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1992
It was one of the worst deals in White Sox GM Ron Schueler’s career, as he traded pitcher Melido Perez and two minor leaguers to the Yankees for Steve Sax. Schueler envisioned a devastating 1-2 punch at the top of the order in Tim Raines and Sax, followed by Frank Thomas and Robin Ventura. It never happened, as Sax suddenly forget how to hit and was gone from the team by late April 1994. Making matters worse is that one of the minor league pitchers dealt to New York was Bob Wickman, who’d go on to become a top relief pitcher and All-Star.
Sax did have one moment of glory with the White Sox. On May 5, 1993 in Milwaukee he made an incredible catch in left field on a ball hit by Bill Doran with the lead run on base. It happened in the eighth inning, when Sax broke back and to his left on the drive and caught the ball with his right arm extended. The angle and momentum caused him to tumble and he lost the ball out of his glove on the way down. Just before hitting the ground, he snagged the ball with his bare left hand, holding it up to the umpire after he hit the grass. That saved a run, and the Sox won the game, 3-1, on a Ventura home run in the top of the ninth inning.
2002
After one injury-plagued, controversial season with the White Sox, pitcher David Wells signed a contract with the Yankees. Wells won only five games in 2001 for Chicago. Naturally, he then turned around and won 61 games over the next four years with New York, San Diego and Boston.
The White Sox did get some revenge by beating Wells in Game 2 of the 2005 ALDS, 5-4, when he was pitching for the Red Sox.