Lawyers who have practiced before the Clinton appointee say he’s known to operate a bit differently.

U.S. District Court Judge Alvin K. Hellerstein, in Manhattan, Sept. 2, 2016. | Todd Heisler/The New York Times via Redux
“He tries very hard to do the right thing. [He] just has his own sense of what that is,” one former federal prosecutor said.
“He’s just old and old-school and does things his own way and doesn’t give a shit what anyone thinks about him,” said another former federal prosecutor, who — like most lawyers interviewed for this story — was granted anonymity to speak candidly about a judge they may appear before in the future.
Hellerstein has ruled against President Donald Trump or his administration in other high-profile cases, including the charges involving alleged hush money payments to pornstar Stormy Daniels. Hellerstein twice rejected Trump’s bids to move the case to federal court.
Just two months ago, an appeals court overturned one of those rulings.
Hellerstein also issued a sweeping order last May blocking the Trump administration from deporting immigrants under the Alien Enemies Act with little, if any, due process. The ruling essentially halted such deportations in the Southern District of New York, where the judge sits.
While Hellerstein’s age is certain to raise eyebrows, lawyers interviewed for this story raised no doubts about his fitness. However, some said he has long exhibited an independence bordering on stubbornness.