NEW YORK (AP) — A federal judge appeared poised to again reject President Donald Trump’s bid to erase his hush money conviction, slamming his lawyers Wednesday for legal maneuvers he said amounted to taking “two bites at the apple.”
Directed by an appeals court to take a fresh look at the matter, Judge Alvin K. Hellerstein was at turns inquisitive and incredulous in nearly three hours of arguments in Manhattan federal court. Sparring with Trump lawyer Jeffrey Wall throughout, he suggested the whole exercise was moot because the president’s legal team had waited too long after the historic verdict to seek federal court relief.
The 2nd U.S. Circuit Court of Appeals in November ordered Judge Hellerstein to reconsider his earlier decision to keep the New York case in state court instead of moving it to federal court, where Trump can seek to have it thrown out on presidential immunity grounds.
A three-judge panel ruled Hellerstein erred in his September 2025 ruling by failing to consider “important issues relevant” to Trump’s request to move the case to federal court. But they expressed no view on how he should rule.
Trump, a Republican, did not attend Wednesday’s arguments.
Hellerstein heard from Wall and Steven Wu, a lawyer from the Manhattan district attorney’s office, which prosecuted the case and wants it to remain in state court.
Hellerstein thanked both men for their "very provocative arguments” and said he would issue a ruling at a later date.
Trump was convicted in state court
Trump was convicted in May 2024 of 34 felony counts of falsifying business records to conceal a hush money payment to adult film actor Stormy Daniels, whose allegations of an affair with Trump threatened to upend his 2016 presidential campaign. He was sentenced to an unconditional discharge, leaving his conviction intact but sparing him any punishment.
Trump denies Daniels’ claim and said he did nothing wrong. He has asked a state appellate court to overturn the conviction.
Hellerstein interrupted Wall almost as soon as Wednesday’s arguments began, injecting his thoughts and questions and telling the lawyer “I think I have to quarrel with you a bit” about the sequence of events that followed Trump’s conviction in May 2024.
The judge took issue with the Trump legal team’s decision making after the verdict and a subsequent U.S. Supreme Court ruling that presidents and former presidents cannot be prosecuted for official acts.
Instead of immediately seeking to move the case to federal court, Trump’s lawyers first asked the trial judge, Juan Merchan, to throw out the verdict on immunity grounds.
Wall argued that Trump’s lawyers were in a time crunch after the Supreme Court’s July 1, 2024, ruling because Trump's sentencing was scheduled for just 10 days later. Had Trump’s lawyers sought to bring the case to federal court at that point, the district attorney’s office, which prosecuted the case, may have criticized that as premature, Wall said.
Trump’s lawyers did not ask Hellerstein to intervene until nearly two months later. The judge on Wednesday called that a “strategic decision" and suggested that by going to the state court first, Trump’s lawyers cost him the right to pursue remedies in federal court.
“No, your honor,” Wall said. “It is what any sensible litigant would do” in that situation.
“Not so,” Hellerstein replied.
“That is a decision on your part," the judge added. “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.”
Trump’s lawyers “made a choice," Hellerstein said, "and you sought two bites at the apple.”
Normally, such a request must be made within 30 days of an arraignment, but a federal appeals court in Washington, D.C. has ruled that exceptions can be made if “good cause” is shown.
Wu concurred that Wall’s argument “confirms this was a strategic choice by the defendants.”
He also said Trump’s lawyers knew they could have simultaneously submitted arguments or a letter to Merchan and still sought to transfer the case to federal court. Past rulings have made clear that “you cannot go to state court and when you’re unhappy, then go to federal court,” Wu said.
Previous requests to move the case were denied
Hellerstein, who was nominated by Democratic President Bill Clinton, has twice denied Trump’s requests to move the case. The first was after Trump’s March 2023 indictment; the second was the post-verdict ruling at issue at Wednesday’s hearing.
In that ruling, Hellerstein said Trump’s lawyers had failed to meet the high burden of proof for changing jurisdiction and that Trump’s conviction for falsifying business records involved his personal life, not official actions that the Supreme Court ruled are immune from prosecution.
The 2nd Circuit panel said Hellerstein’s ruling, which echoed his pre-trial denial, “did not consider whether certain evidence admitted during the state court trial relates to immunized official acts or, if so, whether evidentiary immunity transformed” the hush money case into one that relates to official acts.
The three judges said Hellerstein should closely review evidence Trump claims relate to official acts.
If Hellerstein finds the prosecution relied on evidence of official acts, the judges said, he should weigh whether Trump can argue those actions were taken as part of his White House duties, whether Trump “diligently sought” to have the case moved to federal court and whether the case can even be moved to federal court now that Trump has been convicted and sentenced in state court.