SPORTS
The Red Sox's Risky Moves: A Look at Their Most Regrettable Trades
Boston, Massachusetts, USASun Jun 22 2025
The Boston Red Sox have a history of making trades that didn't go as planned. The recent move sending Rafael Devers to the San Francisco Giants is just the latest example. It's too early to say how this trade will turn out, but early signs aren't great for Boston. When a team trades away a star player who is still in their prime, it usually doesn't end well for the team making the trade. This is especially true when the star player is one of the best hitters in the league.
The Red Sox have a history of making bad trades. Let's look at some of the worst ones. In 1916, the Red Sox traded Tris Speaker to the Cleveland Indians. Speaker was one of the best players in the game, but he refused to sign his contract for the 1916 season. The Red Sox traded him to Cleveland just months after he helped them win the World Series. Speaker went on to have a great career with Cleveland, while the players the Red Sox got in return were not as good.
Another infamous trade happened in 1919. The Red Sox traded Babe Ruth to the New York Yankees. This is often considered the worst trade in baseball history. Ruth went on to become one of the greatest players of all time, helping the Yankees win multiple World Series. The Red Sox didn't win another World Series until 2004. This trade changed the course of baseball history and enriched a rival team.
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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questions
Will Rafael Devers miss the Boston weather, or will he finally get to enjoy a real winter?
How do the Red Sox plan to replace the production lost from trading Rafael Devers?
Was the trade of Rafael Devers part of a secret plan to weaken the Red Sox for future seasons?