The Nightmare Trade That Still Haunts Each MLB Franchise

Baltimore Orioles — Curt Schilling

Mitchell Layton/Getty Images

Trade Details: Curt Schilling, Pete Harnisch and Steve Finley to Houston for Glenn Davis

Curt Schilling played for five teams during his 20-year career…and all five teams traded him. Drafted by the Red Sox in 1986, Schilling was shipped to Baltimore in ’88 before reaching the Majors. Throughout three seasons with the Orioles, Schilling started a mere five games, appeared in 44 total games and posted a 4.54 ERA. Baltimore opted to trade the young pitcher to Houston for Glenn Davis. Over the course of three years, Davis hit .247 with 24 HR.

Schilling would go on to win 215 games, became a six-time All-Star and won three World Series after leaving town. Making the trade even worse, Harnisch and Finley both had very nice careers. Harnisch became an All-Star the next season and won 95 more games before retiring. Finley won five Gold Gloves, hit 299 HR, drove in over 1,100 runs, and made two All-Star games following the trade.