Age: 51
Title: Chairman, Madison Square Garden
Pro: Willing to spend for talent, as shown by the bloated payrolls for the New York Knicks and Rangers. Intensely loyal to his subordinates.
Con: One subordinate, Isiah Thomas of the New York Knicks, has grossly underachieved. Most playoff-starved Knicks fans desperately want Dolan to sell the team. The temperamental boss also fronts a band, JD and the Straight Shot, that is very, very bad.