by David M. Reutter

The U.S. Court of Appeals for the First Circuit vacated a defendant’s guilty plea because it was entered without an understanding of the consequences. The basis for the Court’s ruling rested upon the U.S. District Court for the District of Puerto Rico and plea agreement indicating an award for prison credit on a state charge for which the defendant could not, and did not, receive due to mandatory sentencing provisions.

Before the Court was the appeal of Samuel Arce-Ayala, who pleaded guilty to federal charges for conspiring to possess with the intent to distribute controlled substances and possessing a firearm in furtherance of a drug trafficking crime. “Arce-Ayala was a leader, drug point owner, and enforcer for ‘Los Menores,’ a violent drug trafficking organization in Puerto Rico,” the Court wrote.

Five years before his 2017 federal indictment, Arce-Ayala was convicted in the Commonwealth of Puerto Rico on two counts of attempted second-degree murder and three firearm offenses that involved Los Menores activities. Arce-Ayala was sentenced to eight years imprisonment for those convictions. Under the federal plea agreement, Arce-Ayala agreed to plead guilty to the two charged offenses in return for a sentence both parties would recommend.

The drug trafficking conspiracy charge carried a minimum term of 120 months imprisonment with a maximum term of life in prison. 21 U.S.C. §§ 841(b)(1)(A), 860. The firearms charge carried a minimum sentence of 60 months with a maximum term of life. 18 U.S.C. § 924(c)(1)(A). The parties agreed to recommend on Count I the statutory minimum sentence of 120 months and as to Count II, the statutory minimum of 60 months was agreed upon. It was further agreed that the Commonwealth convictions constituted “relevant conduct to the case of reference and that in the instant case, the sentence of imprisonment shall be imposed pursuant to U.S.S.G § 5G1.3 and § 5K2.23.”

At the plea hearing, the prosecutor explained to the District Court the plea agreement upon which the parties agreed. A colloquy conducted by the court asked Arce-Ayala if he understood “that whatever time you spent in the State Court will be – you will be given credit for that time when I sentence you in this case.” The court accepted the guilty pleas and scheduled a sentencing hearing.

Subsequent to the plea acceptance, Arce-Ayala’s defense attorney learned the “relevant conduct” provision could not provide Arce-Ayala with credit for time served in Commonwealth custody. Generally, “sentencing guidelines cannot be employed to impose a sentence below an applicable statutory mandatory minimum.” United States v. Ramirez, 252 F.3d 516 (1st Cir. 2001) (citing Melendez v. United States, 518 U.S. 120 (1996)). Only two ways exist to reduce a mandatory minimum sentence: (1) providing substantial assistance under 18 U.S.C. § 3553(e) or Federal Rule of Criminal Procedure 35(b) or (2) conviction of a drug trafficking offense that meets the requirements of the “safety valve” provision in 18 U.S.C. § 3553(f). See United States v. Candelario-Ramos, 45 F.4th 521 (1st Cir. 2022).

Arce-Ayala did not qualify under either of those provisions. In a footnote, the Court noted that the Ramirez Court ruled that credit for time served on a non-discharged sentence can be given so long as the total of the credit and “reduced federal sentence equals or exceeds the statutory mandatory minimum period.” At the time Arce-Ayala was federally sentenced, he was ineligible because he was discharged from the Commonwealth sentence.

Attempts to withdraw the plea failed in the District Court, and the prosecutor rejected overtures to make concessions to satisfy the spirit of the agreement. The District Court sentenced Arce-Ayala to 120 months on the drug trafficking conspiracy offense and 60 months on the firearms offense to be served consecutively. Arce-Ayala timely appealed his conviction.

The Court began its analysis by noting that a defendant may withdraw a guilty plea prior to sentencing if he can demonstrate “a fair and just reason for requesting the withdrawal.” See Fed. R. Crim. P. 11(d)(2)(B). The standard for withdrawal is “liberal,” United States v. Kobrosky, 711 F.2d 449 (1st Cir. 1983), and “permissive.” United States v. Merritt, 755 F.3d 6 (1st Cir. 2014). But there is no “unfettered right to retract a guilty plea.” United States v. Flete-Garcia, 925 F.3d 17 (1st Cir. 2019).

In determining whether a defendant has demonstrated a “fair and just reason” to withdraw a guilty plea, courts consider: “(1) whether the original plea was knowing, intelligent, and voluntary and in compliance with Rule 11, (2) the strength of the reason for withdrawal, (3) the timing of the motion to withdraw, (4) whether the defendant has a serious claim of actual innocence, (5) whether the parties had reached (or breached) a plea agreement, and (6) whether the government would suffer prejudice if withdrawal is permitted.” United States v. Gardner, 5 F.4th 110 (1st Cir. 2021).

The Court distilled the plea-withdrawal inquiry down to three “core concerns” of Rule 11: (1) “a lack of coercion,” (2) “the defendant’s understanding of the charges against him,” and (3) “the defendant’s knowledge of the consequences of the guilty plea.” United States v. Williams, 48 F.4th 1 (1st Cir. 2022). Failure to satisfy any of the three concerns “requires the guilty plea be set aside.” United States v. Isom, 85 F.3d 831 (1st Cir. 1996). The plea-withdrawal inquiry is fact-intensive. See United States v. Caramadre, 807 F.3d 359 (1st Cir. 2015).

Turning to the present case, the Court stated that Arce-Ayala’s case implicated the third concern. The Court determined that both the District Court’s statements and defense counsel’s advice reasonably led Arce-Ayala to understand that his federal sentence would be reduced by his state sentence, regardless of the applicable mandatory minimum terms, pursuant to the “relevant conduct” provision in the plea agreement.

During the change-of-plea hearing, the District Court explained to Arce-Ayala that the “relevant conduct” provision meant that he “will be given credit” for “whatever time [he] spent in the State Court” when sentenced in the federal case. The Court concluded that Arce-Ayala could reasonably interpret the District Court’s explanation “as a guarantee that he would receive credit for this time served in state custody” because it didn’t contain any “conditions or reservations.” (See full opinion for the extended dialogue between the District Court judge and Arce-Ayala that convinced the Court that Arce-Ayala did not meaningfully understand the consequences of his plea.)

Additionally, the Court stated that he was “particularly susceptible” to understanding the District Court’s explanation as a guarantee because his lawyer had provided him with incorrect legal advice earlier regarding the effect of the “relevant conduct” provision. Thus, the Court ruled that he lacked sufficient knowledge of the consequences of his guilty plea and that his plea violated a “core concern” of Rule 11.

Accordingly, the Court vacated the judgment and remanded for further proceedings that permit Arce-Ayala to withdraw his guilty plea. See: Untied States v. Arce-Ayala, 91 F.4th 28 (1st Cir. 2024).

Related legal case