, 223 F.3d 797, 804 (8th Cir.

2000). Agent Hall testified that he intercepted a phone conversation in which

Valencia gave directions to two couriers who were bringing drugs to Kansas City. 

In the intercepted phone conversation, Valencia dictated the details of the shipment. 

He told the couriersto meet him at a specific location, and he explained that he would

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switch vehicles with the couriers in order to take the drugs to a stash house. Once he

brought the drugs to the stash house, Valencia enlisted the aid of another drug-ring

participant by calling her and telling her to bring a scale to weigh the new shipment

of cocaine. Valencia then drove the empty van back to the couriers and gave them

money. This testimony showed that Valencia personally managed the transaction and

was responsible for ensuring that the deal took place. Such conduct was sufficient

to support the three-level § 3B1.1 enhancement. See United States v. Moreno, 679

F.3d 1003, 1004 (8th Cir. 2012) (per curiam) (affirming a three-level enhancement

when the defendant acted as the conspiracy leader’s “eyes and ears” by ensuring that

“the operation went according to plan and that the proceeds got back to California”);

United States v. Flores, 73 F.3d 826, 836 (8th Cir. 1996) (upholding a § 3B1.1

enhancement after finding that the defendant was entrusted with ensuring “the

$200,000 deal got done”).

In addition, the court heard that Valencia fronted drugs to a local seller. We

previously have recognized that such conduct—while not independently sufficient

to support a § 3B1.1(b) enhancement, see United States v. Del Toro-Aguilera, 138

F.3d 340, 343 (8th Cir. 1998)—is relevant to the court’s analysis of the defendant’s

role in the offense because it demonstrates that the defendant “retained the financial

risk of distribution.” Pena, 67 F.3d at 156. Here, the evidence that Valencia assumed

such risk reinforced the conclusion that Valencia “overstepped a mere seller’s role,”

id., in the criminal activity. Accordingly, we conclude that the court did not clearly

err by finding that Valencia acted as a manager or supervisor. We therefore uphold

the court’s decision to apply the three-level enhancement to his sentence.

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III.

For the foregoing reasons, we affirm Valencia’s sentence, and we dismiss

Rangel-Ortega’s appeal.

______________________________

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