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United States of America v. Antonio Moreno-Membache
Case Number: 19-3051
Judge: Patricia Ann Millett
Court: United States Court of Appeals
FOR THE DISTRICT OF COLUMBIA CIRCUIT
Plaintiff's Attorney: James I. Pearce, Attorney, U.S. Department of Justice,
argued the cause and filed the brief for appellee. John M.
Washington, DC - Criminal defense lawyer represented defendant with
a drug-smuggling conspiracy charge.
In June 2012, the United States Coast Guard surveilled the
Mistby, a so-called “go-fast” boat, off the coast of Panama.2
When the Coast Guard approached, the Mistby fled. As the
Coast Guard pursued the boat, the Mistby’s crew began
dumping cargo overboard. To no avail. The Coast Guard soon
interdicted the Mistby and retrieved the discarded cargo, which
amounted to more than 220 kilograms of cocaine and more than
235 kilograms of marijuana.
Moreno-Membache was not a member of the Mistby’s
crew, nor was he present when the ship was stopped. See
2 A “go-fast” boat is “a type of boat that can travel at high rates
of speed and thus is considered a favored vehicle for drug smuggling
operations.” United States v. Tinoco, 304 F.3d 1088, 1117 (11th Cir.
United States v. Mosquera-Murillo, 902 F.3d 285, 287–288
(D.C. Cir. 2018). Instead, he was arrested and extradited to the
United States after a joint investigation of the Colombian and
United States governments concluded that he was involved in
the conspiracy that ultimately resulted in the Mistby’s failed
In January 2016, Moreno-Membache pled guilty to
conspiracy to “knowingly and intentionally distribute, and
possess with intent to distribute * * * on board a vessel subject
to the jurisdiction of the United States” both (i) five kilograms
or more of cocaine, and (ii) 100 kilograms or more of
marijuana. J.A. 130 ¶ 1. The charge was a violation of the
Maritime Drug Law Enforcement Act (“Maritime Drug Act”),
46 U.S.C. §§ 70503, 70506(b), and the Controlled Substances
Import and Export Act, 21 U.S.C. § 960(b)(1)(B), (b)(2)(G).
Under the Maritime Drug Act, the conspiracy charge to
which Moreno-Membache pled carries a mandatory minimum
sentence of ten years in prison. 46 U.S.C. § 70506(a) (stating
that violators of the Maritime Drug Act shall be punished as
provided in 21 U.S.C. § 960(b)); see 21 U.S.C. § 960(b)(1)(B),
(b)(2)(G) (providing for ten-year mandatory minimum).
A separate statutory provision, known as the Safety Valve,
allows district courts to approve sentences below a mandatory
minimum in certain circumstances. Sentencing Reform Act of
1984, Pub. L. No. 98-473, § 212(a), 98 Stat. 1987, 1989–1990
(codified at 18 U.S.C. § 3553(f)). Specifically, the Safety
Valve provision sets out five eligibility criteria for obtaining
relief. 18 U.S.C. § 3553(f). The offense (i) must not have
resulted in death or serious bodily injury to any person, and the
defendant (ii) must not have a significant criminal history,
(iii) must not have used or threatened violence or possessed a
firearm or other dangerous weapon in connection with the
offense, (iv) must not be “an organizer, leader, manager, or
supervisor of others in the offense, as determined under the
sentencing guidelines,” and (v) must truthfully provide all
relevant information and evidence concerning the offense to
the government. 18 U.S.C. § 3553(f)(1)–(5).
Also relevant to this appeal, Moreno-Membache’s plea
agreement was a “C-Plea.” Referencing Federal Rule of
Criminal Procedure 11(c)(1)(C), a “C-Plea” is one that makes
the government’s recommended sentence “binding on the court
‘once the court accepts the plea agreement[.]’” Freeman v.
United States, 564 U.S. 522, 529 (2011) (quoting FED.R.CRIM.
P. 11(c)(1)(C)); accord United States v. Goodall, 236 F.3d 700,
703 (D.C. Cir. 2001). A C-Plea presents the district court with
a take-it-or-leave-it proposition: The court must either accept
or reject the plea; it may not modify the plea’s terms, including
the proposed sentence. See Goodall, 236 F.3d at 703 (citing
United States v. Cunavelis, 969 F.2d 1419, 1422 (2d Cir.
Under the C-Plea, the government and MorenoMembache agreed to a sentence of 120 months (the mandatory
minimum sentence), unless the district court determined that
Moreno-Membache was eligible for relief under the Safety
Valve provision. J.A. 131 ¶ 7. So the district court could either
accept the 120-month sentence or find that Moreno-Membache
deserved a lesser sentence under the Safety Valve provision.
But the district court could not impose a longer sentence.
Under the plea agreement, Moreno-Membache expressly
preserved his ability to seek relief from his mandatory
minimum sentence under the Safety Valve provision. J.A. 132
¶ 9; see also J.A. 132 ¶¶ 6, 7. And the government preserved
its right to argue both that (i) the Safety Valve provision is
categorically inapplicable to Moreno-Membache’s conviction
under the Maritime Drug Act, and (ii) Moreno-Membache does
not meet the Safety Valve eligibility criteria. J.A. 132 ¶ 9.
In the same paragraph of the plea agreement in which the
government preserved its Safety Valve arguments, the
government also surrendered its ability “to seek any of the
adjustments set out in U.S.S.G. Chapter 3, Part B.” J.A. 132
¶ 9. That part of the Sentencing Guidelines includes, as
relevant here, sentencing enhancements for a defendant’s
aggravating role in the offense. U.S. SENTENCING GUIDELINES
MANUAL § 3B1.2 (U.S. SENTENCING COMM’N 2004)
(“U.S.S.G.”). A defendant plays an “aggravating role” when
he acts as an organizer, leader, manager, or supervisor in the
criminal operation. Id.
The district court initially ruled that the Safety Valve
provision had no application to the Maritime Drug Act crimes
to which Moreno-Membache had pleaded guilty. See United
States v. Mosquera-Murillo, 172 F. Supp. 3d 24, 38 (D.D.C.
2016). This court reversed, holding that the Safety Valve was
available for such offenses. Mosquera-Murillo, 902 F.3d
On remand, the district court turned to MorenoMembache’s request for relief under the Safety Valve
provision. United States v. Mosquera-Murillo, No. 13-cr00134-BAH, 2018 WL 6267765, at *1 (D.D.C. Nov. 30, 2018).
Turning to the five statutory criteria for relief, the district court
concluded as to the first and third criteria that MorenoMembache had no serious criminal history and that the crime
did not result in serious injury or death to any person. Id. at *5.
The district court also declined to address the fifth criterion,
which is whether Moreno-Membache fully shared all relevant
information about his criminal activities with the government.
Id. So the district court’s analysis of Moreno-Membache’s
eligibility for relief under the Safety Valve provision turned on
the two remaining criteria: whether Moreno-Membache
performed some leadership or supervisory role in the offense
“as determined under the sentencing guidelines,” and whether
he possessed a weapon in conjunction with the crime, 18
U.S.C. § 3553(f)(2) & (4).
With respect to acting as a leader or supervisor, MorenoMembache contended that the government expressly
surrendered its right to argue that he had served such a role
when it “agree[d] not to seek any of the adjustments set out in
U.S.S.G. Chapter 3, Part B[,]” J.A. 132 ¶ 9, which necessarily
included arguing that he served as an organizer, leader,
manager, or supervisor in the conspiracy, see U.S.S.G. § 3B1.1
cmt. n.2; Joint Status Report at 4–5, 7–8, Mosquera-Murillo,
No. 13-cr-00134-BAH (D.D.C. Nov. 19, 2018), ECF No. 271.
The government disagreed and would present evidence that
Moreno-Membache was ineligible for relief under the Safety
Valve provision because of his alleged supervisory or
managerial role in the offense. Joint Status Report at 6,
Mosquera-Murillo, No. 13-cr-00134-BAH (D.D.C. Nov. 19,
2018), ECF No. 271.
The district court ruled that the plea agreement preserved
the government’s ability to argue that Moreno-Membache was
ineligible for Safety Valve relief because of his supervisory or
managerial role. The district court reasoned that, in the plea
agreement, the government waived only its right to seek an
increase in Moreno-Membache’s guideline sentence because
of his alleged leadership status. The district court also pointed
to other provisions of the plea agreement that allowed the
government to “inform the Court and the Probation Office” of
facts relevant to sentencing, J.A. 132 ¶ 8, and to “dispute
sentencing factors or facts material to sentencing,” J.A. 133
After conducting an evidentiary hearing, the district court
found that Moreno-Membache was a supervisor or manager of
crew members involved in the offense. United States v.
Mosquera-Murillo, No. 13-cr-00134-BAH, 2019 WL
3037533, at *12–15 (D.D.C. July 11, 2019).
With respect to the other Safety Valve criterion pertaining
to the use of a firearm in conjunction with the offense, the
district court credited a law enforcement agent’s description of
two cooperating co-conspirators’ claims that MorenoMembache possessed a firearm. The captain of the Mistby
reportedly said that he saw Moreno-Membache with a firearm
at a planning meeting. Mosquera-Murillo, 2019 WL 3037533,
at *15. And a “streetwise” crewmember reportedly said that he
saw what appeared to him to be the outline of a firearm in
Moreno-Membache’s waistband, but he did not see the firearm
Based on its findings as to Moreno-Membache’s
supervisory or managerial status and possession of a firearm in
conjunction with the crimes, the district court ruled that
Moreno-Membache was ineligible for relief from the Maritime
Drug Act’s mandatory minimum sentence under the Safety
Valve provision. The court then sentenced Moreno-Membache
to the mandatory minimum of 120 months in prison. MorenoMembache filed a timely notice of appeal.
The district court had jurisdiction to hear this case under
18 U.S.C. § 3231, which gives the district courts of the United
States original jurisdiction over “all offenses against the laws
of the United States.” This court has jurisdiction to hear the
appeal of the final judgment in this case under 28 U.S.C.
To determine whether a party has breached the terms of a
plea agreement, we generally apply principles of contract law.
United States v. Henry, 758 F.3d 427, 431 (D.C. Cir. 2014);
United States v. Jones, 58 F.3d 688, 692 (D.C. Cir. 1995). We
interpret the terms of the plea agreement de novo. Henry, 758
F.3d at 431. Consistent with constitutional principles and the
settled rule that contracts are construed against their drafters,
we construe any ambiguities in the plea agreement against the
government. In re Sealed Case, 702 F.3d 59, 65 (D.C. Cir.
At the heart of this case is the ninth paragraph of MorenoMembache’s plea agreement. That paragraph reads, in relevant
The government agrees not to seek any of the
adjustments set out in U.S.S.G. Chapter 3,
Part B. The Defendant is permitted to request
relief under Safety Valve provisions, and the
Government is permitted to argue that the
Safety Valve provisions do not apply to the
maritime offense to which the Defendant has
agreed to plead guilty and that, in any event, the
Defendant does not meet the criteria to qualify
for Safety Valve relief.
J.A. 132 ¶ 9 (emphasis added).
The question is whether the government’s express
agreement not to seek any adjustment under Chapter 3, Part B
of the Sentencing Guidelines—including arguing that MorenoMembache qualified for a supervisory or managerial role
enhancement—foreclosed it from nevertheless arguing that
Moreno-Membache was ineligible for Safety Valve relief
because he was a supervisor or manager “as determined under
the sentencing guidelines,” 18 U.S.C. § 3553(f)(4).
Under settled precedent, ambiguity in the meaning of a
plea agreement must be resolved against the government.
Henry, 758 F.3d at 431; Jones, 58 F.3d at 691. Here, the scope
of the government’s waiver of its right to argue that MorenoMembache had a supervisory or managerial role in the offense
is, at a minimum, ambiguous, and Moreno-Membache
reasonably read the plea agreement as foreclosing the
government’s opposition to his eligibility for Safety Valve
relief on that basis.
To start with, the statutory Safety Valve criterion
regarding supervisory and managerial roles expressly
references the sentencing guidelines. See 18 U.S.C.
§ 3553(f)(4). And Section 5C1.2 of the Sentencing Guidelines,
which specifically implements the Safety Valve criterion in
Section 3553(f)(4), provides that a criminal defendant is
disqualified from Safety Valve relief only if he “receives an
adjustment for an aggravating role under § 3B1.1.” U.S.S.G.
§ 5C1.2 cmt. n.5 (emphasis added). In other words, the Safety
Valve criterion only seems to proscribe relief for those who are
actually given an “organizer, leader, manager, or supervisor”
adjustment under the Sentencing Guidelines. That is what the
government under Paragraph Nine expressly surrendered by
forgoing its ability to argue that Moreno-Membache should
“receive” a supervisory adjustment under Section 3B1.1.
And Moreno-Membache in fact never “receive[d]” any such
adjustment under the Sentencing Guidelines.
Because the government’s ability to oppose MorenoMembache’s eligibility for Safety Valve relief on the grounds
of his supervisory or managerial status textually hinged on that
status actually being “determined” under the Sentencing
Guidelines and Moreno-Membache actually “receiv[ing]” such
an adjustment, the plea agreement, at the very least, can
reasonably be read to foreclose the government from pursuing
such an argument at sentencing.
Reinforcing our conclusion, the government candidly
acknowledged at oral argument that Paragraph Nine was
“inelegantly drafted.” Oral Arg. Tr. 21:8–9. Which seems to
be a deft way of admitting that the agreement was unclear.
Because Moreno-Membache reasonably read that inelegant
phrasing as foreclosing the government from arguing his
ineligibility for Safety Valve relief based on his asserted
supervisory or managerial status, that is the reading we must
give the agreement’s text.
The government’s only counter is to read Paragraph Nine
as simply promising that it would not seek any additional
adjustments to Moreno-Membache’s sentence. That cannot be.
Remember, Moreno-Membache’s plea agreement was a “CPlea” that, by its very terms, already precluded the government
from seeking any additional adjustments or enhancements to
Moreno-Membache’s sentence. See, e.g., Freeman, 564 U.S.
3 To be clear, whether a criminal defendant must actually
receive an aggravating role adjustment under the Sentencing
Guidelines to be ineligible for Safety Valve relief is not the question
in this case. The only question is whether Moreno-Membache
reasonably read the plea agreement that way, in light of Paragraph
Nine and the incorporated Sentencing Guidelines provision. He did.
at 529 (quoting FED. R. CRIM. P. 11(c)(1)(C)). So there was no
reason for the plea agreement to include language prohibiting
the government from seeking an adjustment under Chapter 3,
Part B of the Sentencing Guidelines other than to preclude the
government’s opposition to Safety Valve relief on the basis of
an asserted supervisory or managerial role.
In other words, the language of the plea agreement either
meant something under Moreno-Membache’s reading or meant
nothing under the government’s. We are loath to assume that
a defendant surrendered a panoply of constitutional rights in
exchange for a meaningless and valueless promise. See 11
WILLISTON ON CONTRACTS § 32:5 (4th ed. Supp. Nov. 2020)
(“An interpretation which gives effect to all provisions in the
contract is preferred to one which renders part of the writing
superfluous, useless, or inexplicable.”); cf. United States v.
Franco-Lopez, 312 F.3d 984, 991 (9th Cir. 2002) (“[W]e prefer
a contractual interpretation that gives some effect to the
government’s apparent promises contained in the
agreement[.]”). At a minimum, whether the government’s
promise was meaningful or meaningless is textually
Of course, Paragraph Nine’s language cannot be read in
isolation. Because a plea agreement is a contract, it must be
read as a whole. United States v. Schwartz, 511 F.3d 403, 405
(3d Cir. 2008) (Plea agreements “must be interpreted as a
whole and no part should be ignored.”) (quoting CALAMARI &
PERILLO, CONTRACTS §3.13 (5th ed. 2003)); see also 11
WILLISTON ON CONTRACTS §32:5 (4th ed. Supp. Nov. 2020).
In that regard, the district court pointed to two other provisions
in the agreement that, in its view, preserved the government’s
ability to oppose Safety Valve relief on the basis of Moreno-
Membache’s asserted supervisory or managerial status.
Neither provision resolves, nor even addresses, the relevant
The district court pointed to Paragraphs Eight and Twelve
of the agreement, both of which preserved the government’s
ability to advise the court of “facts pertinent to the sentencing
process,” J.A. 132 ¶ 8, and “facts material to sentencing,”
J.A. 133 ¶ 12. But those provisions are more naturally read as
allowing the government to introduce evidence bearing on
those other sentencing and Safety Valve factors not expressly
waived in Paragraph Nine. That, in fact, is exactly what the
government has done in arguing that Moreno-Membache is
ineligible for the Safety Valve because of his possession of a
firearm to facilitate the offense.
The district court offered a second rationale for finding
that the plea agreement was unambiguous. It reasoned that the
Sentencing Guidelines commentary defining an “organizer,
leader, manager, or supervisor” as a person “who receive[d] an
adjustment for an aggravating role” does not limit the court’s
ability to determine Safety Valve eligibility because the court,
“not the government, makes the final determination of the
applicability of such a role enhancement.” See MosqueraMurillo, 2018 WL 6267765, at *6. So in the district court’s
view, the government’s promise not to present evidence did not
prevent the court itself from finding that a role enhancement
applied. See id. Maybe. But the issue here is not about the
power of the court, but whether the government’s conduct
breached the plea agreement when it asked the court to find that
Moreno-Membache was a supervisor or manager as part of the
sentencing proceeding and submitted evidence to that end on
which the court relied. Or, more specifically, whether the plea
agreement’s ambiguous language could reasonably be
understood by Moreno-Membache as foreclosing that
argument and introduction of evidence by the government.
In sum, based on the plain text of the plea agreement, the
correlative wording of the Sentencing Guidelines, and the
longstanding rule that ambiguity in a plea agreement is
interpreted against the government, we hold that the
government breached its agreement with Moreno-Membache
when it argued that he was ineligible for Safety Valve relief
because of any supervisory or managerial role he might have
played in the offense. With so much at stake for the defendant,
it is not too much to hold the government that drafted the plea
agreement responsible for the misunderstanding that arose
from a confusing, unclear (“inelegant”), and “unnecessary”
hollow promise in the agreement, Oral Arg. Tr 21:8–9, 17:1–3.
The government argues that, regardless of his supervisory
or managerial status, Moreno-Membache is still ineligible for
Safety Valve relief because he “possess[ed] a firearm or other
dangerous weapon” in connection with the conspiracy, see 18
U.S.C. § 3553(f)(2).
Specifically, the government argued to the district court
that Moreno-Membache was ineligible for Safety Valve relief
because he attended one Mistby planning meeting with a
9-millimeter pistol. The government supported this account
with the testimony of a special agent who reviewed transcripts
of interviews with the Mistby’s captain (a cooperating coconspirator), who stated he saw the firearm, and a crewmember
(another cooperating co-conspirator), who asserted he saw
what appeared to be the outline of a gun in MorenoMembache’s waistband. J.A. 226–227.
But to render a defendant ineligible for relief, his
possession of the firearm must have had “the potential of
facilitating the drug trafficking offense.” United States v.
Erazo, 628 F.3d 608, 611 (D.C. Cir. 2011) (alteration omitted)
(quoting United States v. DeJesus, 219 F.3d 117, 122 (2d Cir.
2000)); see 18 U.S.C. § 3553(f)(2) (firearm must be possessed
“in connection with the offense”).
In this case, the district court grounded its finding of
facilitation on Moreno-Membache’s “supervisory role”
guarding the narcotics. Mosquera-Murillo, 2019 WL 3037533,
at *16. Specifically, the district court found that MorenoMembache “had responsibility for supervising others in the
storage and movement of the cocaine that ultimately was
loaded onto the Mistby.” Id. at *14. The district court therefore
found that, because Moreno-Membache played a supervisory
role in safeguarding the cocaine and possessed a firearm, his
firearm had the potential of facilitating the drug trafficking
offense. See id. at *16; see also Erazo, 628 F.3d at 611.
Because the district court specifically tied its facilitation
determination to its prior finding that Moreno-Membache acted
as a manager or supervisor, we are unable to disentangle the
district court’s firearm determination from the government’s
arguments in breach of the plea agreement asserting MorenoMembache’s supervisory or managerial position. As a result,
“the interests of justice and appropriate recognition of the
duties of the prosecution in relation to promises made in the
negotiation of pleas of guilty will be best served by remanding
the case[.]” Santobello, 404 U.S. at 262; see Pepper v. United
States, 562 U.S. 476, 507 (2011) (“Because a district court’s
‘original sentencing intent may be undermined by altering one
portion of the calculus,’ an appellate court when reversing one
part of a defendant’s sentence ‘may vacate the entire sentence
so that, on remand, the trial court can reconfigure the
sentencing plan[.]’”) (formatting modified; first quoting United
States v. White, 406 F.3d 827, 832 (7th Cir. 2005), then quoting
Greenlaw v. United States, 554 U.S. 237, 253 (2008)); United
States v. Wolff, 127 F.3d 84, 86 (D.C. Cir. 1997).
The dissenting opinion asserts that the district court’s
analysis of Moreno-Membache’s firearm and his supervisory
role were sufficiently distinct because, if Moreno-Membache
guarded the cocaine while possessing a firearm, it would not
matter if he was a lowly laborer in the conspiracy or a kingpin.
Dissenting Op. 3–4. While we agree on the law, we disagree
on the facts. When it found that Moreno-Membache guarded
drugs, the district court expressly predicated its determination
upon its specific finding that Moreno-Membache “had a
supervisory role,” Mosquera-Murillo, 2019 WL 3037533,
at *16, an issue it likely would not have reached had the
government complied with the plea agreement.
The dissenting opinion separately contends that the
firearm could be connected to the offense because one
cooperating co-conspirator claimed to have seen MorenoMembache with a pistol at a planning meeting and another
cooperating co-conspirator said that he saw what he perceived
to be the outline of a pistol in Moreno-Membache’s waistband
at the Mistby’s launch site. But that was not the basis for the
district court’s facilitation finding. And this court is illequipped to make such a factual finding.4
4 Cf. United States v. Vaval, 404 F.3d 144, 155 (2d Cir. 2005)
(remanding for resentencing even though the district court was not
influenced by the government’s breach of the plea agreement
because, “in order to preserve the integrity of plea bargaining
procedures and public confidence in the criminal justice system, a
defendant is generally entitled to the enforcement of a plea
Remand will allow the district court to make an
independent determination regarding the firearm criterion,
uninfluenced in any way by any of the government’s improper
argument or evidence presented to support MorenoMembache’s asserted supervisory or managerial status. More
to the point, on remand Moreno-Membache will finally receive
what he bargained for—a sentencing hearing freed of the
government’s argument or evidence that he was a manager or
supervisor in the conspiracy.
Outcome: For all of those reasons, we reverse the ruling of the district
court, vacate Moreno-Membache’s sentence, and remand to the
district court for further proceedings consistent with this