Federal Judge Appears Unconvinced by Trump's Bid to Overturn Hush Money Conviction
A federal judge has signalled strong scepticism toward Donald Trump's latest legal manoeuvre to void his historic hush money conviction, delivering sharp criticism of his legal team's approach during extensive courtroom arguments.
Judge Hellerstein Questions Legal Strategy
Judge Alvin K. Hellerstein, presiding over the matter in Manhattan federal court, displayed evident doubt during nearly three hours of arguments on Wednesday. The judge, tasked by an appeals court to re-evaluate Trump's request to transfer his case from state to federal jurisdiction, repeatedly challenged the former president's lawyer, Jeffrey Wall.
Judge Hellerstein suggested the entire effort might be futile because Trump's legal team waited too long after the May 2024 verdict to seek federal court intervention. He specifically criticised what he described as "taking two bites at the apple" - pursuing remedies in state court before attempting to move to federal jurisdiction.
The Core Legal Battle
Trump was convicted in New York state court in May 2024 on 34 felony counts of falsifying business records. This conviction stemmed from concealing a hush money payment to adult film actor Stormy Daniels, whose allegations of an affair with Trump threatened to disrupt his 2016 presidential campaign.
The former president received an unconditional discharge, meaning his conviction stands but he faced no further punishment. Trump denies Daniels' claim and maintains his innocence, having already appealed the conviction to a state appellate court.
Presidential Immunity Questions
Judge Hellerstein acknowledged that a US Supreme Court ruling, issued approximately a month after the verdict, had introduced unprecedented legal questions. That ruling stipulated that presidents cannot be prosecuted for official acts, creating new legal territory previously unaddressed by the courts.
However, the judge emphasised that the high court's decision made clear that "a president is not above the law." This balancing act between presidential immunity and accountability forms the crux of the current legal dispute.
Timing and Strategic Decisions
The judge interrupted Wall almost immediately as Wednesday's arguments commenced, telling the lawyer, "I think I have to quarrel with you a bit" regarding the sequence of events following Trump's conviction.
Wall contended that Trump's lawyers faced time constraints after the Supreme Court's 1 July 2024 ruling, as sentencing was scheduled just 10 days later. He suggested that had they attempted to bring the case to federal court at that point, prosecutors might have criticised it as premature.
"Not so," Judge Hellerstein retorted. "That is a decision on your part. You didn't have to do that. You could have come right to the federal court."
Appeals Court Instructions
In November, the 2nd U.S. Circuit Court of Appeals instructed Judge Hellerstein to reconsider his earlier decision that kept the New York case in state court. A three-judge panel found that his September 2025 ruling had failed to consider "important issues relevant" to Trump's request to move the case.
The appeals court specifically noted that Judge 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 concerning official acts.
Prosecution's Position
Steven Wu, a lawyer from the Manhattan district attorney's office, which prosecuted the case and advocates for it to remain in state court, concurred with Judge Hellerstein's assessment. Wu stated that Wall's argument "confirms this was a strategic choice by the defendants."
He added that Trump's lawyers were aware they could have simultaneously submitted arguments to the state court while attempting to transfer the case to federal jurisdiction. Previous rulings, Wu noted, have made it clear that "you cannot go to state court and when you're unhappy, then go to federal court."
Judge's Previous Rulings
Judge Hellerstein, who was nominated by Democratic President Bill Clinton, has twice previously denied Trump's requests to move the case. The first instance was after Trump's March 2023 indictment; the second was the post-verdict ruling that was the subject of Wednesday's hearing.
In that earlier ruling, Judge Hellerstein stated that Trump's lawyers had failed to meet the stringent burden of proof required for changing jurisdiction and that Trump's conviction for falsifying business records pertained to his personal life, not official actions that the Supreme Court has deemed immune from prosecution.
Next Steps and Considerations
The three-judge appeals panel instructed Judge Hellerstein to meticulously review any evidence Trump claims relates to official acts. Should he determine that the prosecution relied on evidence of official acts, the judges advised him to consider several factors:
- Whether Trump can argue those actions were undertaken as part of his White House duties
- Whether Trump "diligently sought" to have the case moved to federal court
- Whether the case can even be transferred to federal court now that Trump has been convicted and sentenced in state court
Judge Hellerstein stated he would issue a ruling at a later date, following what he described as "very provocative arguments" from both legal teams. Trump was not present at Wednesday's proceedings, leaving his legal team to navigate these complex jurisdictional questions that could have significant implications for presidential accountability.
