James Dolan's Big Risk

The Madison Square Garden owner tempts a political class growing sick of him

There aren’t too many public figures, at least locally, more detestable than James Dolan, the scion of the Cablevision empire and the owner of the Knicks, Rangers, Madison Square Garden, Radio City Musical Hall, and the Beacon Theatre. For years, his tantrums have belonged to the background noise of the city, common enough to be mostly tuned out, like another mediocre Knicks season. Fans can cry sell the team all they want and good government types can wail about the full property tax break Madison Square Garden enjoys, worth $43 million a year. Over 40 years, since the Garden was first exempted in 1982, that comes out to more than $875 million. Never—until now, perhaps—has such a gift been threatened.

Dolan now enters uncharted territory. For decades, the New York political class has been mostly content to take his family’s donations and shut up. Those with power, in particular, either tolerated him or allowed him to have his way, never daring to upset his fiefdom. For 21 years, the speaker of the State Assembly was a man named Sheldon Silver who, for long stretches of his tenure, was the most dominant Democrat in the state. Silver, a Manhattan Democrat, had a near-dictatorial hold on the Assembly. He also happened to be a die-hard Rangers fan, the sort of pol who could be seen frequently at the Garden. No bill to repeal the property tax abatement was making it through Silver’s Assembly. The greatest favor the speaker, who would eventually be indicted on corruption charges and forced from his perch in 2015, would perform for Dolan was not preserving his tax break, though; it was almost single-handedly killing plans for a new stadium on the West Side of Manhattan that would have housed the New York Jets and a possible future Olympics. Seen as a direct competitor to Madison Square Garden, the West Side Stadium was a top priority for Michael Bloomberg, the billionaire mayor. Silver did not care. Dolan won.

In the 2010s, Silver was eclipsed by Andrew Cuomo, the imperial Democratic governor who served for more than a decade until his own resignation in disgrace in 2021. Dolan formed a tight bond with Cuomo, built on their love of Billy Joel and Dolan’s lavish donations to the governor’s various re-election campaigns. In the depths of Covid, Dolan sat on Cuomo’s advisory board for re-opening the city. Silver’s fall and the eventual takeover of the State Senate by progressive Democrats—Dolan-friendly Republicans had run the upper chamber until 2019—couldn’t matter much to the billionaire owner if he had Cuomo.

Much has now changed.