NYC Deputy Mayor Won’t Work for a Socialist: New York Brief

Sept. 11, 2025, 11:01 AM UTC

New York City First Deputy Mayor and ex-Big Law litigator Randy Mastro has worked for everyone from Eric Adams to Rudy Giuliani to James Dolan.

But he’d draw the line somewhere. “I will never work for a socialist,” Mastro told me in two wide-ranging interviews.

One year after having to withdraw his nomination to lead the city’s law department amid pushback, Mastro is one of the most influential attorneys in New York City Hall.

“It feels like he’s running stuff right now, because the mayor has so many other issues,” said longtime Manhattan councilwoman Gale Brewer.

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And he’s well aware the next six months could be his last in city government. With his boss behind in polls to self-described Democratic Socialist Zohran Mamdani, Mastro said he’s “treating every day like it is precious.”

Mastro joined the Adams administration in March. He traded in the trappings of Big Law at King & Spalding for a ground-floor City Hall office where he brings his dog to work and doesn’t have—or want—a computer. (He uses an iPhone with an attached keyboard.)

“Certainly leaving a major law firm partnership to come into city government involves a very significant financial sacrifice,” he said. “But there’s dignity in public service. It’s a calling.”

In that calling, he’s led negotiations on the city budget; opened a pro-bono civil legal services office; and helped the mayor stake out centrist ground on immigration.

He signed the order to open an ICE office at Rikers that was recently struck down in court. “We stand up for New York when the federal administration is doing something that’s contrary to New York City’s interests,” he said. “That’s why we’ve gone to court now in two dozen cases challenging the Trump administration or supporting cases challenging the Trump administration.”

But, “We said we would cooperate with federal law enforcement officials in going after violent transnational criminal gangs. That’s good for our city.”

As for what’s next, Mastro misses the courtroom. His style as an attorney was once likened to “wrestling an alligator,” and he still keeps a rubber alligator figure in his office. “The law is my first love, and I expect to go back to practicing,” he said.

More from our chat, below:

On the city’s finances, after Comptroller Thomas DiNapoli said New York City may be headed for a $13 billion deficit: “We are a balanced budget now. It’s prudent to be conservative in your projections of revenue, but in each recent year, revenue has actually been higher than projected. That’s not to say there’s not reason to be concerned about some of the things going on in Washington and ways the federal administration is cutting back on certain programs and reducing funding for others, but we are taking those things into account and have budgeted reserves.”

On a judge’s finding that the order he signed to open an ICE office on Rikers was illegal: “Their case was based on a hyper-technical, alleged conflict of interest, that amounted to claiming falsely that the mayor had a conflict, but that he couldn’t delegate to me, or apparently anyone else in this administration, the authority to make the decision whether to allow that cooperation with federal law enforcement. So effectively, the judge, by buying into that bogus argument, ruled that the administration couldn’t make that decision at all, even though, legally, the city administration has the right to cooperate with federal law enforcement on criminal matters under local law. So that’s why you have appellate courts, because trial judges get it wrong.”

On still representing Madison Square Garden in Charles Oakley’s ongoing case over removal from a Knicks game: “Madison Square Garden and James Dolan stand up for their principles. They have strong convictions, and they stand up for their convictions, and they support their lawyers.”

Sanctuary City Dismissal Request

New York City will move to dismiss the Trump administration’s lawsuit seeking to strike down the city’s “sanctuary city” measures, my colleague Beth Wang reports.

DOJ’s suit over the laws—which limit federal and city cooperation on immigration enforcement—“fails to plausibly allege that federal law preempts” the city’s laws, according to a pre-motion letter Wednesday. Federal immigration law gives the city the option to help with enforcement but doesn’t require it, the letter says.

The Justice Department in July filed suit against New York City in Brooklyn federal court, saying the city’s immigration policies are unconstitutional and make it harder for immigration officers to do their jobs. DOJ has filed similar suits against Boston, Rochester, and four New Jersey cities.

New York City cited a July federal district court ruling that dismissed a similar suit against Illinois and Chicago. The judge in that case said the policies at issue are delegated by the US Constitution for local governments.

They Said It

“The city of New York, as powerful and mighty as it is, is still a subdivision of the state, so any tax increase has to come across my desk first. I will work with whomever the mayor is, as long as they want to help foster my policies, which is pro-growth, pro-business.

If it’s Mamdani, I will work closely with him to help him understand that when we want to solve society’s problems—and there are many—that we also have to have the resources to do it. That means letting people know we appreciate you being here, you’re building companies, you’re creating wealth. This is your home.”

—Gov. Kathy Hochul to Bloomberg TV on Wednesday. Read more of her thoughts on Mamdani, taxes, nuclear power, AI, and a looming LIRR strike, or watch the full interview here

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To contact the reporter on this story: Mike Vilensky at mvilensky@bloombergindustry.com

To contact the editor responsible for this story: Tina Davis at tdavis@bloombergindustry.com

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