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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HOUSTON, TX – AUGUST 05: Preparations begin as the Houston Astros honor Jeff Bagwell for his induction into the National Baseball Hall of Fame at Minute Maid Park on August 5, 2017 in Houston, Texas. (Photo by Bob Levey/Getty Images)
HOUSTON, TX – AUGUST 05: Preparations begin as the Houston Astros honor Jeff Bagwell for his induction into the National Baseball Hall of Fame at Minute Maid Park on August 5, 2017 in Houston, Texas. (Photo by Bob Levey/Getty Images) /

2. Jeff Bagwell to the Astros, 1990

  • Astros get: Jeff Bagwell
  • Red Sox get: Larry Andersen

There have been Hall of Famers traded — and then there’s this trade. At the end of August in the 1990 season, the Red Sox dipped down to their Double-A roster to make a trade for Houston Astros reliever Larry Andersen. At the time, Andersen was one of the best setup men in baseball. He had a 1.54 ERA in 87.2 innings in 1989 and was working on a 1.95 ERA in 73.2 innings for Houston in 1990.

The Red Sox were in a playoff race (they held on), so this trade does make some sense in hindsight. Andersen gave them a 1.23 ERA in 22 innings down the stretch. Bagwell was a low-upside college player with a squatty batting stance. Sure, he had a .333/.422/.457 line at Double-A in 1990, but was not viewed as a power threat at a premium position.

Andersen bolted the Red Sox for San Diego after the year, while Bagwell made his MLB debut in 1991, slashing a respectable .294/.387/.437 with 26 doubles, 15 home runs and seven steals to win the NL Rookie of the Year. That was just the beginning for Bagwell.

For the decade from 1991 to 2000, Bagwell hit .305/.417/.552 with 310 home runs, 1,093 RBI and 167 stolen bases. He also walked nearly 1,000 times and won the NL MVP and Gold Glove in 1994. Bagwell was the total package at first base and became the first first baseman to produce a 30-30 season, which is a feat he accomplished twice. Teams rarely lose a trade this badly when they give up a prospect from Double-A, but Bagwell’s power finally caught up with his elite plate discipline and ability to hit to all fields.