A federal judge was skeptical of President Donald Trump’s argument to try to appeal his hush money conviction to federal court — after lawyers have already taken their shot in two other courts.
Judge Alvin Hellerstein suggested that Trump’s lawyers missed their chance by first taking the US Supreme Court’s ruling on presidential immunity to the state court judge who oversaw the criminal trial and not to a federal judge until nearly two months later.
“I made a choice. You look for two bites at the apple,” Hellerstein told Trump’s lawyers Wednesday.
He also quizzed Trump’s lawyer on the argument that the case should go to federal court because Trump can claim immunity as a defense. Calling the arguments “provocative,” he said he would issue a ruling later.
Trump’s lawyers are trying to get the appeal of his hush money conviction moved to federal court where judges can interpret challenges involving federal preemption and presidential immunity. Removal would also be a faster path for the appeal to be heard by the US Supreme Court.
Trump was convicted in 2024 of 34 state counts of falsifying business records in connection with hush money payments to adult film star Stormy Daniels.
During oral arguments on Wednesday, Hellerstein said Trump’s lawyers appeared to have made a strategic decision to bring the Supreme Court’s ruling on presidential immunity first to Judge Juan Merchan, the state judge who oversaw the trial, before trying to take the case to federal court 58 days after the decision was made.
Jeffrey Wall, a lawyer for Trump, pushed back against Hellerstein’s comment that he was trying to take another bite at the apple.
“It would have been disrespectful in spades” to Judge Merchan if they had passed him, Wall said. He said they had to move quickly before the state judge because Trump would be sentenced by him 10 days later.
Hellerstein said Trump’s lawyers missed the 30-day window allowed under the statute to move the case to federal court and their burden now was whether there was “good cause” to allow them to try again.
“All you have to do is say your good cause is that you’re afraid of angering the state court and you want to give the state court the first chance” to rule on the Supreme Court decision before trying the argument in federal court, the judge said.
“You made a strategic decision. You are seeing where you can get a better decision and this is indicative of the intention,” said the judge.
“My thesis is that it was fatal to you,” Hellerstein said.
Trump is simultaneously appealing his conviction on 34 counts of falsifying business records to influence the 2016 presidential election in state court. That appeal could ultimately go to the US Supreme Court but has additional layers of review.
Hellerstein had previously rejected Trump’s effort to bring the case to federal court, finding that the argument that Trump had presidential immunity did not apply. Trump later tried again after the Supreme Court’s ruling on presidential immunity. He argued that the use of evidence, including testimony from former Trump White House adviser Hope Hicks and his tweets while in office, were improperly used and his conviction should be overturned.
At the time Hellerstein denied that motion for removal, writing, “Private schemes with private actors, not connected to any statutory or constitutional authority or function of the executive, are considered unofficial acts.”
Trump appealed and in November the Second Circuit Court of Appeals sent Hellerstein back to conduct further analysis considering the Supreme Court’s ruling on presidential immunity.
On Wednesday, Wall, Trump’s lawyer, argued that when the Manhattan district attorney’s office introduced evidence of what they argued were official acts — such as Trump’s tweets, trial testimony from his former White House aide Hope Hicks, and testimony about conversations Trump had with his attorney general — it changed the case and should now be brought to federal court.
“The district attorney held those keys in his hand. He didn’t have to introduce that evidence at trial to prove his case. Once he did it became a prosecution related to those official acts,” Wall argued.
“Is that enough to make it a federal case? I think the answer to that is obviously yes,” Wall said.
The attorney added, “I don’t think you should get to the bottom of that. It’s all for the Second Circuit.”
Wall said the judge doesn’t have to decide the merits of the immunity argument, only that they have what’s called a “colorable defense” to take the case to federal court.
Steven Wu, an attorney for the district attorney’s office, argued that a fight over evidence is not a defense to criminal charges.
“The accused seems to assume that because evidence of official acts is introduced that it somehow transforms the nature of the criminal action. That is not true. The charges result from conduct that is completely unofficial and private,” said Wu.
During Wednesday’s argument, while the judge was skeptical of many of Trump’s legal arguments, he acknowledged a technical maneuver that appealed to him.
“That’s a delicious thought because then it brings the whole problem down to the Court of Appeals,” Hellerstein said.
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