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But Dolan, 51, who is also a blues/rock singer, has learned even more about embarrassing defeats during the last few weeks.
Already vilified in the New York press as a rich kid whose dad gave him the Knicks as a plaything, Dolan is now depicted as a boss who tolerates bad behavior and bad language in the office.
In addition, a Dolan family plan to make Cablevision Systems Corp. a private company has been rejected by shareholders.
Cablevision, a dominant player in the New York City area, owns Madison Square Garden, which, in turn, owns the Knicks, the MSG Network, hockey's New York Rangers, the New York Liberty of the Womens National Basketball Association and Radio City Music Hall.
All in all, Dolan may be finding new wisdom in the first lines of one of his bands' songs: "Who told you life would be easy? Who said you would smile every day?"
On Oct. 2, a federal jury in Manhattan found that Madison Square Garden and Knicks coach Isiah Thomas had sexually discriminated against one of its executives.
The verdict came after a trial that made the Knicks front office seem like a locker room where boys were, alas, boys.
The Garden was ordered to pay $8.6 million to the executive, Anucha Browne Sanders. The jury found that the company had created a hostile work environment and that it fired Browne Sanders in retaliation for her complaints about inappropriate language and advances.
The jury ordered Dolan, president and chief executive officer of Cablevision Systems, to pay Browne Sanders $3 million for the retaliatory firing.
His father, Charles F. Dolan, the founder of HBO, is Cablevision's chairman and founder.
On Wednesday, shareholders rejected a $10.6 billion bid by the Dolan family to take Cablevision private. The Dolans had offered $36.26 a share. Some major shareholders said the price was too low.
Charles and James Dolan, who have sometimes feuded, put the best face they could on the rejection, saying in a joint press release:
"We see today's outcome as a vote of confidence in the prospects of Cablevision, its management team, its 20,000 employees and the industry's future."
James Dolan's total compensation for 2006 was $8.71 million, Forbes magazine reported.
Some of his earnings, over $300,000, have gone to political candidates, mostly Democrats. This year he has given to the presidential campaign of Sen. Hillary Rodham Clinton of New York.
Dolan is also the lead singer and rhythm guitarist of JD & the Straight Shot.
According the band's website, mixing business and music gives Dolan "a sense of balance in his life."
The Rocky Mountain News in Denver described the band's first album, as getting "grudgingly good reviews."
The grudging praise sometimes comes from Knicks fans. The team has not had a winning season since 2000-2001, despite a high payroll.
After 2005-2006 losing season, the club found itself in a soap opera feud with its coach of one year, Larry Brown. The melodrama ended with the Knicks buying out Brown's contract for $18.5 million.
Last season, the team won 33 games and lost 49, certainly enough to make Dolan sing the blues.