For most of James Dolan’s tenure in charge of the New York Knicks since he became Madison Square Garden’s chairman in 1999, he has been an easy punching bag for Knicks fans—and much of the damage was self-inflicted. But now, after one magical spring, that turbulent past might be water under the bridge. The Knicks are NBA champions for the first time in 53 years, a moment many fans never thought would be possible with Dolan in charge.

The 71-year-old Cablevision heir also has plenty of reason to celebrate off the court. Forbes recently valued the Knicks at $9.75 billion—No. 3 in the NBA—and Dolan’s NHL team, the Rangers, at $4 billion, the second-best mark in hockey. While that combined total of $13.75 billion easily outpaces the $9.26 billion market cap of the publicly traded MSG, the stock is up 103% over the past year. Meanwhile, Dolan’s other company, Sphere Entertainment, which owns the Sphere just off the Las Vegas Strip and the MSG regional sports TV and radio networks, has seen its share price soar 291%.

The hot streak has the family’s fortune up to $7 billion, according to Forbes estimates, divided among Dolan and his five siblings’ families. (The total does not include the family of Dolan’s late uncle Larry Dolan, a successful lawyer in Ohio who bought the Major League Baseball team now known as the Cleveland Guardians in 2000 and passed control to his son Paul.)

The remarkable turnaround of the Knicks, who before this run had reached the playoffs only ten times since their last appearance in the NBA finals in 1999—the same year James Dolan took over as MSG chairman—began with their combative owner stepping back from the limelight and hiring Leon Rose as the team’s president of basketball operations in 2020. At a time when Dolan was instructing security to detain fans chanting “sell the team” at Knicks home games, he was also apparently taking the criticism to heart, giving Rose, a former CAA basketball agent, the time and space to patiently build a championship-caliber roster.

Rose signed Jalen Brunson, an underappreciated budding star whom the Dallas Mavericks let walk away, as a free agent in 2022, and he has since traded for supporting pieces Karl-Anthony Towns, O.G. Anunoby, Mikal Bridges and Josh Hart. Only Towns had been an All-Star before joining the Knicks.

“There were times when we’ve reached for that shiny, sparkly object, especially when things weren’t going well,” Dolan acknowledged on Brunson and Hart’s Roommates Show podcast in March 2025. “What I learned over time is that it doesn’t work. You really have to do the fundamentals, the basics. You’ve got to build a team; you’ve got to build an organization.”

Dolan has been used to getting what he wants for most of his life. His father, Charles Dolan, was a communications mogul who founded HBO, selling his stake to Time Inc. and using some of the proceeds in 1973 to found Cablevision, a cable television company serving the New York metropolitan area. Cablevision, which went public in 1986, was acquired by European telecommunications firm Altice in 2016 for $17.7 billion.

In 1994, Cablevision and engineering conglomerate ITT partnered to buy Madison Square Garden, the MSG Network and the Knicks and Rangers from Viacom for $1.1 billion. Three years later, Cablevision bought out ITT’s half of the business for $650 million, taking full control.

At the time of Charles Dolan’s death in 2024 at age 98, Forbes estimated his net worth at $5.4 billion.

James Dolan grew up in the Long Island suburb of Massapequa and graduated from SUNY New Paltz with a degree in communications in 1979, when he went to work for his dad at Cablevision. He told Forbes in 1999 that he decided to give the company five years to see if he liked it, and then extended that timeline to ten years. He never left.

Dolan worked his way up through the company, starting an advertising sales division, but also struggled with drug and alcohol abuse through his mid-30s. He went to a rehab clinic in 1993 and has spoken openly about his sobriety since then. In 1995, his father handed him the reins as CEO of Cablevision, a role he held until its 2016 sale, but he knew his peers scoffed at his nepotistic rise.

“You want someone to underestimate you,” he told Forbes in 1999. “You get more flexibility of movement.”

That interview, however, came at the start of two decades of futility for the Knicks, littered with questionable personnel decisions. The team cycled through 13 full-time or interim head coaches from 2001 to 2020, a 20-year span in which they managed to win only one playoff series. The Knicks also overpaid in trades for players like Eddy Curry, Carmelo Anthony and Andrea Bargnani before luring Hall of Fame coach Phil Jackson out of retirement in 2014 with a five-year, $60 million contract to run their basketball operations. That move didn’t work, either.

In one of the lowlights of Dolan’s tenure, Charles Oakley, a franchise icon who played for the Knicks during their 1990s heyday, was physically removed from Madison Square Garden during a game in 2017 and charged with trespassing and misdemeanor assault after resisting the arena’s security officers. Oakley sued Dolan for defamation and discrimination based on Dolan’s subsequent comments accusing Oakley of having problems with anger and alcohol, and the feud remains ongoing.

The list of people not welcome in the Garden extends well beyond Oakley. Controversially, Dolan has used facial recognition technology for years to ban lawyers working at firms involved in lawsuits against him, the New York Times reported in 2022.

Even while the Knicks were constantly in the headlines for all the wrong reasons, Dolan proved to be a shrewd businessman. He spun off Cablevision’s entertainment properties, including the Knicks and the Rangers, into a new publicly traded company called the Madison Square Garden Company in 2010, holding on to that business when the rest of Cablevision was sold six years later.

Then, in 2020, the MSG Company further split up its entertainment and sports businesses into separate publicly traded companies while it was designing the Las Vegas Sphere, which opened in 2023 and is now housed under yet another public company, Sphere Entertainment. That company has been a smashing success, quadrupling in value since the end of 2024 while hosting residencies for acts like the Eagles and the Backstreet Boys. A lifelong music lover who moonlights as the lead singer for his own band, JD & The Straight Shot, Dolan has prioritized the Sphere in recent years as his personal passion, perhaps allowing the Knicks to run more smoothly without his day-to-day influence.

Now, Dolan is planning one more spinoff, after MSG Sports filed a proposal in May to split the Rangers from the Knicks. Dolan has insisted he has no interest in selling the clubs outright, but the separation of the teams would make it easier for him to part with a stake in one or the other.

Although Dolan’s reputation has improved alongside the Knicks’ fortunes, he still couldn’t resist starting one more fight during this year’s NBA finals, this time with New York City mayor Zohran Mamdani. Dolan, who hosted President Donald Trump in his suite for Game 3 of the finals last Monday, called Mamdani and police commissioner Jessica Tisch “party poopers” while complaining about the permitting process that led to the cancellation of watch parties outside Madison Square Garden.

Dolan has been unapologetically abrasive through the highs and lows of his tenure as owner, but in the eyes of millions of New Yorkers, winning may cure all.

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