Santana v. United States

Background

Shajohnny Santana was charged in 2017 with racketeering conspiracy, drug-trafficking conspiracy, and firearm offenses. He had previously been acquitted in an earlier related criminal case. Santana moved to dismiss the new indictment on double-jeopardy grounds, but withdrew that motion after pleading guilty to racketeering conspiracy. In exchange, the Government dismissed the drug-trafficking and firearm charges at sentencing.

The court sentenced Santana to 120 months in prison on December 19, 2018. After sentencing, Santana asked to withdraw his guilty plea and sought removal of his attorney, Harvey Fishbein. The court rejected the plea-withdrawal request for jurisdictional reasons, relieved Fishbein, and appointed Lorraine Gauli-Rufo as new counsel. The Second Circuit later affirmed Santana’s sentence.

Santana then filed a petition under 28 U.S.C. § 2255, a procedure allowing a federal prisoner to challenge a conviction or sentence. He claimed ineffective assistance of counsel, meaning that his attorneys’ representation fell below constitutional standards and harmed him. His claims concerned three issues: Fishbein allegedly pressured him into pleading guilty and misled him about his sentence; Fishbein and Gauli-Rufo allegedly failed to preserve or pursue the double-jeopardy claim; and Gauli-Rufo allegedly failed to appeal the denial of his request to withdraw the guilty plea. Santana was representing himself in this proceeding.

Legal standard

The court applied the two-part test from Strickland v. Washington. Santana had to show both that his attorneys’ performance was objectively unreasonable and that the deficient performance caused prejudice. In the guilty-plea context, he also had to show a reasonable probability that, without the alleged errors, he would have rejected the plea and either gone to trial or pursued an available defense.

Guilty-plea advice

The court rejected Santana’s claim that Fishbein coerced him into pleading guilty. Santana’s allegations primarily described pressure from family members, and the court held that an attorney is not ineffective for involving family members in discussions about whether a guilty plea is in the defendant’s interest. The court also found that Santana had not provided specific facts supporting his broader allegations of coercion or misrepresentation.

The court relied on Santana’s sworn statements during the plea hearing. He said that he was satisfied with Fishbein’s representation, understood that the sentencing guidelines were not binding, understood that the court could impose a sentence above the advisory guideline range, and knew that the offense carried a possible sentence of up to 20 years. Although Santana alleged that Fishbein promised a sentence of time served, the court held that Santana’s understanding of the actual sentencing possibilities defeated his claim that counsel’s advice was constitutionally deficient.

The court separately held that Santana had not shown prejudice. His proposed alternative—going to trial—would have exposed him to mandatory minimum sentences on the dismissed drug and firearm charges, including a consecutive firearm sentence. The court also found that the double-jeopardy defense Santana identified as an alternative lacked merit.

Double-jeopardy claim

The court held that counsel was not ineffective for failing to preserve or pursue the double-jeopardy argument. It explained that two conspiracy offenses are the same in fact only when they involve a single agreement. In an earlier related proceeding involving the same underlying events, the court had found that the pharmacy-burglary conspiracy and the conspiracy charged in Santana’s case involved distinct agreements. The pharmacy case concerned nonviolent pharmacy burglaries, while the later case concerned armed invasions of drug dealers’ homes to obtain drugs.

The court concluded that any double-jeopardy challenge to the narcotics conspiracy would have failed because the agreements were factually different. A challenge to the racketeering and firearm charges also would have failed because those charges were legally distinct from the earlier charges. The court therefore held that neither Fishbein’s failure to preserve the argument nor Gauli-Rufo’s failure to raise it on appeal constituted ineffective assistance. It also stated that, after a valid guilty plea, advice that a double-jeopardy claim could not be raised on direct appeal was legally sound.

Failure to appeal plea-withdrawal denial

The court rejected Santana’s claim that Gauli-Rufo was ineffective for not appealing the denial of his request to withdraw the guilty plea. The court found that an appeal based on coercion would have been meritless because Fishbein’s representation was not ineffective. It also noted that claims alleging ineffective assistance generally are disfavored on direct appeal and are ordinarily raised through a later collateral challenge.

Disposition

The court held that Santana had not shown either constitutionally deficient performance or prejudice. It therefore denied his § 2255 petition. The court also certified under 28 U.S.C. § 1915(a)(3) that any appeal would not be taken in good faith and denied permission to appeal without paying filing fees. The Clerk was directed to terminate the open motion and mail Santana a copy of the opinion.