By Kara Scannell, CNN

(CNN) — A federal judge was skeptical of President Donald Trump’s argument to try to move the appeal of his hush money conviction to federal court — after lawyers already took their shot in two other courts.

Judge Alvin Hellerstein suggested Trump’s attorneys missed their chance by first taking the US Supreme Court’s decision on presidential immunity to the state court judge who oversaw the criminal trial and not to a federal judge until almost two months later.

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

He also quizzed Trump’s lawyer over the argument that the case should move to federal court because Trump could claim as a defense that he has immunity. Calling the arguments “provocative,” he said he would issue a ruling later.

Trump’s attorneys are trying to get the appeal of his hush money conviction moved into federal court where the judges could interpret challenges involving federal preemption and presidential immunity. Removal would also plow a quicker path to have the appeal 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 on Wednesday, Hellerstein said Trump’s attorneys appeared to make a strategic decision to bring the Supreme Court decision on presidential immunity first to Judge Juan Merchan, the state judge who oversaw the trial, before trying to move the case to federal court which it did 58 days after the decision came down.

Jeffrey Wall, an attorney for Trump, pushed back against Hellerstein’s comment that he was trying to get another bite at the apple.

“It would have been disrespectful in spades” to Judge Merchan if they bypassed him, Wall said. He said they had to move quickly before the state judge because Trump was set to be sentenced by him 10 days later.

Hellerstein said Trump’s attorneys missed the 30-day window allowed under the statute to move the case into federal court and their burden now was whether there was “good cause” to allow them to try again.

“All your doing is saying your good cause is you’re afraid to anger 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’ve made a strategic decision. You’re seeing where you can get a better decision and that is indicative of the intent,” the judge said.

“My thesis is that 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 can ultimately be brought to the US Supreme Court but it has additional layers of review.

Hellerstein had previously rejected Trump’s effort to move the case into federal court, finding the argument that Trump had presidential immunity didn’t apply. Trump later tried again after the Supreme Court’s ruling on presidential immunity. He argued the use of evidence, including testimony from Trump’s former White House advisor 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, unconnected 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 it back to Hellerstein to conduct further analysis considering the Supreme Court ruling on presidential immunity.

On Wednesday, Wall, the attorney for Trump, argued 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 now it should be moved into federal court.

“The district attorney held those keys in his hand. He didn’t have to introduce that evidence at trial to prove up his case. Once he did this became a prosecution relating 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 have to get to the bottom of this. It’s all for the Second Circuit.”

Wall said that the judge doesn’t have to decide the merits of the argument on immunity, only that they have what is called a “colorable defense” to move the case into 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 defendant seems to assume that because evidence of official acts is introduced that somehow transforms the nature of the criminal action. That’s just not true. The charges arise out of conduct that is wholly unofficial and private,” Wu said.

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 I then dump the whole problem on the Court of Appeals,” Hellerstein said.

The-CNN-Wire
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