Even by the standards of James Dolan’s nightmarish reign over the New York Knicks, 2006 was a dark year. Some argue it marked the worst chapter in the storied – and often turbulent – history of the team. Just nine days before Christmas that season, Dolan’s Knicks were embroiled in a brawl with the Denver Nuggets at Madison Square Garden. The sprawling melee would become the biggest on-court fight in the NBA since the Indiana Pacers–Detroit Pistons scrapped during the Malice at the Palace. That 2006 December night, basketball sank to its most primal state – disjointed men trading punches instead of passes, prioritizing violence over victory. The Garden, once Eden, had wilted into a bacchanalia of banality, with Dolan its Caligula.

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The degradation on display that night embodied the chaos of Dolan’s reign. Statistically, under Dolan’s rule there were worse seasons, like the 17-65 teams in 2014-2015 and 2018-2019. But the 2006 Knicks were an existential disaster on and off the court. After just a single season, Hall of Famer Larry Brown was fired as head coach. Their putrid 23-59 record was the worst in the Eastern Conference. The Knicks’ payroll for the 2005–2006 season was $124m – an impressive $74.5m above the salary cap and $62.3m over the luxury tax.

Even worse, Dolan was shelling out millions for washed-up “names” well past their prime, like Steve Francis and Jalen Rose. The league and NBA fans’ frosty perception of Dolan continues to this day, and it’s easy to see why, given his well-earned reputation as a petty autocrat. Known for kicking out fans who demand he sell the team, banning lawyers in litigation against him, and using facial recognition software at MSG to exclude rivals, Dolan’s thin skin and symbiotic friendships have repeatedly compromised his business’s integrity. His decade-long entanglement with Isiah Thomas, who was accused of sexual harassment by a Knicks executive, embodied the worst of his leadership, while incidents like the 2017 altercation with franchise legend Charles Oakley – who was tackled and removed by Dolan’s security, sparking a public feud – only deepened the franchise’s dysfunction. Oakley still refuses to return to Madison Square Garden without an apology from Dolan.

But it was the situation around Thomas that was perhaps the most dismal point of Dolan’s reign. Anucha Browne Sanders, a former executive for the New York Knicks and a trailblazer as one of the highest-ranking women in the NBA, became the central figure in a landmark legal battle that exposed deep dysfunction within the organization. In January 2006, just days after her abrupt dismissal, Browne Sanders filed a harrowing harassment lawsuit against Thomas, then the team’s head of basketball operations, and Madison Square Garden. The suit alleged that Thomas subjected her to ongoing harassment starting in December 2003, when he joined the organization. The lawsuit also accused Madison Square Garden of retaliating against her for speaking out, claiming she was ousted under the guise of an “investigation” after her lawyer raised the complaint. Eventually, a jury decided MSG and Dolan should pay Browne Sanders $11.6m in damages. Thomas did not face any criminal action over the allegations.

To his credit, Dolan was far ahead of his peers when it came to hiring Black executives and coaches. However, this, too, comes with its complexities, as many of the Black leaders he has selected have proven to be questionable – not because of their race but because of their personal failings. The Knicks were the first team in NBA history with a Black president of basketball operations, general manager, and head coach in Steve Mills, Scott Perry, and David Fizdale. But Mills and Fizdale were awful in their roles. Fizdale recorded a record of 21-83 over parts of two seasons. Mills was fired after building a roster of undersized power forwards and failing to deliver Dolan’s dream of Kyrie Irving and Kevin Durant in the 2019 free-agent bonanza. Not to mention, Thomas held president of basketball operations, GM, and head coach roles while with the Knicks and was the worst in the NBA at all three during the 2000s.

It’s also important to note Brown Sanders was one of the few African American female executives in professional sports, and Dolan dragged her reputation through the mud when she fought back against discrimination and sexual harassment. The buck has always stopped with Dolan.

He had been handed the team on a silver platter by his father in 1999 and between then and 2020, the Knicks amassed a 693-997 record, the worst in the NBA over that period. And then something odd happened: Dolan became a semi-competent owner. 2020-21 was their first winning season since 2012-13 and the first time since then that they had reached the playoffs. They have made now made the playoffs in three of the last four seasons and are currently fourth in the Eastern Conference. 2020 is also the year that Dolan hired Leon Rose, a former agent and executive at talent agency CAA, as president of basketball operations. In the four and a half seasons since hiring Rose, the Knicks have gone 188-151. If 2006 cemented Dolan’s reputation as the NBA’s worst owner, his decision to hire Rose to run the team in 2020 marked the moment he began shedding that title.

So what happened, after 20 years of micro-managing, to make Dolan step back from basketball decisions? You could point to the Las Vegas Sphere, his innovative real estate project that allowed him to tap into his long-gestating creative side, one fronting his jazz band couldn’t satiate. Perhaps Dolan realized he needed a different type of president of basketball operations. He had been scarred by two famous names. The 2014–2017 Phil Jackson era, which Rose was later tasked with cleaning up, mirrored the dysfunction of the 2003–2008 Thomas era a bit too closely. In both cases, Dolan was forced to intervene and fire the man he made president of basketball operations and entrusted with “saving” the Knicks.

The hiring of Rose was risky. The move lacked the splashy name recognition of former NBA champions Thomas and Jackson. While Rose might not have arrived in New York with championship rings, he did possess better first-hand knowledge of how the Knicks have operated under Dolan than anyone. While running CAA, Rose was the agent for many players who came to define the Knicks’ ineptitude and lack of foresight under Dolan. Rose was in the war room with Carmelo Anthony in 2011 when Dolan took over negotiations, offering all the team’s young depth to obtain him. He represented Renaldo Balkman, Andre Bargnani, and Eddy Curry, and each represented real-life memes of Knicks misses. He was in LeBron James’s ear as his agent when Dolan and company clumsy pitched LeBron to come to New York in the summer of 2010.

The Rose hire revealed rare restraint and foresight on Dolan’s part to bring in somebody demanding patience. A hire with no pizazz, just a plan – and that plan often involves bringing in players who suddenly shine when they reach Rose’s Knicks. Jalen Brunson was a solid pro with the Dallas Mavericks; with the Knicks, he has become one of the best players in the league and an MVP candidate. And former No 1 overall pick Karl-Anthony Towns is finally fulfilling his massive potential after being swapped for Julius Randle this summer.

The recruitment of Rose will probably be remembered as Dolan’s best hire, a departure from the flawed judgment he has shown for the past two decades. Suddenly, there is a calm around the Knicks: Rose mimics Dolan’s avoidance of the press and almost always speaks through in-house TV interviews on MSG media. Depending on who you ask, this can be seen as either a good or bad thing – there are few outlandish statements that can disrupt a team but it is also harder for the media to demand answers from management.

Knicks fans will hope Rose secures the long-awaited championship. If that happens, Dolan’s greatest victory would have been knowing when to get out of the way.