James L. Dolan has been the owner of the New York Knicks for nearly three decades. Known for the team’s struggles, the Knicks have been among the worst in the NBA during much of his tenure.

In 1999, the Knicks reached the championship round in Dolan’s first year, yet over the subsequent 23 years, they made only seven playoff appearances. In 2019, they held the worst NBA record, leading to Bloomberg’s headline questioning Dolan’s competence as a sports owner.

Dolan’s reputation in New York City has been marred by frequent public disputes with fans, staff, politicians, and players. Despite these challenges, the Knicks have undergone a notable transformation in recent seasons. They are on the brink of a title facing the San Antonio Spurs in the upcoming NBA finals.

A victory in the best-of-seven series would mark the Knicks’ first championship since 1973, long before the current New York mayor, Zohran Mamdani, was born.

“Everyone loves a winner, and Jim Dolan sure looks like a winner right now,” remarked Kathryn Wylde, a prominent figure in New York’s corporate scene. “I suspect we are ready to forgive his grudge matches.”

However, not all share this sentiment.

Brad Hoylman-Sigal, the Manhattan borough president, expressed criticism, noting, “He’s the owner representing icons of Manhattan and the city at large, and to be so unloved — people love to hate him. I don’t think it applies more aptly to anyone else than Jim Dolan.”