A federal judge tangled with an attorney for President Donald Trump on Wednesday and appeared skeptical of his arguments in a bid to erase Trump’s 2024 hush-money conviction.
Trump’s personal attorneys at the time, Todd Blanche and Emil Bove, made a strategic and fatal mistake in July 2024 by going to the trial judge for relief in the hush-money case following the U.S. Supreme Court’s ruling giving Trump immunity rather than going directly to federal court, Judge Alvin Hellerstein said at a hearing that lasted more than three hours in U.S. District Court in lower Manhattan.
“You made your choice and sought two bites of the apple; you should have gone to federal court first,” Hellerstein said at the hearing as Trump tries for a third time to move the case to federal court in an effort to overturn 34 guilty counts.
Jeffrey Wall, a former principal deputy U.S. solicitor general who's now representing Trump, argued that Trump was entitled to a federal forum and that had his attorneys at the time run to federal court first, they would have been acting prematurely without having given trial Judge Juan Merchan a chance to look at it.
Hellerstein rejected that argument, saying Wall was beating a dead horse. Hellerstein said nothing was stopping Trump’s attorneys from coming first to federal court to make their case.
Steven Wu, representing Manhattan District Attorney Alvin Bragg, also argued that Trump could have gone to federal court first but made a strategic decision to go to state court first.
Wu said Trump cannot have it both ways.
“You cannot go to state court and when you are unhappy with that result go to federal court,” he said.
Hellerstein said that the arguments were provocative and that he would issue his decision soon.
A New York jury found Trump guilty in May 2024 on all 34 felony counts of falsifying business records to conceal a $130,000 hush-money payment to adult film star Stormy Daniels, making him the first president convicted of a crime. Ten days before Trump was sworn in for a second term as president, Merchan sentenced him to an unconditional discharge, meaning the conviction stands but with no further penalties, such as jail time.

The 2nd U.S. Circuit Court of Appeals ordered Hellerstein in November to reconsider his decision to keep the case in state court rather than move it to federal court, where Trump could seek to have it thrown out on presidential immunity grounds.
A three-judge panel ruled that Hellerstein mistakenly failed to consider “important issues relevant” to Trump’s request to move the case to federal court. They said they “express no view” on how he should rule.
Trump did not attend Wednesday’s hearing, which followed lengthy written submissions filed by his attorneys, as well as prosecutors from the Manhattan district attorney’s office, which is fighting to keep the case in state court.
Hellerstein, appointed by President Bill Clinton, has twice denied Trump’s efforts to move the case to federal court. The first effort was after Trump’s March 2023 indictment, and the second followed his May 2024 conviction and the Supreme Court ruling that presidents and former presidents cannot be prosecuted for official acts.
In his second decision denying Trump's request, Hellerstein said that his lawyers had failed to meet the high burden of proof for changing jurisdiction and that his conviction for falsifying business records involved his personal life, not official actions that the Supreme Court ruled are immune from prosecution.
The 2nd Circuit panel said Hellerstein’s ruling “did not consider whether certain evidence admitted during the state court trial relates to immunized official acts, or, if so, whether evidentiary immunity transformed” the hush-money case into one that relates to official acts.

