10. Los Angeles Dodgers trade Pedro Martinez to the Montreal Expos for Delino DeShields (1993): Martinez went on to become one of the greatest pitchers of all time, as DeShields’ career flamed out in Los Angeles.
9. Cincinnati Reds trade Frank Robinson to the Baltimore Orioles for Milt Pappas and two others (1965)
Robinson won the Triple Crown with Baltimore in his first season as well as two World Series rings.
8. Baltimore Orioles trade Curt Schilling, Pete Harnisch, and Steve Finley to the Houston Astros for Glenn Davis (1991)
Not only did Schilling go on to be one of the best pitchers of his generation, but Finley was a mainstay in the Astros lineup for years.
7. Boston Red Sox trade Mookie Betts to the Los Angeles Dodgers for Alex Verdugo, Jeter Downs, and Connor Wong (2020)
Red Sox fans still cheer for Mookie as they know he never wanted to leave.
6. New York Yankees trade Jay Buhner to the Seattle Mariners for Ken Phelps (1988)
You know it’s a bad deal when they make fun of it on Seinfeld.
5. Boston Red Sox trade Jeff Bagwell to the Houston Astros for Larry Andersen (1990)
Jeff Bagwell was inducted into the Baseball Hall of Fame in 2017 and Larry Andersen became the butt of jokes ever since.
4. New York Mets trade Nolan Ryan to the California Angels for Jim Fregosi (1971)
The Mets lost patience with the erratic Ryan and traded him for the 3B they needed in Fregosi. Little did they realize that Ryan would eventually be one of the most dominant strikeout pitchers in history.
3. Detroit Tigers trade John Smoltz to the Atlanta Braves for Doyle Alexander (1987)
Detroit was in win-now mode and traded Smoltz for an established veteran. Turns out they should have been more patient and waited for Smoltz, who had a Hall of Fame career with the Braves.
2. Chicago Cubs trade Lou Brock to the St. Louis Cardinals for Ernie Broglio (1964)
When Brock retired, he was the MLB all-time stolen base leader.
1. Boston Red Sox trade Babe Ruth to the New York Yankees (1919)
There’s a reason they called it the curse of the Bambino.