Retired prosecutor sues New York over arrest while protesting law firm Skadden

By Mike Scarcella

WASHINGTON, Dec 19 (Reuters) - A retired prosecutor has sued New York City and Brookfield Properties in federal court, alleging he was wrongfully arrested while protesting in a public space against law firm Skadden Arps over its deal with President Donald Trump to provide free legal work.

David O’Keefe said in his lawsuit, filed on Thursday, that he was arrested while staging a solo protest in April in a privately-owned but public space outside Skadden’s Manhattan office. He opposed Skadden’s agreement to provide $100 million in pro bono services for Trump-backed initiatives, calling it a threat to the rule of law.

The lawsuit said O’Keefe refused to leave and then was handcuffed, detained for 90 minutes, and charged with trespass. The case was later dismissed. His lawsuit seeks damages and a ruling that U.S. constitutional free speech rights apply in New York’s privately owned public spaces, which private developers create in exchange for zoning benefits.

“O’Keefe’s lawsuit seeks to make clear that the public enjoys the same First Amendment rights in POPS as in any other public space,” his lawyers said in a statement.

Brookfield and the New York City police department did not immediately respond to requests for comment.

Skadden Arps, a prominent firm known for deals and litigation, is not a defendant. The firm did not immediately respond to a request for comment.

Bar records and prior news reports show that O'Keefe was formerly a prosecutor in the Manhattan district attorney's office and led its crime strategies unit. The lawsuit included a photo of O’Keefe at the April protest holding a sign that called Skadden “Trump’s $100 million lap dog.”

Skadden was among nine major law firms that made similar pro bono pledges to Trump after the president began using executive orders to punish law firms over their past legal work, diversity policies and political connections. Skadden and the others have defended the propriety of their White House agreements.

The case is David O’Keefe v. The City of New York et al, U.S. District Court, Southern District of New York, No. 1:25-cv-10532.

For plaintiff: Michael Linhorst and Daniela del Rosario Wertheimer of Cornell Law School First Amendment Clinic, and Gideon Oliver of Gideon Law

For defendants: No appearances yet

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