‘You sought two bites at the apple’

A federal judge casts doubt on the President ‘Donald Trump’His argument is to move his appeal of the hush money conviction to federal court, after lawyers tried their luck in two other courts.

Judge Alvin Hellerstein argued that Trump’s lawyers missed their chance by first appealing the U.S. Supreme Court’s presidential immunity ruling to the state court judge overseeing the criminal case, rather than to a federal judge until almost two months later.

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

He also grilled Trump’s lawyer about his argument that the case should be moved to federal court because Trump could claim immunity as his defense. Calling the arguments “provocative,” he said he would issue a ruling later.

Trump’s lawyers are trying to move the challenge of his hush money conviction to federal court, where judges could interpret challenges related to federal preemption and presidential immunity. The repeal would also open a faster path for appeals to be heard by the U.S. Supreme Court.

Trump was convicted in 2024 on 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 lawyers made a strategic decision to first present the Supreme Court’s decision on presidential immunity to Judge Juan Merchan, the state judge overseeing the trial, before trying to move the case to federal court, which he did 58 days after the decision was made.

Trump attorney Jeffrey Wall disputed Hellerstein’s comment that he was trying to take another bite of the apple.

“It would be extremely disrespectful” if they bypassed Judge Merchan, Wall said. He said they needed to appear before the state judge quickly because Trump was scheduled to be sentenced by him in 10 days.

Trump’s lawyers missed the 30-day deadline allowed under the law to move the case to federal court, Hellerstein said, and their responsibility now is whether there’s “good cause” to allow them to try again.

“All you’re doing is saying you’re afraid of angering the state court and you want to give the state court the first chance,” the judge said, granting the Supreme Court ruling before hearing the case in federal court.

“You made a strategic decision. You see where you could have made a better decision, and that shows intent,” the judge said.

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

Trump is also appealing his conviction in state court on 34 charges that he falsified business records to influence the 2016 presidential election. This appeal may ultimately go to the U.S. Supreme Court, but it has additional layers of review.

Hellerstein had previously rejected Trump’s effort to take the case to federal court, finding that Trump’s claim that he had presidential immunity was not valid. Trump was later tried again following the Supreme Court’s presidential immunity ruling. He argued that the use of evidence, including the testimony of Trump’s former White House adviser Hope Hicks and her tweets while in office, was improperly used and his conviction should be overturned.

“Private plans with private actors, unconnected with any legal or constitutional authority or function of the executive branch, are considered unofficial actions,” Hellerstein wrote in denying the impeachment request.

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

Wall, Trump’s attorney, argued on Wednesday that when the Manhattan district attorney’s office presented evidence that they claimed were official actions, including Trump’s tweets, former White House aide Hope Hicks’ trial testimony and testimony about conversations Trump had with his attorney general, it changed the case and should now move to federal court.

“The district attorney held these keys. He did not have to present this evidence at trial to prove his case. When he did that, it became an official proceeding,” Wall said.

“Is that enough to make this a federal case? I think the answer to that is clearly 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 claim, they just have what’s called a “color defense” to move the case to federal court.

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

“The defendant appears to assume that by presenting evidence of official acts, he somehow transforms the nature of the criminal case. This is not true. The charges stem entirely from unofficial and private conduct,” Wu said.

During Wednesday’s argument, the judge was skeptical of many of Trump’s legal arguments, but conceded to a technical maneuver that appealed to him.

“That’s a great thought because I then refer the entire issue to the Court of Appeals,” Hellerstein said.

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