10 worst Boston Red Sox trades in team history

A long history with plenty of losing must mean the Boston Red Sox have made some mistakes along the way. Indeed, they have.

Red Sox general managers past and present have made some egregious errors in judgment when it came to trading for players. Sometimes they bought a veteran and gave up a future star. In other instances, the Red Sox gave up a major leaguer for prospects that never did a whole lot.

A mix of legendary and ugly, these are the ten worst trades the Red Sox have ever made.

10) Worst Red Sox trade: Jamie Moyer to the Mariners for Darren Bragg

There’s no bragging about this Red Sox trade despite the presence of the most braggadocious player in MLB history in terms of name being present in it, Darren Bragg. At the 1996 trade deadline, the Red Sox acquired him from the Seattle Mariners for starting pitcher Jamie Moyer.

Bragg was a decent outfielder for the Red Sox in his two and a half seasons with them. In fact, his time in Boston was the peak of his long MLB career as a journeyman outfielder.

Speaking of long MLB careers, Moyer spent parts of 25 seasons in the bigs. He was in the middle of his age 33 season when the Mariners acquired him from the Red Sox. The ultimate late bloomer, Moyer did reach free agency after the season ended but would go on to re-sign with the Mariners and would regularly contend for the Cy Young Award well after Bragg was already gone.

It’s hard to blame the Red Sox for this because who would have expected a sixth place finish from him in 1999, a fourth place in 2001, and a fifth place in 2003. If they had only held onto him for one more season, maybe the Red Sox could have had him in the same rotation with Pedro Martinez.

9) Worst Red Sox trade: Acquiring Adrian Gonzalez for Anthony Rizzo and then trading him

Was this actually a bad Red Sox trade? Adrian Gonzalez was an amazing player for Boston. The problem is all of the context around it.

Gonzalez was dealt by the San Diego Padres to the Red Sox on December 6, 2010. Eric Patterson would get paired later on with the initial trade costing Boston Rey Fuentes, Casey Kelly, and Anthony Rizzo.

Gonzalez had a monster 2011 season for Boston shortly after signing a seven-year extension, batting .338/.410/.548 while leading the league with 213 hits. How could this trade possibly be a disaster? He was pretty good in 2012 as well, batting .300/.343/.469 in his 123 games. Then came the problem. The Red Sox had issues and in order to help dump some major salaries off of the payroll, Gonzalez was among the players sent to the Los Angeles Dodgers for not much at all. 

The Red Sox may have won the Gonzalez deal with the Padres, but it did cost them Rizzo who would go on to have a ton of success later on with the Chicago Cubs. They were left without a truly good first baseman which, fortunately, didn’t hold them back from winning the World Series in 2013.

Having this trade on the list is more of a testament to how good the Red Sox have been at avoiding bad trades. As we move on, they’re going to get more painful.

7) Worst Red Sox trade: Mike Boddicker for Curt Schilling and Brady Anderson

A lot of hindsight is needed for this trade to make the list. On July 29, 1988, pitcher Mike Boddicker came over in a trade with the Baltimore Orioles. The Red Sox would send them Brady Anderson and Curt Schilling. Wow!

Boddicker was a pretty good pitcher for the Red Sox with the biggest exception being his disastrous start in the ALCS against the Oakland Athletics. He allowed 6 earned runs, 3 home runs, and lasted just 2.2 innings. He was much better in his 1990 start, again versus Oakland, but came away as the loser again.

His regular season success of going 39-22 with a 3.49 ERA was definitely overshadowed by his October starts. When the Red Sox needed him most, Boddicker didn’t deliver.

Meanwhile, the Orioles ended up with a very good outfielder for more than a decade when they acquired Anderson. His greatest claim to fame was hitting 50 home runs out of nowhere in 1996. Even aside from that he was a base stealing threat in the early 1990s and a well-rounded hitter who reached base at a .364 clip for the Orioles.

Easily the most fascinating part of this trade was the presence of Schilling. No one knew at the time he’d become a Red Sox postseason hero. Traded by the Red Sox before actually playing a game for them, this is a case of wondering what those early Boston teams would have looked like if a different pitcher had been traded. Schilling didn’t start to have major league success as a starter until 1992 when he first joined the Philadelphia Phillies.

A seemingly necessary trade for Boston without the payoff, the history of this franchise would have looked much different with Anderson and Schilling on the roster throughout the 1990s.

6) Worst Red Sox trade: Jon Lester and Johnny Gomes for Yoenis Cespedes

This was certainly a curious move by both teams involved. On July 31, 2014, Boston sent pitcher Jon Lester, outfielder Jonny Gomes, and cash to the Oakland Athletics for Yoenis Cespedes plus a compensatory draft pick.

Lester was a Red Sox hero but the time to trade him away before he hit free agency had come. He ended up being the right man for Oakland in their 2014 postseason chase. Lester would go on to finish his career with exactly 200 victories with the final one coming in 2021 with the St. Louis Cardinals.

How Lester and Gomes performed didn’t really factor into what made this a bad deal for the Red Sox. What made this a failure was how little Cespedes contributed.

Cespedes batted .269/.296/.423 for the Red Sox in 2014 and would make his way to the Detroit Tigers in the offseason when Boston swapped him, Gabe Speier, and Alex Wilson for pitcher Rick Porcello. Porcello was a dud in his first season with the Red Sox, going 9-15 with a 4.92 ERA. He did manage to win the 2016 Cy Young Award in an amazing outlier season in Boston. His overall Red Sox totals include a 73-55 record and 4.43 ERA.

It seems like the Red Sox could have done a lot more when they traded Lester away than to acquire an outfielder they disposed of quickly. It’s not epically bad, however, it does seem like the assets could have been used much better.

5) Worst Red Sox trade: Tris Speaker to the Indians

Tris Speaker began his career with the Red Sox and even took home the MVP in 1912 back when players could win the award only once in their career. He was an early Boston sports legend who would go on to have 3514 career hits. Among them were a major league record 792 doubles.

On April 9, 1916, the Red Sox called or telegrammed or sent a Morse code message to the Cleveland Indians to make a trade. Cleveland would acquire Speaker in exchange for Sad Sam Jones, Fred Thomas, and $55,000.

As superb as Speaker was for Boston, he was even better in Cleveland. His first year assured fans it was the right trade to make. He led the league with 211 hits and a .386 batting average. He’d continue to pummel baseballs in Cleveland for 11 seasons.

Jones would join the Red Sox pitching staff for six seasons where he put up just okay numbers, finishing with a 64-59 record and 3.39 ERA. Thomas spent only one year in Boston before getting purchased away by the Philadelphia Athletics. He didn’t do much while in a Red Sox uniform either.

This trade is probably much worse than we give it credit for. The only thing many of us associate Speaker with is the Hall of Fame. At least he wasn’t sent to the Yankees.

4) Worst Red Sox trade: Sparky Lyle to the Yankees

Any trade involving the Red Sox and New York Yankees is bound to go down in history as a memorable one. On March 22, 1972, the two longtime rivals made a deal that would turn out to be one of the worst the Red Sox could ever make.

Sparky Lyle was a very good reliever for the Red Sox in the late 1960s and into the early 1970s. At 22-17 with a 2.85 ERA out of the bullpen, he was one of the pitchers who helped increase the importance of bullpens. Specifically, he was a founding father of the closer role.

Lyle would turn up the heat immediately upon joining the Yankees. Over the course of seven seasons, Lyle was 57-40 with a 2.41 ERA. He saved 141 games for New York and captured the 1977 American League Cy Young Award.

To land Lyle, the Yankees gave up two players. Danny Carter was an aging first baseman who would hit .262/.301/.384 for the Red Sox in three seasons. He never played more than 100 games for them in any of those years. Mario Guerrero was much less productive. He batted .241/.278/.278 for the Red Sox in his two years. He never once hit a home run in any of his 537 plate appearances.

This is an all-time bad Red Sox trade made even worse by where he ended up.

3) Worst Red Sox trade: Mookie Betts to the Dodgers

It’s not too soon to declare this trade a disaster. Trading Mookie Betts to the Los Angeles Dodgers is fresh in everyone’s minds. Rather than look to extend the star outfielder prior to reaching free agency, the Red Sox unloaded him and David Price in a deal to Los Angeles.

Betts has been exactly as advertised as a member of the Dodgers. There is no need to go into specific numbers. While not quite up to par with his Red Sox performance, who wouldn’t want him in Boston for life?

The badness of trades requires a little more than what the star accomplishes. Aside from playing well and helping the Dodgers win the 2020 World Series, this trade looks horrible for Boston for what they got back.

Jeter Downs, Connor Wong, and Alex Verdugo is the package of players the Red Sox received from the Dodgers in this move. Downs is already gone following a December 2022 waiver claim. Wong has some hope left in him but the clock is ticking on him ever being more than a backup or platoon catcher. Then there’s Verdugo who has played well for Boston but nowhere near the same scale as Betts.

The Betts trade does have some shades of the blockbuster that sent Carl Crawford and others to the Dodgers in a salary dump. The difference is the Red Sox won the World Series a year later. Since Betts left, they haven’t had the same luck.

2) Worst Red Sox trade: Jeff Bagwell for Larry Andersen

Only two years after he was drafted in the first round by the Red Sox, Jeff Bagwell was the Rookie of the Year. There’s a problem. He didn’t do it for Boston. Bagwell won his 1991 Rookie of the Year with the only major league team he would ever play for, the Houston Astros.

The 1994 MVP would finish his career with 2314 hits and 449 strikeouts on his way to eventually landing in Cooperstown. The Red Sox had him all the way up until August 30, 1990, when they traded him to Houston for reliever Larry Andersen.

Andersen was a quirky reliever during his playing days and has even carried over his fun personality to Philadelphia Phillies broadcasts. This hardly helps make up for the fact that the Red Sox traded a star like Bagwell to Houston for a middle reliever.

To ease the pain a little bit, Andersen was terrific for the Red Sox in his 22 regular season games. He pitched to a 1.23 ERA in 1990 after joining them. Unfortunately, he got knocked around in the ALCS with a pair of earned runs in 3 innings. He was the loser in Game 1 of the ALCS when he allowed two late runs to the Oakland Athletics right before the wheels completely fell off for the Red Sox.

1) Worst Red Sox trade: Babe Ruth for $100,000 to the Yankees

Not all trades are built the same. For instance, there is this trade. It might be the most famous in the sport. On December 26, 1919, Red Sox fans had their Christmas ruined when Babe Ruth was sold to the New York Yankees for $100,000. Even with inflation factored in, this was a horrendous move for the Red Sox. It’s one that lives on today.

Ruth was already a two-way star. He led the American League in home runs in 1918 and 1919. This was the beginning of his transition away from mostly pitching. Ruth was about to embark on the journey to becoming the first megastar in Major League Baseball history.

The Yankees immediately moved Ruth to the outfield where he’d mash 54 home runs in 1920. The decade belonged to him. While flappers danced excitedly and unaware of the Great Depression that lay ahead, Ruth and his toothpick legs made their way around the bases more than anyone else and by a wide margin.

The trade completely shifted the power in baseball. Ruth won World Series with the Red Sox in 1915, 1916, and 1918. Baseball was now a Yankees sport. He’d win four more with them. It began the “Curse of the Bambino” and a championship drought for the Red Sox that wouldn’t end until 2004. This trade gets the blame.