Bruce Blakeman, the Republican nominee for New York governor, promised last November to erect a wall of spy gear, license plate readers, and biometric surveillance between the city and the suburbs. He has since received millions of dollars in donations from the family and businesses of James Dolan, the owner of Madison Square Garden, where a network of cameras capture the faces of (nearly) every patron who walks in the arena and corporate security forces hunt for critics of the boss.

Dolan’s support of Blakeman, the executive of suburban Nassau County, could be seen as something of a counterintuitive move in a state long run by Democrats, and in a year when political surveys are picking up indications of a blue wave. He’s down by nine points or more in most polls.

Blakeman, however, backs data centers, AI deepfakes, Flock surveillance, ICE, private militias, and president Donald Trump. All of which makes him at least somewhat simpatico with Dolan, the Trump-allied magnate operating the sports world’s best-known surveillance state. Dolan has long been a mercurial presence in the political game, and in fact, as Politico notes, he supported Blakeman’s opponent, Governor Kathy Hochul, during the last election. Dolan’s sheer amount of spending in the race could also benefit him, even if his preferred candidate loses.

Long an outsized force in sports and entertainment, Dolan now has a chance at a major political role, too.

“Dolan can step into the breach and become the biggest player in [New York’s] Republican politics, donor-wise, and I'm sure his people are smart enough to know that,” one veteran strategist tells WIRED.

James Dolan has given heavily before, including nearly a million dollars to Trump’s reelection campaign and the Republican National Committee in the 2020 election cycle. But the New York governor’s race represents another level, a review of city, state, and federal databases shows.

The Dolan family has given $108,000 to Blakeman’s campaign directly and another $970,000 to the local Nassau County Republican party, which in turn has become Blakeman’s single-largest contributor. But that’s just for starters. MSG entities have contributed another $2 million to a political action committee supporting Blakeman’s run. That super PAC, Strong and Safe New York Inc., which lists Madison Square Garden’s top government relations executive as an officer, has raised $5.3 million overall.

That helped make up for a 9-to-1 cash advantage that the governor’s campaign reported over her challenger’s at the last filing deadline in July.

Dolan and MSG’s bankrolling of Blakeman could come with risks, however. Opposition to Dolan’s use of facial recognition has hit a new peak locally, where a majority of the City Council are now in favor of a bill to rein in biometric surveillance. State lawmakers introduced a bill to end the property tax break that has been worth over a billion dollars to Madison Square Garden. The federal government has agreed to take over the $8 billion renovation of the train station below Madison Square Garden—a project that could pay Dolan’s company $500 million or more. But multiple sources note that state and local authorities will likely continue to have a say.

Meanwhile, the New York attorney general’s investigation into MSG’s deployment of facial recognition continues to progress, a source familiar with the matter tells WIRED. And while mayor Zohran Mamdani’s critiques of Dolan’s security practices have been muted, so far, there are signs that may be changing. One of his commissioners said last month that “this kind of mass surveillance opens the door to abuse and discrimination.”

Dolan’s friction with state and local officials is coming at what should be a peak moment for the mogul: the long-suffering basketball team he owns, the New York Knicks, recently won their first title in 53 years. And yet, during the Knicks’ run in the NBA Finals, his organization fought with the mayor and the police commissioner over security procedures around the Garden. In the days leading up to the championship parade down Broadway, a source with knowledge of the preparations tells WIRED, Dolan’s team tussled with the governor’s and the mayor’s for control over the event, particularly over who got to be on stage and in the audience as the players were presented with keys to the city at City Hall.

“Dolan micromanaged the Knicks parade like it was his own sweet sixteen,” the source tells WIRED.

Dolan and Blakeman, on the other hand, have in recent years demonstrated a host of common interests, common enemies, and one extremely prominent mutual friend. In June, Trump came to the Garden for game three of the Finals; Blakeman joined the president of the United States and the team’s owner in the luxury box. Two months later, in mid-August, Strong and Safe New York released an ad calling on Hochul to stop blaming the state’s problems on Trump. (Strong and Safe, which is also supporting James’ opponent in the attorney general’s race this year, recently sent $83,400 to her former employers, the Republican law firm behind Kanye West’s presidential bid in 2020.)

Blakeman has been one of the state’s most enthusiastic implementers of Trump’s mass deportation machine, ordering local detectives to work with ICE and opening up the county’s jails for those caught up in the crackdown. (Less than 5 percent of the immigrants jailed had violent criminal records, a Newsday investigation found.)

He recruited dozens of armed “special deputies,” which looked a whole lot like a personal militia to critics. And when Mamdani won his New York mayoral election last November, Blakeman promised to erect a wall of surveillance along the city line to keep suburban residents safe. “We are installing technology along the border of New York City that will read license plates, that will have facial recognition, that will have video cameras,” he told Fox News.

Since then, drivers in Nassau County have become some of the most surveilled in the nation, with a Flock Safety camera for every 9.5 miles of road, according to the DeFlock activist group.

Dolan has been aggressive in his deployment of surveillance at his venues, which include the Sphere in Las Vegas and Radio City Music Hall in Manhattan. Arrays of surveillance security cameras tied to a video management system running a facial recognition program are a major reason why MSG “is the most secure venue in the country,” Dolan has previously said.

“They’re in the same mindset that surveillance is good for business,” Brad Hoylman-Sigal, the Manhattan borough president, says of Blakeman and Dolan. “And I don’t know how that's a winning political issue.”For the majority of more than three decades in politics, Blakeman presented himself as a moderate as he launched unsuccessful bids for state comptroller, US House and Senate seats, and even New York City mayor.

Then in 2021, Blakeman went full MAGA, and won his Nassau County Executive race by 2,000 votes. He’s been tied to Trump and the Trumpists ever since, starting with an all-out push behind MAGA megadonor Miriam Adelson’s multibillion plan to build a casino on the site of the Nassau Coliseum. The bid was ultimately withdrawn.

Hochul’s recent political journey has gone in something like the opposite direction. Once considered a conservative Democrat, she’s become a vocal Trump critic; passed a law banning local cops from cooperating with ICE (a move Blakeman said was “written with the blood of the victims of illegal migrants,” before reluctantly complying with it; and put in place the country’s first statewide data center moratorium (Blakeman called that “crazy,” while using AI to lampoon Hochul in his TV spots).

Dolan largely stayed out of last year’s mayor’s race. But an MSG political action committee, the Coalition to Restore New York, dumped more than $400,000 into 11 local City Council races. Seven of them won, and all but one lined up to support Julie Menin as City Council president, who was seen as a check on Mamdani’s power.

Menin now holds the power to bring the Council’s bill curbing facial recognition to a vote—or to let it die without one. Menin, who returned a Dolan donation in 2023, is currently undecided on how to proceed, the veteran strategist tells me. “She doesn't want to ban facial recognition”—and to be clear, the bill in the Council doesn’t aim to do that. “She thinks that it should be reformed, and that there should be guardrails and parameters,” the strategist says. (A Menin spokesperson did not reply to a request for comment.) One longtime outside counsel for MSG has filed a flurry of lawsuits against the Mamdani administration, while a second former outside attorney has raised a million dollars for a political organization to counter the mayor’s agenda.

John Catsimatidis, a billionaire Republican donor, indicated to Politico that Dolan’s backing of Blakeman could be seen as a move against Mamdani, of sorts.

“Everybody believes the governor has oversight of the mayor,” he said. (Representatives for both the Hochul and Blakeman campaigns did not respond to requests to comment for this story. Neither did a City Hall spokesperson. But Mamdani did say on Monday that a candidate "who embraces ICE and has gone so far as to create, effectively, a private militia in Nassau County” is “in many ways the antithesis” of what New Yorkers want.)

The governor is not without her own well-funded allies, however. That includes Blakeman’s ex-wife Nancy Shevell, who’s now married to Paul McCartney. She donated $18,000 to Hochul. The Pegula family, which owns the NFL’s Buffalo Bills, has given her and the state Democratic Party nearly $175,000. (A small sum to pay, considering Hochul helped steer $600 million in state money into her hometown team’s new stadium.) Uber spent more than $12 million in a six-month period to a PAC supporting Hochul, who has proposed auto insurance reforms that the ride-share giant likes.

That’s way more than Dolan has devoted to his candidate so far. But what he has given appears to be the most money a Dolan-backed business has devoted to a political cause since it spent an estimated $30 million in 2004 to stop a football stadium from being built on Manhattan’s west side, a signature project by the mayor at the time, Michael Bloomberg. Dolan’s push was so effective, it caused the mayor to sputter in public. “You’d think,” the mayor fumed on his radio program, that “a company on corporate welfare would be less selfish to the city that has been so good to it.”

For that campaign, Dolan’s firm funded an outfit called the “New York Association for Better Choices,” which took out full-page ads in every city newspaper, ran anti-stadium commercials on local TV, and counted the lobbying firm of a former US senator as one of its many advocates. For this election, Dolan’s chosen candidate is relying heavily on AI. Blakeman’s ads featuring ersatz Hochuls hiding behind dumpsters, getting clowned by Mamdani, and producing BS.

One recent anti-Hochul spot lifted footage from a comedian’s bit—shot in 2011 and criticizing the Republican leader of Wisconsin at the time. “Bruce Blakeman,” the progressive local news outlet Hell Gate proclaimed, “is the governor of slop.”