It is a Monday afternoon in August, and midtown is as empty as it gets all year. But Randy Mastro, the lawyer who has made himself a sharp thorn in Mayor Zohran Mamdani’s side, is in his 27th-floor office near Bryant Park. His wife and dog are on vacation, but Mastro couldn’t be busier, and he couldn’t be happier. “The only place I’m going this month,” he says with an enthusiastic growl, “is the courthouse on Staten Island.”

The source of his good mood and overflowing schedule is the spate of lawsuits Mastro has filed against the City of New York and the mayor. The most recent, and the most prominent, is Mastro’s attempt to halt the rollout of a new pied-à-terre tax on second homes worth $5 million or more and co-ops and condos valued above $1 million of which the owner isn’t the primary resident. Mastro won the first legal round when a Staten Island judge issued a temporary restraining order earlier this month, stopping the notices about the possible surcharge. Perhaps more important for Mastro, he appears to have gotten under Mamdani’s skin. “There are few things more certain in New York City than death, taxes, and Randy Mastro filing a lawsuit against this administration,” the mayor quipped in a press conference in what seemed to be an attempt to belittle Mastro as a gadfly.

Mastro, however, is no mere annoyance. His fluffy head of white hair and matching beard may give him the appearance of a cuddly uncle, but on his desk is a bottle opener shaped like a hammer and engraved YOU’RE RANDY FUCKIN’ MASTRO, a parting gift from a colleague at a former firm. During his time as a top aide under Mayor Rudy Giuliani, Mastro’s muscular wrangling over everything from city budgets to taxi regulations provoked the Daily News to call him, in 1998, “the only trigger man in town who can make Giuliani look like Mr. Nice Guy.”

Mastro has been working in and around the highest levels of city government for four decades, and he knows which legal and political buttons to push, when to turn on the charm, and when to throw punches to get what he wants. In 1985, hired by then–U.S. Attorney Giuliani as a prosecutor in the Southern District, Mastro........

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