1. Milt Pappas and two others for Frank Robinson

The Reds, looking to improve their rotation, traded future Hall-of-Famer Frank Robinson to the Orioles in 1965 for Milt Pappas -- a deal that is considered one of the most lopsided in baseball history. Pappas had marginal success after leaving Baltimore, and Robinson starred once he got here. He hit for the Triple Crown and was named MVP in his first season, and would help the Orioles win two World Series titles.
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