• Judge Alvin Hellerstein indicated President Donald Trump waited too long to seek federal court intervention after his May 2024 state court conviction
• The 92-year-old jurist characterized Trump’s legal maneuvers as seeking “two bites at the apple” by first litigating in state court
• Trump was convicted on 34 felony counts of falsifying business records related to hush money payments to Stormy Daniels

NEW YORK (TDR) — U.S. District Judge Alvin K. Hellerstein signaled Wednesday he will likely reject President Donald Trump‘s attempt to void his 34 felony convictions, slamming the president’s lawyers for waiting too long to seek federal court relief and accusing them of attempting to secure “two bites at the apple.” The 92-year-old jurist, appointed by President Bill Clinton, heard nearly three hours of arguments regarding Trump’s bid to move his hush money conviction from state to federal court, where he hoped to leverage presidential immunity arguments to erase the historic verdict.

Trump was convicted on May 30, 2024, in New York State Supreme Court on 34 felony counts of falsifying business records, becoming the first former U.S. president convicted of felony crimes. The charges stemmed from a $130,000 payment to adult film actress Stormy Daniels arranged by Trump’s former attorney Michael Cohen to silence her allegations of a sexual encounter during the final weeks of the 2016 presidential campaign. Judge Juan Merchan subsequently sentenced Trump to an unconditional discharge on Jan. 10, 2025, leaving the felony conviction intact while imposing no prison time, fines, or probation.

Did Hellerstein Criticize Trump’s Legal Strategy?

During the hearing in the U.S. District Court for the Southern District of New York, Hellerstein repeatedly interrupted Trump attorney Jeffrey Wall to challenge the sequencing of the president’s legal arguments. The judge took particular issue with Trump’s decision to first seek relief in state court following the U.S. Supreme Court‘s July 1, 2024, presidential immunity ruling, then pivot to federal court nearly two months later.

“You didn’t have to do that. You could have come right to the federal court. Just by filing a notice of removal, there would be no sentencing. You made a choice, and you sought two bites at the apple.” — Judge Alvin Hellerstein, U.S. District Court for the Southern District of New York, Feb. 4

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The Supreme Court’s immunity decision, issued in Trump v. United States, established that former presidents enjoy absolute immunity from criminal prosecution for official acts within their core constitutional authority and at least presumptive immunity for other official acts. However, the Court left open whether specific conduct constitutes official or unofficial acts, remanding that determination to lower courts.

Hellerstein previously denied Trump’s pretrial removal request in September 2023 and rejected a post-conviction removal bid in September 2025, finding the conduct involved personal rather than official presidential actions. The 2nd U.S. Circuit Court of Appeals vacated that latter ruling in November 2025, directing Hellerstein to reconsider whether evidence admitted at trial related to official acts and, if so, whether that transformed the case into one properly removable to federal court.

What Evidence Is at the Center of the Dispute?

Trump’s legal team argued that prosecutors improperly introduced evidence covered by presidential immunity, including Oval Office conversations with then-White House Communications Director Hope Hicks, social media posts regarding Cohen, and testimony from former White House aide Madeleine Westerhout. Wall contended that once this evidence was admitted, “this became a prosecution relating to those official acts,” according to ABC News.

“The telling part of the evidence was the falsification of the records themselves that had nothing to do with any kind of White House directory or official records.” — Judge Alvin Hellerstein, challenging the defense theory, Feb. 4

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Steven Wu, representing the Manhattan District Attorney’s Office, countered that the Supreme Court opinion affects only evidence admissibility, not the underlying charges, which he said had nothing to do with Trump’s official conduct. Wu argued that introducing evidence of official acts does not transform a criminal action into one involving official acts, per Courthouse News.

“Defendant seems to think if evidence of official acts is introduced, that somehow transforms the criminal action. That is just not true.” — Steven Wu, Manhattan District Attorney’s Office, Feb. 4

Wall defended the timing of the federal court filing, arguing that Trump’s team faced a compressed schedule with sentencing looming just 10 days after the Supreme Court ruling. He maintained that seeking state court relief first represented what “any sensible litigant would do” to avoid showing disrespect to the trial judge. Hellerstein flatly rejected this characterization.

“Not so. That is a decision on your part. Whether Judge Merchan would have been pleased or displeased is totally irrelevant. You intended to litigate in state court. Only when you sensed disappointment did you revert to an effort to have a federal forum.” — Judge Alvin Hellerstein, Feb. 4

Why Can’t Trump Pardon Himself in This Case?

The president’s pursuit of federal court jurisdiction carries significant strategic implications. While Trump cannot pardon himself for a state conviction under the U.S. Constitution’s structural limitations, transferring the case to federal court would allow him to seek dismissal on immunity grounds and potentially secure an expedited path to the Supreme Court. Normally, removal requests must be filed within 30 days of arraignment, though federal courts have recognized limited exceptions for “good cause” under 28 U.S.C. § 1443.

Hellerstein expressed skepticism about the propriety of moving a case to federal court after a state jury has already rendered a verdict, sentencing has occurred, and a state appeal is pending. The judge questioned whether simply adopting the state court judgment and certifying it for federal appellate review constitutes an appropriate exercise of federal jurisdiction.

“The only thing you want me to do is adopt the New York Supreme Court judgment as mine. In conscience I can’t do that.” — Judge Alvin Hellerstein, Feb. 4

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