Anti-Skadden Protester’s Suit Spotlights Free Speech Gray Area

An ex-prosecutor who says he was arrested while protesting Skadden’s $100 million deal with President Donald Trump is now fighting to establish free speech rights at privately owned public spaces.

David O’Keefe, a retired Manhattan assistant district attorney, says Brookfield Properties and NYPD officers violated his First Amendment protections when he was arrested at the privately owned public space outside Skadden’s New York City office.

His suit challenging the arrest is reviving questions about the power to picket at so-called “POPS” that were fought over—but not quite settled—during the “Occupy Wall Street” protests.

“The courts have not resolved what the status of these spaces is and what kind of expressive rights we have in them,” said Thomas Healy, a First Amendment professor at Seton Hall Law. “I think this case will force them to.”

‘I Found Your Spine’

New York City has a long list of parks and plazas owned by corporations rather than the government. According to the city website, it has 590 “areas dedicated for public use and enjoyment, owned and maintained by private property owners in exchange for bonus floor area or zoning waivers.”

David O’Keefe at the “Rule of Law” rally in Manhattan on May 1, 2025.

Photographer: Mike Vilensky/Bloomberg Law

O’Keefe filed his lawsuit in the US District Court for the Southern District of New York on Dec. 18 against Brookfield, the owner of the privately owned public space that abuts Skadden’s headquarters in Manhattan. The POPS’ security provider, Allied, the NYPD officers, and the City of New York are also defendants.

Like a smattering of other lawyers, he’s speaking out against firms that struck deals with Trump earlier this year to avoid punitive executive orders targeting their firms, including Skadden.

Skadden, which isn’t a defendant in the suit, didn’t respond to a request for comment on O’Keefe’s protest or if it had a position on whether he can stage it outside the firm’s office.

O’Keefe says he was unlawfully arrested after refusing to leave the area outside the firm’s office during a one-man protest he staged there, holding a sign reading “Hey Skadden I Found Your Spine In The Trash Lying Next To Your Values!”

“I’m standing there with the sign saying, ‘Skadden, you’re a coward,’” he recalled in an interview with Bloomberg Law. “I thought, ‘I could move 40 feet and avoid being arrested, but what a hypocrite I would be.’”

He was charged with trespassing, but the charge was later dropped, he said.

Brookfield, the NYPD, and Allied declined to comment. A spokesman for the City Law Department said: “We will review the complaint and respond in the litigation.”

Uphill Climb

A court battle over protests in such spaces came amid the Occupy Wall Street demonstrations in 2011, when protesters challenged their removal from lower Manhattan’s Zuccotti Park, another Brookfield-owned public space. A New York State court allowed the city to remove the protesters, saying that even if they did have First Amendment rights there, that wouldn’t allow them to camp out in the park.

That decision left the issue in a gray area, said Michael Linhorst, an attorney for the Cornell Law School First Amendment clinic representing O’Keefe. “We think it’s important for New Yorkers to have case law that clearly states you have the same rights in these spaces as you do in any other public space.”

But the case could be an “uphill battle,” said Mary Anne Franks, a George Washington University Law School professor. For the First Amendment to apply to private actors, “the private owner must be so intertwined with the government that it can be considered part of the government,” she said. “It is not clear based on the facts in the complaint” that the space in question meets that standard, she said.

Healy, at Seton Hall, said O’Keefe has persuasive arguments. Barring protests at POPS would allow the city to avoid constitutional constraints by outsourcing public space development to private developers, he said.

For Big Law, the lawsuit offers another reminder of a tumultuous chapter.

“Here is a picture of a lawyer alone with a sign on an issue of public concern,” said Norman Siegel, the former head of the New York Civil Liberties Union. “An issue that, interestingly enough, affects the legal community. It’s a quintessential peaceful protest. So the fact pattern is very good.”