15 worst trades in New York Yankees history

New York Yankees v Toronto Blue Jays
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13. July 13, 1987: Yankees "Go For It" at 1987 Trade Deadline, Trade Bob Tewksbury for Steve Trout

The son of former MLB pitcher Dizzy Trout (petition: MLB needs more Dizzies), Steve was a solid left-hander in the early '80s who helped push the 1984 Cubs to the cusp of the World Series. Flanked by Rick Sutcliffe and Dennis Eckersley, he pitched 8.1 awesome innings in Chicago's Game 2 triumph over the Padres, but the Cubbies were unable to close out the series, and Trout was left to chase rings elsewhere.

By July 1987, Trout was midway through a heater with the Cubs, pitching back-to-back complete game shutouts in Chicago immediately before being dealt to the Bombers to solidify their staff for a potential playoff run led by MVP candidate Don Mattingly. Unfortunately, Trout succumbed to Ed Whitson Disease after joining the Bombers and busted immediately, walking 37 men in 46.1 innings and posting a 6.60 ERA. He was salary dumped to the Seattle Mariners after the season ended, where he spent two more extremely poor years before retiring.

The prospect they surrendered? The rarely-discussed but extremely solid Bob Tewksbury, who went 110-102 with a 3.92 ERA in his career, but who posted just 10 of those wins with the Yankees before being ding-dong-ditched midway through a tough '87 season. He rebounded, of course, making the All-Star team in 1992.

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