Trades are the best and worst thing in baseball. Sometimes your favorite team lands a player who can help win a World Series, and sometimes that same team trades for a prospect who turns out to be a dud. Here are the 20 worst trades in baseball history. Agree? Disagree? Leave your comments and let’s discuss!
20. St. Louis Cardinals trade Steve Carlton to the Philadelphia Phillies for Rick Wise (1972)
“Lefty” had a sensational career with the Phillies and was inducted into the Baseball Hall of Fame in 1994. This was certainly an “unwise” deal for St. Louis.
19. Toronto Blue Jays trade Roy Halladay to the Philadelphia Phillies for Kyle Drabek, Travis d’Arnaud, and Michael Taylor. (2009)
It was surprising that the Blue Jays let go of their star pitcher, who went on to pitch exceptionally well with the Phillies.
18. Kansas City Royals trade David Cone three times (1987, 1995 2x)
A Kansas City native, Cone was traded to the Mets for Ed Hearn and others in a lopsided deal. Then, Kansas City traded him again in 1995 to the Blue Jays in another epically bad deal.
17. Philadelphia Phillies trade Ryne Sandberg and Larry Bowa to the Chicago Cubs for Ivan DeJesus (1982)
Sandberg was inducted into the Baseball Hall of Fame in 2005.
16. Minnesota Twins trade Rod Carew to the California Angels for four players (1979)
Even though he was 33 at the time, Carew went on to have six more All-Star seasons before retiring.
15. Seattle Mariners trade Randy Johnson to the Houston Astros for Carlos Guillen, Freddie Garcia, and John Halama (1998)
Garcia was a respectable pitcher for Seattle, but none of them could match up to the greatness of Johnson.
14. New York Mets trade Tom Seaver to the Cincinnati Reds for four players (1977)
Tom Terrific went on to have a tremendous second career in Cincinnati, while the Mets string of losing seasons began after he left.
13. Kansas City Athletics traded Roger Maris and two others to the New York Yankees for Don Larsen and three other players (1959)
The Cleveland Indians sent Maris to Kansas City in 1958, and then Kansas City shipped Maris to the Yankees, and the rest became home run lore.
12. Seattle Mariners trade Jason Varitek and Derek Lowe to the Boston Red Sox for Heathcliff Slocumb (1997)
Varitek and Lowe became mainstays in the Red Sox lineup and team leaders in the clubhouse, which helped Boston break the Curse of the Bambino.
11. Oakland Athletics trade Mark McGwire to the St. Louis Cardinals for three players (1997)
Oakland didn’t want to pay McGwire going into free agency, so they moved him to St. Louis, where his power hitting energized a game that had been hurt by the strike.
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.
