Medina v. United States

Background

Hector Medina, representing himself, sought relief under 28 U.S.C. § 2255, a procedure that allows a federal prisoner to challenge a sentence on specified legal or constitutional grounds. He claimed that his lawyers provided ineffective assistance in violation of the Sixth Amendment.

Medina had been charged with conspiracy to distribute one kilogram or more of heroin and possession with intent to distribute heroin. He pleaded guilty to both counts on January 5, 2017, under a plea agreement. On June 19, 2017, the court imposed a principal sentence of 240 months in prison, which was below the applicable guideline range. The Second Circuit later affirmed the judgment.

Several lawyers represented Medina at different stages. The first was appointed before indictment, later withdrew after Medina retained counsel, and represented Medina during the pre-indictment phase. A second retained lawyer also withdrew. A third lawyer was appointed and represented Medina during his guilty plea, sentencing, and appeal.

Claims and analysis

Medina asserted three ineffective-assistance claims.

Advice to participate in proffer sessions. Medina argued that his first lawyer should have investigated and disclosed a government policy against making cooperation agreements with people who had previously cooperated and then committed additional crimes. The lawyer stated that Medina wanted to seek a cooperation agreement, that he warned Medina there was no guarantee one would result, and that Medina’s prior cooperation and later arrest made an agreement less likely. The written proffer agreement also said it was not a cooperation agreement and that the government made no representation about the likelihood of reaching one.

The court concluded that the lawyer exercised reasonable professional judgment in advising Medina to participate. The lawyer had a basis for believing that cooperation might still be possible and that attempted cooperation could help at sentencing even without a cooperation agreement. The court also found no prejudice—a reasonable probability that the alleged error changed the result—because Medina did not show that he would have gone to trial, that his proffer statements were used against him, or that they produced additional evidence affecting the case.

Plea negotiations. Medina argued that his first lawyer had discussed a better plea arrangement that would not involve a ten-year mandatory minimum sentence. The lawyer stated that he had discussed a possible plea with a sentencing range of six or seven years, but both the government and the lawyer stated that no formal plea offer had been made. The court found that Medina had not identified a specific unreasonable act or omission by the lawyer. It also found no indication that the government would have made, or the court would have accepted, a plea agreement producing a lower sentence.

Sentencing and the Ex Post Facto Clause. Medina argued that his third lawyer failed to adequately research and present an argument that applying the 2016 version of the Sentencing Guidelines violated the Ex Post Facto Clause, which generally restricts retroactive increases in criminal punishment. The court found that the lawyer had in fact identified and argued the issue at sentencing. It further concluded that the argument could not have changed the result because the conduct underlying Medina’s current convictions occurred after the relevant November 2007 Guidelines amendments. The court and the Second Circuit had already rejected the argument.

Disposition

Judge P. Castel denied Medina’s § 2255 petition. The court directed the Clerk to close case 19-cv-10724 and terminate the related motion in criminal case 15-cr-778. It also directed the government to mail Medina copies of the unreported decisions cited in the order.

The court declined to issue a certificate of appealability because Medina had not made a substantial showing that a constitutional right was denied. The court also certified that an appeal would not be taken in good faith and denied permission to proceed without paying the filing fee for purposes of an appeal.