Santiago-Ortiz v. United States

Background

Jose Santiago-Ortiz was convicted in 2018 on five counts connected to a murder committed during a narcotics conspiracy. He filed a timely motion under 28 U.S.C. § 2255, a procedure allowing a federal prisoner to challenge a conviction or sentence, raising nine grounds based primarily on alleged ineffective assistance of counsel. The motion consisted of a form with brief assertions and referred to a later legal memorandum.

The court granted six requests for extensions to file that memorandum. After the final deadline passed without a memorandum, the court dismissed the § 2255 motion on August 10, 2022, after an initial review. Six days later, the court received a memorandum signed August 4 and postmarked August 11. Applying the prison-mail rule, the court treated the memorandum as filed when Santiago-Ortiz provided it to prison officials for mailing. The court concluded that the government’s mail-log evidence did not overcome the presumption that the memorandum was received on its signing date, so it considered the memorandum and later briefing timely.

Santiago-Ortiz then asked to file a new memorandum. The court liberally interpreted that request as a motion for permission to amend or supplement the original § 2255 motion. Because the proposed memorandum would address grounds already included in the original motion, the court concluded that the amendment could relate back to the original filing. Under Federal Rule of Civil Procedure 15, courts generally allow amendments when fairness requires, but may deny an amendment that would be futile—that is, one that could not succeed.

Ground-by-Ground Rulings

- Ground I: Santiago-Ortiz claimed that trial counsel should have sought dismissal of Counts Three and Five on double-jeopardy grounds. The court denied permission to amend as futile. It reasoned that the narcotics-conspiracy count was the predicate offense for the firearm count and that there was no double-jeopardy problem from trying the relevant counts at the same time. The court dismissed Ground I and denied the § 2255 motion as to that ground. - Ground II: Santiago-Ortiz claimed that counsel should have sought dismissal of Counts Four and Five for failure to state offenses against the United States. The court granted permission to amend so he could explain the factual and legal basis for the claim. - Ground III: Santiago-Ortiz claimed that trial counsel failed to object to pervasive prosecutorial misconduct. The court denied permission to amend as futile, relying on its prior conclusion that there had been no prosecutorial misconduct at the trial. - Grounds IV and V: He claimed that counsel failed to investigate and prepare adequately and failed to call requested defense witnesses. Because he had not identified what counsel failed to do, who the witnesses were, or what they would have said, the court granted one final opportunity to amend and supply those details. - Ground VI: He claimed that counsel improperly conceded that he committed the murder. The court concluded that the ineffective-assistance claim failed because the trial outcome would not have been different given the evidence that he killed Jerry Tide. It also rejected the proposed argument based on the Supreme Court’s decision in McCoy v. Louisiana, concluding that counsel had not conceded guilt of any charged crime and that McCoy was not retroactively applicable on this collateral challenge. The court denied permission to amend as futile. - Ground VII: He claimed that counsel failed to conduct plea negotiations. The record showed that the government had made a plea offer, that Santiago-Ortiz had discussed it with counsel, understood it, and rejected it. The court also rejected related arguments concerning sentencing advice and a possible counteroffer. It denied permission to amend as futile and dismissed Ground VII in its entirety. - Ground VIII: He claimed that counsel failed to object to the jury instructions. The court granted permission to amend so he could provide factual and legal support and explain how the alleged failure affected the outcome. - Ground IX: He claimed that appellate counsel was ineffective for failing to raise Grounds I through VII on appeal. The court granted permission to amend only to the extent that permission was granted on the underlying grounds. It dismissed the portion tied to grounds that were otherwise dismissed and denied permission to amend those portions as futile.

Disposition

The court denied Santiago-Ortiz’s § 2255 motion as to Grounds I, III, VI, VII, and part of IX. It granted his motion for permission to amend as to Grounds II, IV, V, VIII, and part of IX. The amended memorandum was due June 30, 2023; the government’s response was due July 31, 2023; and any reply was due August 15, 2023. The court denied a certificate of appealability as to the denied grounds and certified that an appeal from those rulings would not be taken in good faith. Judge Lewis A. Kaplan also reminded Santiago-Ortiz that a non-lawyer inmate may assist him but may not represent him.