The switch-hitting Wilson was billed as a top prospect for Cleveland before his debut in 1997, but was stuck behind such players as Roberto Alomar and Omar Vizquel. He served as a reserve for three years before being shipped to the Pirates in July 2000 for Wil Cordero. Pittsburgh chose to use Pat Meares and Jack Wilson as their 2001 middle infield, and dealt Wilson to the Yankees in July. He finished the year backing up Alfonso Soriano, Derek Jeter, and Scott Brosius.
Wilson will always be remembered for Game Two of the 1998 AL Championship Series against the Yankees. In the 11th inning, Wilson stood on second base and Travis Fryman hit a dribbler up the first base line. Tino Martinez tossed it to a covering Chuck Knoblauch at first, but the throw hit Fryman in the back and was ruled safe. Knoblauch lost control of his emotions and engaged in a shouting match with the umpire, contending that Fryman had run inside the baseline. The ball remained in play while Knoblauch screamed, and Wilson scampered home with the game-winning run.