Despite their success, the New York Yankees have made some questionable personnel transactions over the years. In 2003, they traded for pitcher Kevin Brown, a 39 year old, who had seen better days. In 2004, Brown won 10 games until he broke his hand punching a wall. Brown was supposed to be a big-game pitcher. He wasn't. In 1999, the Florida Marlins acquired Mike Lowell from the Yankees. Lowell was solid with the Marlins, and helped them beat the Yankees in the 2003 World Series. He also played for the Red Sox where he was the cornerstone of the team. The list goes on.
Yet, the worst trade of the storied franchise occurred in 1988 when the Bronx Bombers got rid of Jay Buhner. The Yankees sent Buhner and another player to the Seattle Mariners for Ken Phelps.
The teams consummated the trade on July 21, 1988. Buhner was young and just starting his career. Phelps was 33 years old, ancient by baseball standards. During the second half of the 1988 season, Phelps batted a laughable .244 with 10 homers. Buhner played 13 seasons with Seattle, hitting 310 career home runs [source: Rush].