‘You’ve got two bites at the apple’

A federal judge cast doubt on President Donald Trump’s reasoning for trying to move his appeal of his hush money conviction to federal court — after lawyers took their shots in two other courts.

Judge Alvin Hellerstein suggested Trump’s lawyers had missed their chance by not submitting the US Supreme Court’s ruling on the president’s immunity to a state court judge overseeing the criminal case and, nearly two months later, to a federal judge.

“You made a choice. You tried to take two bites at the apple,” Hellerstein told Trump’s lawyers on Wednesday.

He also questioned Trump’s lawyer’s argument that the case should be taken to federal court because Trump could claim immunity as a defense. Calling the argument “provocative”, he said he would make a decision later.

Trump’s lawyers are trying to move the appeal of his hush money conviction to federal court where judges can interpret challenges to federal preemption and presidential immunity. The removal would also create a faster path for the US Supreme Court to hear the appeal.

Trump was convicted in 2024 of 34 state charges of falsifying business records in connection with hush money payments to adult film star Stormi Daniels.

During oral arguments on Wednesday, Hellerstein said Trump’s lawyers appeared to have made a strategic decision to bring the Supreme Court’s decision on the president’s immunity first to presiding state Judge Juan Merchan, before trying to take the case to federal court, which came 58 days after the ruling.

Trump lawyer Jeffrey Wall pushed back against Hellerstein’s comments that he was trying to take another bite at the apple.

Judge Merchan said “it would have been an insult to the dog” if they had bypassed him, Wall said. He said they had to move immediately before a state judge because Trump was scheduled to sentence him 10 days later.

Hellerstein said Trump’s lawyers missed the 30-day window allowed under the law to move the case to federal court and that they had the burden of whether there was “good cause” to allow them to try again.

“All you’ve done is your good cause is that you’re afraid to upset the state courts and you want to give the state courts the first chance” to rule on the Supreme Court’s decision before arguing it in federal court, the judge said.

“You’ve made a strategic decision. You’re looking at where you can get a better decision and that’s indicative of intent,” the judge said.

“My thesis was that it was fatal to you,” Hellerstein said.

Trump is simultaneously appealing his conviction in state court on 34 counts of trading records that influenced the 2016 presidential election. That appeal could ultimately be brought to the U.S. Supreme Court, but it has additional layers of review.

Hellerstein previously rejected Trump’s attempt to move the case to federal court, finding the argument that Trump’s presidential immunity did not apply. Trump later tried again after the Supreme Court ruled on presidential immunity. He argued that evidence, including the testimony of former Trump White House adviser Hope Hicks and her tweets while in office, was improperly used and her conviction should be overturned.

At the time, Hellerstein rejected the removal proposal, writing, “Private plans with private actors, unrelated to any statutory or constitutional authority or executive function, are considered informal acts.”

Trump appealed, and in November the Second Circuit Court of Appeals sent Hellerstein back for further analysis, taking into account the Supreme Court’s decision on presidential immunity.

On Wednesday, Wall, a lawyer for Trump, argued that when the Manhattan district attorney’s office turned over evidence they argued were official acts — such as Trump’s tweets, the trial testimony of his former White House aide Hope Hicks, and testimony about Trump’s conversations with his attorney general — it changed the case and should now be moved to federal court.

“The district attorney had those keys in his hands. He didn’t have to introduce that evidence at trial to prove his case. Once he did that, the prosecution related to those official acts,” Wall argued.

“Is that enough to make a federal case? I think the answer is clearly yes,” Wall said.

The lawyer added, “I don’t think you should get to the bottom of it. That’s all for the Second Circuit.”

Wall said the judge doesn’t have to decide the merits of the defense’s arguments, only that they have what he calls a “colorable defense” to move the case to federal court.

Steven Wu, an attorney with the district attorney’s office, argued that fighting for evidence is not a defense to criminal charges.

“The defendant seems to assume that because evidence of official acts is presented that somehow changes the nature of the criminal act. That is not true. The charges arise from conduct that is completely informal and private,” Wu said.

During Wednesday’s argument, while the judge was skeptical of many of Trump’s legal arguments, he acknowledged a technical trick that appealed to him.

“It’s a delicious idea because I threw the whole issue up to the appeals court,” Hellerstein said.

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