The Worst Trades In Red Sox History, Ranked
The Boston Red Sox have a long and storied history. They've won nine World Series, including four since 2004. The first five championships came over 100 years ago. They've been around for a long time.
And they've made a lot of big trades. Some have worked wonders in the quest for a championship. Some have backfired miserably.
Here are the five worst trades in Boston Red Sox history.
4. Tris Speaker to the Indians for Sam Jones, Fred Thomas and cash (1916)
Speaker was premier for Boston. He led the AL in WAR three times, including two ridiculous seasons of 10.0 and higher. He won a league MVP in 1912 and was Top 12 in voting four straight years.
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But Red Sox owner Harry Frazee didn't want to pay Speaker, who was one of the top hitters and centerfielders in the first half of the 20th century. So he essentially took a cash deal from Cleveland. This is an unfortunate foreshadowing of Frazee's priorities.
In Speaker's first season in Cleveland, he led the league in hits, doubles, batting average, on-base percentage, slugging, OPS and every other modern metric. He paced the league in doubles five more times, retiring at age 40 as the all-time doubles leader, a mark he still holds.
"Sad" Sam Jones went 16-5 with a 2.25 ERA his second season in Boston but went to the Yankees in 1922 and played 14 more seasons.
3. Jeff Bagwell to the Astros for Larry Andersen (1990)
The Red Sox needed a bullpen arm for a playoff push. So they traded for Andersen, who had a 1.95 ERA in 50 games for Houston. Andersen was even better for the Sox with a 1.23 ERA, though just in 15 games. Boston did make the playoffs, ultimately swept in the AL Championship Series by the Athletics.
Sounds good until you remember that Bagwell, a Boston native, was a touted prospect at Double-A at the time. He immediately won Rookie of the Year honors in 1991, and over his 15 years led the league at some point in WAR, games, runs, doubles, RBIs and walks.
The 1994 AL MVP ultimately hit 449 home runs and batted .297 over 15 seasons, all with the Astros. He's in the Baseball Hall of Fame.
2. Mookie Betts and David Price to the Dodgers for Alex Verdugo, Jeter Downs and Connor Wong (2019)
Betts was a homegrown superstar and beloved 2018 AL MVP for the Red Sox, guiding Boston to the 2018 World Series championship over the Dodgers. But off-season contract disputes led the Sox to trading him, along with the veteran pitcher Price, to the Dodgers for a handful of players.
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For the Dodgers, Betts led the NL in WAR in 2020 and 2023 and was a steady leader in their back-to-back World Series championships. He remains the everyday starting shortstop. Price was at the tail end of his career but was a reliable bullpen piece in 2022 (2.45 ERA) before retiring at age 36.
Verdugo batted .308 for the Red Sox in 2020, but his average dropped in each of his five seasons with the team. He never hit more than 13 home runs and left after four seasons, retiring in 2025 at age 29. Wong is currently the No. 3 catcher on the Boston depth chart. Downs batted 82 in 20 career games.
1. Babe Ruth to the Yankees for cash (1919)
The gold standard for bad trades. Ruth guided the Red Sox to the 1918 World Series championship, but team owner Harry Frazee traded Ruth to the Yankees for money to finance Frazee's Broadway endeavors.
Boston received no players in the deal.
The "Curse of the Bambino" was born. Ruth revolutionized baseball as a power hitter, became a Yankees legend and helped build one of the strongest dynasties in sports history. The Red Sox didn't get back to the World Series for 86 years.
Related: Red Sox Best Trades In Team History
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This story was originally published June 18, 2026 at 8:07 AM.