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The Red Sox's Risky Moves: A Look at Their Most Regrettable Trades
Boston, Massachusetts, USASunday, June 22, 2025
In 1988, the Red Sox traded Curt Schilling and Brady Anderson to the Baltimore Orioles for Mike Boddicker. Boddicker was a useful addition to the Red Sox rotation, but the cost was high. Schilling went on to have a Hall of Fame career, winning 216 games and striking out more than 3, 000 batters. Anderson also had a good career with the Orioles.
In 1990, the Red Sox traded Jeff Bagwell to the Houston Astros for Larry Andersen. Bagwell became a franchise legend in Houston, earning four All-Star selections and an MVP award. He also became a Hall of Famer. Andersen was good for the Red Sox, but not good enough to make up for losing Bagwell.
More recently, the Red Sox traded Mookie Betts to the Los Angeles Dodgers. Betts was on his way to becoming one of the greatest Red Sox players of all time. Instead, he's now a two-time World Series champion with the Dodgers. This trade was seen as a mistake by many Red Sox fans.
The Devers trade could become another regrettable move for the Red Sox. Giants fans are hoping it will, and they have a lot of history on their side. Only time will tell how this trade will turn out, but the Red Sox have a history of making trades that don't go as planned. It's important to learn from the past and make better decisions in the future. The Red Sox have a lot of work to do if they want to avoid making more regrettable trades.
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