Veteran New York litigator Randy Mastro has initiated a series of legal challenges against Mayor Mamdani's administration, filing five lawsuits and indicating potential for more. Mastro's legal actions target the rollout of the city's pied-à-terre tax and the mayor's plan to freeze rents on stabilized apartments.

Mastro claims the pied-à-terre tax, which applies to second homes valued over $5 million and condos over $1 million where the owner is not a primary resident, is illegal due to its placement of the burden of proof on homeowners to demonstrate they do not owe the tax. He stated, "That's not how the tax system is supposed to work." The administration has also reportedly sent notices to individuals who reside in the city as primary residents and publicly disclosed their names, according to Mastro.

Mastro is also contesting the administration's rent freeze policy. He argues that under the City Charter, an independent Rent Guidelines Board is mandated to make such decisions. Mastro alleges that Mayor Mamdani stacked the board with his appointees, thereby rigging the system against landlords and preventing a true examination of landlords' costs and the potential for apartments to remain vacant.

Mastro, a former federal prosecutor and deputy mayor under Rudy Giuliani, has a long history of legal battles. He has previously represented clients in high-profile cases, including defending former New Jersey Governor Chris Christie in the "Bridgegate" scandal. He also previously worked for Mayor Eric Adams.

Mayor Mamdani, a former assemblyman who won the mayoral election on a platform advocating for significant policy changes, has acknowledged Mastro's legal activity, quipping, "There are few things more certain in New York City than death, taxes and Randy Mastro filing a lawsuit against this administration."

Mastro, described by a former colleague as an "excellent litigator" who is unconcerned with the power of his opponents, has a track record of success in legal contests, including a recent case that prevented the construction of subsidized housing in lower Manhattan. His current legal challenges position him as a prominent antagonist to Mayor Mamdani's policies.