Cleveland outfielder Brian Giles. If you don’t know the story, it’s a little depressing.
In 1998 Cleveland traded away a young, productive outfielder Brian Giles for middle reliever Ricardo Rincon. Rincon would spend the next four seasons with the Tribe and was pretty good, with a 3.73 ERA/1.322 WHIP/126 ERA+ over 154 innings. Cleveland needed the arm. Those Cleveland teams always needed arms. But in retrospect, it was still not worth losing Giles for.
Following the trade from Cleveland, Giles would spend 11 more seasons in the majors and was one of the better outfielders in the National League. He would average 23 HR a season, with a .401 OBP and 138 OPS+. He would be a two-time All-Star selection and earn Top 25 MVP votes five times. He even snuck in four seasons with at least 10 stolen bases. His mix of pop, speed, and on-base skills made him a very special talent that…gosh…would have looked nice in those late-90s Cleveland line-ups.