Dolan pushed to acquire Carmelo Anthony from Denver in February, surrendering multiple players and draft picks in a deal widely criticized as too costly because Dolan was too eager not to miss out on another star. Donnie Walsh, who had built the Knicks for three years for that kind of big move, was let go in June after pulling off the deal the owner demanded.

Dolan hired 11-time champion Phil Jackson as president on a five-year, $60 million deal, but it never worked out. Jackson tried to install the triangle offense in a league that had evolved past it. The Knicks missed the playoffs every season and Jackson clashed with Anthony

After giving up so much to bring him to the Garden, Carmelo was gone in 2017.

One of the most beloved Knicks of all time, Charles Oakley was sitting courtside when security dragged him out of his seat, arrested him and banned him from the building. It was reportedly on Dolan’s direct orders. The franchise then issued a statement implying Oakley had a drinking problem. NBA Commissioner and legend Michael Jordan had to call Dolan to get the ban lifted.

Oakley sued and eight years later the case is on-going.

Before a game against the Bulls, a season ticket holder outside MSG yelled “Sell the team!” at Dolan. Rather than keep walking, Dolan turned around got in the man’s face and screamed at him,

He confirmed it to Deadspin, adding: “I did call him an a------ because he is an a------.”

Dolan began using facial recognition technology to bar attorneys from MSG venues, which also include Radio City Music Hall, if their firms were suing the company. Thousands of lawyers at roughly 90 firms were affected. When the New York State attorney general warned the practice may violate anti-discrimination laws and the State Liquor Authority threatened to pull the Garden’s liquor license, Dolan went on live television and defiantly defended his decision. He also threatened to shut down liquor sales at Rangers games himself and then held up a picture of the SLA director that included his personal phone number and email address live on air for fans to flood him with complaints.

Dolan sued the Toronto Raptors for $10 million over an analytics staffer he claimed had stolen confidential files. Dolan simultaneously resigned from his league committee positions and wrote to commissioner Adam Silver that “the NBA neither needs nor wants my opinion,” accusing Silver of bias. The suit was quietly dropped in October 2025.

Massage therapist Kellye Croft filed a federal lawsuit alleging Dolan sexually assaulted her in 2013 while his band, JD & The Straight Shot, toured with the Eagles, then arranged a meeting that led to Harvey Weinstein assaulting her. Dolan denied everything. A federal judge dismissed the case in September 2024 on technical grounds, without ruling on the underlying allegations.

The Knicks were in the middle of their best run in two decades. Thibodeau was fired anyway, over the reported objections of Jalen Brunson and Leon Rose. Dolan had reportedly sat in on player exit interviews during the process, which people around the league said they had never seen an owner do.

Dolan broke a two-year media silence with a WFAN radio appearance and declared the Knicks “absolutely” had to reach the NBA Finals and should win it.

Hours later, the Knicks lost to the Detroit Pistons by 31 points.

Maybe he's a prophet. Dolan’s firing of Thibodeau and hiring of Mike Brown has seemingly worked. The Knicks are in the NBA Finals and will face the San Antonio Spurs, looking for their first title since 1973.

Some fans say winning cures all, but other say 25 years of losing, embarrassment and controversy doesn’t wash off that easily. Dolan has said he has no plans to sell. Someone in the family, he said, will own the team. For now, the most controversial owner in New York City sports is one championship series win away from the most unlikely redemption story in New York history.

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This article originally appeared on USA TODAY: James Dolan Knicks ownership has been feuds and 25 years of chaos