     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
                     ____________
                             Submitted: April 12, 2016
                                Filed: July 22, 2016
                                  ____________

Before GRUENDER and KELLY, Circuit Judges, and ERICKSEN,1 District
Judge.
                         ____________

GRUENDER, Circuit Judge.

      Alejandro Valencia and Eric Octavio Rangel-Ortega pleaded guilty to several
drug-related offenses. The district court2 sentenced Valencia to 292 months’
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 of methamphetamine from Rangel-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


      1
      The Honorable Joan N. Ericksen, United States District Judge for the District
of Minnesota, sitting by designation.
      2
        The Honorable Dean Whipple, United States District Judge for the Western
District of Missouri.

                                         -2-
officer contacted Rangel-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.




                                         -3-
       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 this summary, 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



                                         -4-
advisory sentencing guidelines range 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

                                          -5-
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 bears the 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 of the statutory maximum, 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 falls far below the
statutory-maximum sentence of life imprisonment available for his convictions. “We
have repeatedly held that, in the face of a valid appeal waiver, any sentence within the

                                          -6-
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 questioned Rangel-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.”). Rangel-
Ortega 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 was satisfied 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

                                          -7-
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.3 See United
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.




      3
        Several of our sister circuits have held that “[w]hen a district court has advised
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).

                                           -8-
       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 or the extensiveness of the 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 couriers to meet him at a specific location, and he explained that he would

                                           -9-
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.




                                        -10-
                                     III.


     For the foregoing reasons, we affirm Valencia’s sentence, and we dismiss
Rangel-Ortega’s appeal.
                     ______________________________




                                    -11-
