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Boehringer wound up with the Yankees after he was traded from the White Sox system in March 1994 for southpaw Paul Assenmacher. He emerged as a valuable reliever during New York's World Championship run in 1996, picking up a relief win in Game Two of the Division Series vs. Texas. On November 18th, 1997 he changed teams twice in one day as Tampa Bay selected him in the expansion draft and subsequently traded him to San Diego for infielder Andy Sheets and catcher John Flaherty. On September 16th, 1998 he allowed home run # 63 to Cubs' slugger Sammy Sosa, an eighth-inning grand slam at San Diego's Qualcomm Stadium. Boehringer pitched well when moved into the Padres starting rotation in June 1999, but his season was cut short by a strained rotator cuff, and he was limited to seven appearances in 2000 by tendinitis in his right shoulder.