Top 25 MLB trades of all time

NEW YORK, NY - APRIL 09: Pitcher Noah Syndergaard #34 of the New York Mets delivers a pitch against the Miami Marlins during the first inning of a game at Citi Field on April 9, 2017 in New York City. (Photo by Rich Schultz/Getty Images)
NEW YORK, NY - APRIL 09: Pitcher Noah Syndergaard #34 of the New York Mets delivers a pitch against the Miami Marlins during the first inning of a game at Citi Field on April 9, 2017 in New York City. (Photo by Rich Schultz/Getty Images) /
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TORONTO, ON – OCTOBER 23: Joe Carter #29 of the Toronto Blue Jays swings and watches the flight of his ball as he hit a game winning and World Series winning three-run home run in the bottom of the ninth inning against the Philadelphia Phillies during game 6 of the World Series on October 23, 1993 at Exhibition Stadium in Toronto, Ontario. Toronto won the series 4 games to 2. (Photo by Focus on Sport/Getty Images)
TORONTO, ON – OCTOBER 23: Joe Carter #29 of the Toronto Blue Jays swings and watches the flight of his ball as he hit a game winning and World Series winning three-run home run in the bottom of the ninth inning against the Philadelphia Phillies during game 6 of the World Series on October 23, 1993 at Exhibition Stadium in Toronto, Ontario. Toronto won the series 4 games to 2. (Photo by Focus on Sport/Getty Images) /

21. Joe Carter and Roberto Alomar to the Blue Jays, 1990

  • Blue Jays get: Joe Carter, Roberto Alomar
  • Padres get: Fred McGriff, Tony Fernandez

The MLB trade where everyone involved wins or turns out to be a solid player with a long career is exceedingly rare. This blockbuster trade in 1990 had a Hall of Famer in Roberto Alomar, a near-500-homer hitter in Fred McGriff, an eventual World Series hero in Joe Carter and one of the best defensive shortstops in MLB history in Tony Fernandez. These type of trades with established MLB stars on both sides switching teams rarely happen today.

The Toronto Blue Jays come out as the winner in this trade because they won the World Series with Carter and Alomar. The San Diego Padres only got two-plus years out of McGriff and Fernandez, but they played well in their time with the team. Fernandez actually ended up back with Toronto in time to win the 1993 World Series and hit .333 in the win over Philadelphia.

Carter made the All-Star team six times as a member of the Blue Jays and won two Silver Sluggers. In his seven years with the franchise, Carter failed to drive in 100 runs only once and went over 25 home runs every year but one. From the age of 26 to the age of 37, Carter averaged 31 home runs and 113 RBI on a per-162 basis. He didn’t walk much or hit for average, but Joe Carter was one of the best run producers of the 1990s.

Roberto Alomar played for seven teams in his 17-year career, but played the longest with the Blue Jays. He became the first player to wear a Jays cap on his Hall of Fame plaque. Alomar hit .307/.382/.451 in five years with Toronto, made the All-Star team every year, won five Gold Gloves and won a Silver Slugger. He hit .480/.519/.640 in the 1993 World Series.