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When your favorite team loses a game, you’ll blame dubious factors from “bad luck” to corrupt refs. But if they keep losing year after year, there’s only one person you’ll blame: The know-nothing, greedy, egomaniac owner. And often you’d be correct, as Playboy’s Smoking Jacket explains in this history lesson on incompetent rich guys in pro sports…
Jeffrey Loria: Montreal Expos (1999-2002) / Miami Marlins (2002-present)
If you are looking for a man to come into your city and run your baseball team into the ground, Jeffrey Loria is your guy. He’s done it twice already. Loria will buy your team and hold taxpayers hostage, refusing to bring pay for top talent until a new stadium is built, all the while flirting with other markets. No wonder he’s the most hated man in baseball.
Charles Comisky: Chicago White Sox (1901-1931)
Comisky was a famed cheapskate who nickel-and-dimed his own players so severely they grew to hate the man. The players’ distaste for Comisky’s miserliness directly led to eight of them throwing the 1919 World Series for some extra dough — provided by mobsters who bet against them. It’s the biggest scandal in Major League history and Comisky’s legacy.