United States v. Alexander Ramirez-Figueredo, 33 F.4th 312

Alexander Ramirez‑Figueredo, a Cuban national, had an extensive state criminal record before his first federal prosecution.
In 2020 police found ~0.5 kg of methamphetamine and ~1 kg of heroin on him; after a Miranda warning he confessed intent to distribute and ties to a cartel.
He pleaded guilty in federal court to possession with intent to distribute methamphetamine under a written plea agreement that recited his and counsel’s acknowledgment that counsel had advised him of rights and consequences.
At the change‑of‑plea colloquy the district court complied with most Rule 11 requirements but did not give the Rule 11(b)(1)(O) immigration warning that a plea "may" have immigration consequences.
At sentencing the court imposed 192 months’ imprisonment; defendant claimed pre‑ and post‑arrest cooperation (no 5K1.1 or Rule 35 motion was filed) and argued on appeal that (1) the missing Rule 11 warning requires vacatur of the plea and (2) the court failed to consider his cooperation at sentencing.

Issue	Plaintiff's Argument	Defendant's Argument	Held
Failure to give Rule 11(b)(1)(O) immigration warning — plain error	Ramirez‑Figueredo: omission prejudiced him; he would have gone to trial to avoid deportation	United States: omission was harmless; Ramirez‑Figueredo was already deportable and plea was otherwise knowing	No reversible error. Plain‑error prongs met but no prejudice: overwhelming evidence of guilt, prior deportability, signed plea showing counsel advised him, and heavy downside risk at trial meant no reasonable probability he would have pleaded differently
District court failed to consider defendant’s cooperation at sentencing (procedural reasonableness)	Ramirez‑Figueredo: court ignored or misunderstood its discretion to consider cooperation and future Rule 35 relief	United States: court considered the limited, uncorroborated cooperation and correctly declined to consider any premature Rule 35 motion	Sentence affirmed as procedurally reasonable. Court considered cooperation evidence on the record; comment about giving "no consideration" to a Rule 35 motion was a correct effort to avoid premature consideration

United States v. Vonn, 535 U.S. 55 (plain‑error review applies to unpreserved Rule 11 claims)
Greer v. United States, 141 S. Ct. 2090 (plain‑error framework for Rule 11 omissions)
Rosales‑Mireles v. United States, 138 S. Ct. 1897 (plain‑error standard elaboration)
Puckett v. United States, 556 U.S. 129 (difficulty of meeting plain‑error standard)
Dominguez Benitez v. United States, 542 U.S. 74 (prejudice standard for accepting pleas)
Lee v. United States, 137 S. Ct. 1958 (factors for assessing whether Rule 11 error affected plea decision)
INS v. St. Cyr, 533 U.S. 289 (context on immigration consequences of pleas)
Ataya v. United States, 884 F.3d 318 (6th Cir. decision on Rule 11(b)(1)(O) omission)
Padilla v. Kentucky, 559 U.S. 356 (counsel’s duty to advise about deportation risk)
El‑Nobani v. United States, 287 F.3d 417 (Fifth Amendment not require advising on collateral immigration consequences)
Gall v. United States, 552 U.S. 38 (procedural reasonableness in sentencing)
Chavez‑Meza v. United States, 138 S. Ct. 1959 (explanation required depends on circumstances)
Rita v. United States, 551 U.S. 338 (adequacy of sentencing explanation varies)
United States v. Massey, 663 F.3d 852 (Rule 35 timing; district court should not prematurely consider Rule 35 relief)