Biggest Red Sox Trades Ever: The Deals That Changed Boston Baseball

The Red Sox have been at the center of some of the most shocking trades in MLB history.

In 2025, the Red Sox agreed to a stunning deal with the Giants, sending Rafael Devers, once considered a franchise cornerstone, to San Francisco. The trade was unavoidable because Devers refused to shift from third base to first base after Boston acquired Alex Bregman.

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The Devers trade was just the latest deal involving the Red Sox that altered the future of baseball.

Here are some of the trades that have defined the Red Sox over the years.

Revisiting the biggest Red Sox trades ever

Babe Ruth

The most obvious trade that still upsets Boston sports fans? The infamous transaction that created the “Curse of the Bambino.”

Harry Frazee sold Ruth to the Yankees in order to finance his Broadway musical interests. It was one of the biggest blunders in Red Sox history, as Ruth went on to become a Yankees legend. The “Curse of the Bambino” was finally lifted after 86 years when Boston won the 2004 World Series.

Pedro Martinez, Jason Varitek and Derek Lowe

The Red Sox had a big 1997, as the team traded pitcher Heathcliff Slocumb to the Mariners for two prospects. Those prospects? Varitek, the eventual captain of the team, and Lowe, a key piece of the 2004 championship roster.

A few months later, the Red Sox, in desperate need of a replacement for Roger Clemens, traded Carl Pavano and Tony Armas Jr. for Martinez. He became a Boston legend, winning back-to-back Cy Young awards in 1999 and 2000 and a title in 2004.

Nomar Garciaparra

Garciaparra was the heart of the franchise for nearly a decade. However, injuries, disputes with the front office and defensive struggles signaled the end of his time in Boston.

The Red Sox sent him to the Cubs in 2004 as part of a four-team trade, bringing in Orlando Cabrera and Doug Mientkiewicz.

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Mookie Betts

There is no way around it. Trading Betts was a disaster for the Red Sox.

Uneasy about committing to a long-term deal, the Red Sox moved Betts and David Price to the Dodgers for Jeter Downs, Alex Verdugo and Connor Wong. A generational player, Betts has won three rings in Los Angeles.

Jeff Bagwell

While Bagwell never donned a Red Sox uniform, he’s one of the biggest “What Ifs” in the club’s history.

The Red Sox traded Bagwell, a Boston native, to the Astros for reliever Larry Andersen, who made just 15 appearances before leaving in free agency. Bagwell, meanwhile, went on to have a Hall of Fame career.

Red Sox trade steals vs. disaster deals

While fans often recall the damage of the Ruth and Betts deals, sacrificing key players has ultimately helped the Red Sox in other trades.

Following a massive collapse, the Red Sox traded Josh Beckett, Adrian Gonzalez, Carl Crawford and Nick Punto to the Dodgers in 2012 for James Loney and others. What they got wasn’t nearly as important as the money they unloaded.

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In the offseason, the team signed Shane Victorino, Mike Napoli, Jonny Gomes, David Ross, Koji Uehara and Ryan Dempster, all key players on Boston’s 2013 championship squad.

In other transactions, sacrificing key players led to headaches.

After the Betts trade was completed, Verdugo stayed in Boston for a few seasons, but he was traded to the Yankees in 2023. Downs only played 14 games for the Red Sox, while Wong hit .190 in 2025.