James L. Dolan has spent nearly 30 years as the owner of the New York Knicks. For much of that time, the team was one of the worst in the National Basketball Association.
After the Knicks went to the championship round of the N.B.A. playoffs in 1999, Mr. Dolan’s first year at the helm, they made the playoffs only seven times over the next 23 years. They had the worst record in the N.B.A. in 2019, prompting the Bloomberg headline “Is the Knicks’ James Dolan the Worst Owner in Professional Sports?”
His reputation in New York City fared about as well, and Mr. Dolan’s actions never seemed to help much. He publicly battled — sometimes in court — the team’s fans, his employees, city politicians and even his own players.
But after a stunning turnaround in the past few seasons, the Knicks have a title within arm’s length. They face off against the San Antonio Spurs in the N.B.A. finals starting Wednesday. If they succeed over the best-of-seven series, Mr. Dolan, 71, would preside over the team’s first championship since 1973 — nearly 19 years before New York’s mayor, Zohran Mamdani, was even born.
Could all be forgiven, if not forgotten, by the basketball-crazed city?
“Everyone loves a winner, and Jim Dolan sure looks like a winner right now,” said Kathryn Wylde, a longtime New York power broker who has worked on behalf of the city’s top corporations. “I suspect we are ready to forgive his grudge matches.”
Well, maybe not everyone.
“He’s the owner representing icons of Manhattan and the city at large, and to be so unloved — people love to hate him,” said Brad Hoylman-Sigal, the Manhattan borough president and a staunch critic of Mr. Dolan’s. “I don’t think it applies more aptly to anyone else than Jim Dolan.”
The public criticism of Mr. Dolan, whose representatives did not respond to requests for comment, began from almost the moment he was handed control of the Knicks by his father, Charles Dolan, a cable TV titan who had used his company, Cablevision, to buy Madison Square Garden, including the Knicks and Rangers.
The years of jeers have done little to dent Mr. Dolan’s business empire, which includes numerous other New York City treasures: Radio City Music Hall, the Beacon theater and the Christmas Spectacular live production starring the Radio City Rockettes. And he spent $2.3 billion to build the high-tech Las Vegas Sphere, which opened three years ago to rave reviews. Last year, defying skeptics, the Sphere turned a profit.
But fans bemoaned his decisions on and off the court.
He once fired an employee after she reported being sexually harassed by Isiah Thomas, the team’s president of basketball operations from 2003 to 2008, under whose watch the Knicks remained rudderless. She sued and was paid millions in a settlement after a jury ruled that she was sexually harassed and improperly fired. He also extended Mr. Thomas’s contract not long after the suit became public, generating widespread criticism. Then, in 2015, he hired Mr. Thomas again as president of the New York Liberty, a team in the Women’s National Basketball Association.
In 2015, Mr. Dolan received a snarky email from a 73-year-old fan who encouraged him to sell the team. In his reply, Mr. Dolan called the fan “a sad person” and wondered whether he was an alcoholic.
“Just guessing but ill bet your life is a mess and you are a hateful mess,” Mr. Dolan wrote in his typo-laden response.
In 2018, he barred his employees from doing any business with the radio station WFAN and its parent company after a host criticized him.
And a feud with a former player, Charles Oakley, caused the city to seethe.
Mr. Oakley was a fan favorite who played for the Knicks from 1988 to 1998. On Feb. 8, 2017, he was asked to vacate his courtside seat at Madison Square Garden. Reports varied on the reason, but his relationship with Mr. Dolan had been strained for years. As security guards forcibly removed him, fans chanted “Oakley! Oakley!” He was arrested and charged with three counts of assault. Mr. Oakley later sued Madison Square Garden and no longer attends games there.
“It’s a situation that should have been solved a long time ago from the guy who owns the team,” Mr. Oakley said in a recent interview for this article.
Mr. Dolan’s hardball tactics against his enemies generated more negative headlines. He has installed facial-recognition technology at his venues to bar lawyers who work for companies suing Madison Square Garden Sports, which owns the team.
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In April, Wired magazine and the podcast “Pablo Torre Finds Out” published a joint investigation, which found that Mr. Dolan’s security teams had tracked and cataloged sports fans, employees, children and personal critics.
He has routinely defended the policies, saying that barring the lawyers litigating against his company, for example, protected against improper disclosure and discovery.
The Knicks’ fortunes, and by extension Mr. Dolan’s reputation, began to improve when he hired Leon Rose, a high-profile agent, as the team’s president in March 2020.
“He needed somebody that was powerful enough in what he did, whether it was a coach, a former coach or, in this case, a really powerful agent like Leon Rose, who he could kind of hand the reins to and say, ‘I trust you with this,’” said Chris Herring, author of “Blood in the Garden: The Flagrant History of the 1990s New York Knicks.”
In 2022, Mr. Rose signed his godson, the 6-foot-2 guard Jalen Brunson, to a four-year, $104 million contract (not long after hiring Mr. Brunson’s father, one of Mr. Rose’s former clients, as an assistant coach). And Mr. Brunson became a savior of sorts. The Knicks have made the playoffs in each of Mr. Brunson’s four seasons with the team.
That winning streak has even made a mark in New York politics. In the state capitol, a push two years ago to compel the Madison Square Garden arena to pay more taxes — it currently receives millions of dollars in exemptions — stalled amid a flurry of Knicks victories.
The logic among lawmakers: not while the Knicks are winning.
Now, the Knicks are in the team’s first finals since 1999, filling Knicks fans with euphoria.
Not everyone has had a change of heart about Mr. Dolan. Michael Rapaport, the actor and director who was born in New York City, is a lifelong Knicks fan and directed a 2014 documentary called “When the Garden Was Eden.” In a phone interview on Saturday, he predicted that if the Knicks won the championship, Mr. Dolan would be booed. “And I think he should be booed because of the way he’s treated fans, the way he’s treated New Yorkers,” he said.
Still, in the past few weeks, Mr. Dolan experienced something he hadn’t in a while — positive news coverage.
After the Knicks won the Eastern Conference Finals in Cleveland last week, giving the team a spot in the finals, Mr. Dolan declined to accept the trophy during the televised celebration, bucking the custom for owners of the winning team. Instead the trophy was handed to the Knicks’ star player, Mr. Brunson. “I thought that was such a classy move,” said Craig Carton, a radio host with WFAN.
Last week, The New York Post’s Page Six reported that in Cleveland, Mr. Dolan personally made sure that the filmmaker and Knicks superfan Spike Lee, who previously feuded with Mr. Dolan, could be part of the Knicks’ Eastern Conference championship celebration. The Post declared the Dolan-Lee feud over.
And he has caught the eye of another longtime New Yorker who loves to hold a grudge.
President Trump has said he will attend a finals game and recently offered his own endorsement of Mr. Dolan when he called into a morning radio show.
“I get along with Jim Dolan, and I think he’s a really nice guy,” Mr. Trump said, “and he’s entitled to a good team because he’s — he’s suffered a little bit.”
Tania Ganguli writes about money, power and influence in sports and how it impacts the broader culture.
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