James Dolan: Will a Championship Transform His Legacy with the Knicks?

James L. Dolan has owned the New York Knicks for nearly three decades. Throughout much of this time, the team struggled in the N.B.A. rankings.

Mr. Dolan took charge of the Knicks in 1999, during which they reached the championship round of the N.B.A. playoffs. Over the following 23 years, they managed to make the playoffs only seven times. In 2019, the team’s poor performance led to a Bloomberg headline questioning if Dolan was the worst owner in professional sports.

Dolan’s reputation in New York City was similarly rocky. He often clashed publicly, and at times legally, with fans, employees, city leaders, and players.

Recently, however, the Knicks have seen a remarkable improvement. They now stand on the brink of winning a championship. The team will compete against the San Antonio Spurs in the upcoming N.B.A. finals, beginning Wednesday. If they win the series, Dolan, now 71, would oversee the Knicks’ first championship victory since 1973, well before New York’s current mayor, Zohran Mamdani, was born.

“Everyone loves a winner, and Jim Dolan sure looks like a winner right now,” said Kathryn Wylde, a prominent New York figure who works with the city’s top corporations. “I suspect we are ready to forgive his grudge matches.”

Nevertheless, not all share this sentiment.

Brad Hoylman-Sigal, the Manhattan borough president and a vocal critic of Dolan, remarked, “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.”