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D.C. Circuit: Government Breached Plea Agreement by Violating Ambiguous Terms, Ambiguities Resolved in Favor of Defendants, Sentence Vacated

by David M. Reutter

The U.S. Court of Appeals for the District of Columbia Circuit held that a plea agreement was ambiguous as to the Government’s ability to oppose Safety Valve relief on grounds the defendant was a supervisor or manager in a drug conspiracy. It ordered resentencing that was untainted and uninfluenced by the Government’s evidence on that issue.

The Court’s opinion was issued in an appeal brought by Antonio Moreno-Membache. The case stemmed from a drug bust made in June 2012 by the U.S. Coast Guard. They interdicted a “go-fast boat” off the coast of Panama and retrieved the cargo the crew threw overboard, which amounted to more than 220 kilograms of cocaine and more than 235 kilograms of marijuana.

Moreno-Membache was not a member of the boat’s crew. He was indicted to the U.S. and extradited from Colombia after a joint investigation between the two governments. In January 2016, Moreno-Membache pleaded guilty to conspiracy to “knowingly and intentionally 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 of marijuana or more.

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 carried a mandatory most minimum sentence of 10 years in prison. At issue on appeal was a separate statutory provision, known as the Safety Valve, 18 U.S.C. § 3553(f), that allows the district court to approve sentences below the mandatory minimum in certain circumstances.

To obtain Safety Valve relief, 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 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. § 3553(f)(1)-(5).

The final aspect of the case relevant to the appeal was the fact Moreno-Membache entered into a “C-Plea,” which 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 (2011) (quoting Fed. R. Crim. P. 11(c)(1)(C)). Under the agreement between Moreno-Membache and the Government, the maximum sentence was agreed to as 120 months, but the district court could impose a lesser sentence if it determined that Moreno-Membache was eligible for Safety Valve relief.

The agreement provided that Moreno-Membache expressly preserved his right to seek relief from the mandatory minimum sentence under that provision. The Government also preserved its right to argue that (i) the Safety Valve provision is categorically inapplicable to his conviction under the Maritime Drug Act and (2) he does not meet its eligibility criteria. Yet, in that very same paragraph (“Paragraph Nine”), the Government surrendered its ability “to seek any of the adjustments set out in U.S.S.G. Chapter 3, Part B,” which contains sentencing enhancements for when a defendant plays an “aggravating role” for acting as an organizer, leader, manager, or supervisor in the criminal scheme. U.S.S.G. Manual § 3B1.2.

Initially, the district court ruled that Safety Valve relief is inapplicable to offenses under the Maritime Drug Act. However, on appeal, the D.C. Circuit reversed, holding that Safety Value relief is available for such offenses. United States v. Mosquera-Murillo, 902 F.3d 285 (D.C. Cir. 2018).

On remand, the district court turned to the five statutory criteria to determine if Moreno-Membache qualified for Safety Valve relief and summarily concluded that he clearly satisfied three of the criteria, leaving only the “organizer, leader, manager, or supervisor” and whether he possessed a weapon in conjunction with the offense criteria at issue.  

The Government argued he didn’t qualify and presented evidence from two co-conspirators that Moreno-Membache possessed a firearm at a planning meeting. It also argued, and the district court agreed, that he was a supervisor or manager of the crew members involved in the offense. The district court, therefore, found Moreno-Membache was ineligible for relief under the Safety Valve provision and sentenced him to the mandatory minimum of 120 months in prison. Moreno-Membache appealed, arguing that the Government breached the terms of his plea agreement by arguing for his leadership role despite the fact the Government surrendered the right to do so via the agreement.

The Court began its analysis by stating it applies principles of contract law in determining whether a party has breached the terms of a plea agreement. United States v. Henry, 758 F.3d 427 (D.C. Cir. 2014); United States v. Jones, 58 F.3d 688 (D.C. Cir. 1995). In addition, constitutional principles and contract law dictate that contracts (plea agreements are contracts) are construed against their drafters, and thus courts resolve any ambiguities against the Government (as drafter of the plea agreement). In re Sealed Case, 702 F.3d 59 (D.C. Cir. 2012).

The Court observed that the crux of the case is Paragraph Nine of the plea agreement, which it characterized as “at a minimum, ambiguous.” The Court stated that “Moreno-Membache reasonably read the plea agreement” as barring the Government from arguing against his eligibility for Safety Valve relief on the basis of his alleged leadership role. The Government itself bolsters that conclusion when it candidly acknowledged during oral arguments that Paragraph Nine was “inelegantly drafted,” the Court stated, adding that it “seems a deft way of admitting that the agreement was unclear.”

The Court concluded that it must read Paragraph Nine as foreclosing the Government’s ability to argue against Safety Valve relief based on Moreno-Membache’s alleged leadership role because that’s how he read it. Thus, the Court held that the Government breached the plea agreement when by arguing he was ineligible for Safety Valve relief due to his leadership role.

The Court chided: “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.”

The Government also argued that Moreno-Membache’s possession of a firearm disqualified him from Safety Valve relief. The Court agreed that may be true, but the current record entangled that issue to such an extent with the leadership issue that the Court was “unable to disentangle” the two. Consequently, “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 v. New York, 404 U.S. 257 (1971). The Court instructed that on remand the district court must make an independent determination on the firearm issue without any taint or influence of the Government’s improper leadership argument and evidence.

Accordingly, the Court reversed the district court’s ruling, vacated Moreno-Membache’s sentence, and remanded to the district court for further proceeding consistent with its opinion. See: United States v. Moreno-Membache, 995 F.3d 249 (D.C. Cir. 2021). 

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Related legal case

United States v. Moreno-Membache



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