1. Harry Frazee, Red Sox
Baseball has always been a business, as evidenced by Frazee’s tenure as owner of the Sox. He bought the team for $400,000 in 1917 and sold it for $1.5 million in 1923, peddling his best players in the meantime to finance his theatrical investments. His favorite trade partner was the Yankees, who received Carl Mays, Herb Pennock, Everett Scott, and infamously, Babe Ruth. After Ruth’s departure in 1919, the team wouldn’t reach .500 again until 1934, while the Yankees won four World Series titles during that period. Not even the 1918 World Series title, which was won with players inherited by Frazee, excuses his moves as the owner.
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