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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CHICAGO, IL – SEPTEMBER 22, 1990: Ryne Sandberg #23 of the Chicago Cubs bats against the New York Mets during a game on September 22, 1990 in Chicago, Illinois. (Photo by Ronald C. Modra/Sports Imagery/Getty Images)
CHICAGO, IL – SEPTEMBER 22, 1990: Ryne Sandberg #23 of the Chicago Cubs bats against the New York Mets during a game on September 22, 1990 in Chicago, Illinois. (Photo by Ronald C. Modra/Sports Imagery/Getty Images) /

6. Ryne Sandberg to the Cubs, 1982

  • Cubs get: Ryne Sandberg, Larry Bowa
  • Phillies get: Ivan DeJesus

The thought that Larry Bowa being in a tiff with management could cause the front office to trade a future Hall of Famer is laughable today, but that’s exactly what the Philadelphia Phillies did in 1982. They shipped Bowa and a prospect named Ryne Sandberg to the Chicago Cubs for a light-hitting infielder named Ivan DeJesus.

Sandberg would go on to become one of the most iconic players in Cubs history, right up there with Ernie Banks and Ferguson Jenkins. He played 15 seasons for the Cubbies and helped redefined what a second baseman could be expected to do offensively. For a time, he was the highest-paid player in baseball, which would have been unheard of for a second baseman in the preceding decades.

With the Cubs, Sandberg was a 10-time All-Star with nine Gold Gloves and seven Silver Sluggers. He also won the NL MVP award in 1984 while nearly pushing the Cubs to the World Series. He led the league with 114 runs and 19 triples that season and followed it up by hitting .368 in the NLCS.

Most of Sandberg’s time with the Cubs was defined by losing and futility. They only went to the playoffs twice in 15 years and were almost always below .500 during his time with the team. When Sandberg retired, his 277 home runs were an MLB record for second basemen.