25. George Steinbrenner
George Steinbrenner was nicknamed “The Boss” for good reason. His personnel carousel spun like an Andy Pettitte curveball. In the first 23 seasons of Steinbrenner ownership, he changed managers a ridiculous 20 times. On top of that, eGeorge also employed 11 separate general managers. His bombastic, big-spending ways played a major role in driving up player salaries to absurd levels. He feuded with big-name players, deriding Dave Winfield as “Mr. May” for his lagging production in the postseason and demanding haircuts by such players as Thurman Munson, Bobby Murcer, Sparky Lyle, Goose Gossage and Don Mattingly.
Steinbrenner’s ego also got exposed off the field, such as when he pleaded guilty in 1974 to making illegal contributions to Richard Nixon’s re-election campaign, resulting in a 15-month suspension from the Yankees. Sixteen years later, he was banned permanently from day-to-day management of the team after paying a gambler to dig up dirt on Winfield (Steinbrenner was reinstated in 1993). On top of it all, the Yankees went 14 years without a playoff appearance. But it turned around in 1995, when they began a run of 13 consecutive playoff appearances. For all of his problems and negative publicity, the Yankees under Steinbrenner won 11 pennants and seven World Series. Can’t hate a winner. Though the rest of the league sure as hell did.