A federal judge has been skeptical of President Donald Trump’s argument to try to send the appeal of his hush money conviction to a federal court — after lawyers have already taken the hit in two other courts.
Judge Alvin Hellerstein suggested Trump’s lawyers missed a chance by first taking the U.S. 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.
“You made a choice. You went for two bites of the apple,” Hellerstein told Trump’s lawyers Wednesday.
He also questioned Trump’s lawyer about the argument that the case should be transferred to federal court because Trump could 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 could rule on challenges involving federal preemption and presidential immunity. Removal would also have a faster path for the appeal to be heard by the US Supreme Court.
Trump was convicted in 2024 of 34 state charges of falsifying business records in connection with hush money payments to adult film star Stormy Daniels.
During oral arguments Wednesday, Hellerstein said Trump’s lawyers appeared to be making a strategic decision to first bring the Supreme Court’s ruling on presidential immunity to Judge Juan Merchan, the state judge who oversaw the trial, before trying to take the case to federal court, which he did 58 days after the ruling.
Jeffrey Wall, a lawyer for Trump, dismissed Hellerstein’s comment that he was trying to bite the bullet.
“It would have been disrespectful” to Judge Merchan if he had bypassed him, Wall said. He said he needed to move quickly before the state judge because Trump was to be sentenced by him 10 days later.
Hellerstein said Trump’s lawyers missed the 30-day window allowed by statute to move the case to federal court, and that their task now is whether there is “good cause” to allow them to try again.
“All you’re doing is saying your good cause is that you’re afraid of upsetting 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 see where you can get a better decision and that indicates intent,” the judge said.
“My thesis is that it was fatal to you,” Hellerstein said.
At the same time, Trump is appealing his conviction on 34 counts of falsifying business records to influence the 2016 presidential election in state court. The appeal may ultimately go to the US Supreme Court, but it has additional layers of scrutiny.
Hellerstein previously rejected Trump’s effort to move the case to federal court, arguing 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 the testimony of former Trump White House adviser Hope Hicks and his tweets while in office, was improperly used and his conviction should be overturned.
At the time, Hellerstein denied that motion to dismiss, writing, “Private schemes with private actors, unrelated to any statutory or constitutional executive authority or function, are considered unofficial acts.”
Trump appealed, and in November the Second Circuit Court of Appeals sent it back to Hellerstein for further review, taking into account 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 said were official documents — such as Trump’s tweets, testimony from his former White House adviser Hope Hicks and testimony about conversations Trump had with his attorney general — it changed the case and should now be moved to federal court.
“The district attorney held those keys. 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 records,” Wall argued.
“Is that enough to become a federal case? I think the answer to that is obviously yes,” Wall said.
The lawyer added: “I don’t think you need to get to the bottom of this. It’s all for the Second Circuit.”
Wall said the judge doesn’t have to decide the merits of the immunity argument, just that they have what’s called a “colorable defense” to move the case to federal court.
Steven Wu, a lawyer for the district attorney’s office, argued that a fight for evidence is not a defense to criminal charges.
“The defendant seems to assume that because evidence of official acts is introduced, that somehow transforms the nature of the criminal action. That is not true. The charges arise out of conduct that is completely unofficial and private,” Wu said.
During Wednesday’s argument, while the judge was skeptical of many of Trump’s legal arguments, he acknowledged one technical maneuver that appealed to him.
“It’s a delicious thought because then they throw the whole thing on the Court of Appeals,” Hellerstein said.
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