D
onald Trump has now lost this particular fight three separate times, and it's the same judge delivering the blow each time.
U.S. District Judge Alvin K. Hellerstein, a Clinton appointee sitting in the Southern District of New York, denied Trump's latest bid on Friday to transfer his state hush money case into federal jurisdiction. The stakes were significant. Had Trump succeeded, his lawyers were prepared to argue that his 2024 conviction on 34 felony counts of falsifying business records should be tossed out entirely, shielded by the sweeping presidential immunity doctrine the Supreme Court laid out in July 2024.
Hellerstein wasn't buying it. In his written decision, he called the grounds Trump cited for renewing the request "neither new nor legally sufficient," adding a blunt assessment: "He has failed to show good cause and diligence."
The case traces back to a $130,000 payment made in the final weeks of the 2016 campaign, funneled through Trump's then-lawyer Michael Cohen to adult film actor Stormy Daniels, whose claims of an affair with Trump threatened to derail his run for the White House. Jurors convicted Trump on all 34 counts in May 2024. He was later sentenced to an unconditional discharge, sparing him jail time or a fine so as not to disrupt the start of his second term.
Trump's team has tried repeatedly to get out from under that conviction by arguing it belongs in federal court, not state court, where they believe presidential immunity offers more room to maneuver. This was attempt number three. The first came after his original 2023 indictment. The second followed his conviction and the Supreme Court's landmark immunity ruling. Both were rejected by Hellerstein.
What made this round different is that Trump got a second chance he probably didn't deserve. A three-judge panel on the 2nd U.S. Circuit Court of Appeals ruled last fall that Hellerstein had moved too quickly the second time around, failing to fully examine whether evidence used at trial, including testimony from former aides and social media posts, touched on official presidential acts protected by immunity. So the appeals court sent it back down for another look.
That closer look didn't change anything.
Hellerstein didn't mince words this time either. According to his ruling, there's simply "no statutory basis for removal after verdict, sentencing, and judgment." He went further, dismissing the substance of Trump's core claim outright: "Paying hush money to an adult film star or engaging in a cover-up of an embarrassment are not subsumed in presidential immunity."
The judge also took aim at the timing of Trump's legal strategy. His lawyers, Todd Blanche and Emil Bove at the time, initially sought relief from the state trial judge, Juan Merchan, rather than rushing to federal court after the Supreme Court's immunity decision came down. By the time they pivoted to Hellerstein, nearly two months had passed. That, the judge suggested, wasn't a mistake born of confusion. It was a calculated bet that didn't pay off.
Hellerstein framed it as Trump seeking a "second bite at the apple," something the law generally disfavors. He wrote that the delay reflected a "quintessential strategic decision," and noted pointedly that regretting a strategic choice later doesn't retroactively create good cause to undo it.
Trump attorney Jeffrey Wall had pushed back during arguments, contending prosecutors rushed the case to trial rather than waiting on the Supreme Court, and that Trump's team was working under serious time pressure since his sentencing was scheduled just ten days after the immunity ruling came down. Hellerstein wasn't persuaded.
Trump's team didn't take the loss quietly. A campaign spokesperson called the ruling "baseless and lawless," insisting, somewhat confusingly, that Trump had "already prevailed" at the 2nd Circuit, a reference to last fall's order sending the case back for reconsideration rather than any substantive win. The statement promised a "powerful appeal" and vowed to keep "defeating Democrat weaponization at every turn." Attorney Robert Giuffra Jr. moved fast, filing notice of appeal to the 2nd Circuit almost immediately after Friday's ruling landed.
Manhattan District Attorney Alvin Bragg's office, which brought and won the original prosecution, has consistently argued the case belongs in state court because it centers on personal conduct, not official presidential business. Hellerstein's ruling affirms that reading for a third consecutive time.
The conviction itself isn't going anywhere for now. It remains intact at the state level, and Trump is pursuing a separate appeal through New York's state appellate courts, a track that runs independently of this federal fight.
The hush money case was one of four criminal prosecutions Trump faced heading into the 2024 election cycle. It was the only one that actually went to trial before Bragg's office secured a conviction; the other three were dismissed or otherwise didn't reach a verdict. That distinction has made this case something of a singular legal thread still trailing behind Trump's second term, one that keeps generating headlines even as its practical consequences, an unconditional discharge with no jail time or fine, remain largely symbolic.
Whether the 2nd Circuit gives Trump a fourth shot at this argument is now the open question. Given the panel's history of sending Hellerstein back to reconsider once already, it isn't a foregone conclusion either way.
A federal judge in Manhattan has for the third time rejected President Trump's attempt to move his New York hush money case into federal court, a maneuver his legal team hoped would open the door to overturning his 34-count felony conviction on presidential immunity grounds. U.S. District Judge Alvin Hellerstein ruled Friday that Trump's arguments were "neither new nor legally sufficient" and that he had failed to act with the diligence the law requires. Trump's lawyers have already filed notice of appeal to the 2nd Circuit.
