Boston Red Sox: Remembering the worst trades in franchise history

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Bronx, NY – JUNE 12: Infielder Jeff Bagwell #5 of the Houston Astros at bat against the New York Yankees during the interleague game on June 12, 2003 at Yankee Stadium in Bronx, New York. The Yankees defeated the Astros 6-5. (Photo by Al Bello/Getty Images) /

The Boston Red Sox have made countless shrewd deals over their long and storied history. Here’s a look at some of the worst trades they’ve ever made.

The history of the Boston Red Sox is filled with great players who thrilled the Fenway Faithful with their exploits on the baseball field. Many of the greatest Red Sox legends spent the entirety (or close to it) of their careers in Boston and became legends after their playing days were over.

However, like any franchise that’s been around as long as they have (especially over a hundred years), their history is also littered with great players they traded away. Sometimes these deals worked out, but often they ended up hurting the Red Sox and in many cases, the damage lasted for years.

The list that follows takes a look at what I think are some of the worst trades the Red Sox have made in franchise history. Some of these deals ended up being one-sided in favor of the teams on the other end, and some benefited the Red Sox but still ended up being failures for various other reasons. All impacted the Red Sox negatively to some degree or other.

Presented in (mostly) chronological order, let’s begin!

Babe Ruth

This is the biggest one in Red Sox history and whether or not you believe in curses, it was the capstone on a series of bad decisions which hampered the Red Sox for decades. Everyone knows that after winning the World Series in 1918, the Red Sox sold Babe Ruth to the Yankees after the 1919 season and they didn’t win another title until 2004.

Ruth spent the beginning of his career, from 1914-1919, with the Red Sox and was one of the best pitchers in the American League in helping them win three World Series (1915, 1916, 1918).

He was also starting to develop into the power hitter that he’d become in the 1920s and 1930s. However, as Ruth got better and better, he started to realize the three-year, $27,000 contract he signed in 1919 was less than he was worth.

In a stunning move that to this day beggars belief, then-Red Sox owner Harry Frazee sold Babe Ruth and his contract to the Yankees for roughly $100,000. The owner was deep in debt from his purchase of the team and also, as a theater buff, was looking to finance a production of the Broadway musical “No, No Nanette.” In a nutshell, he needed cash and he needed it fast.

The transaction completely altered the fortunes of both franchises for decades to come. The Yankees instantly became contenders as Ruth single-handedly revolutionized power hitting and ushered in the live-ball era in baseball.

He’d go on to lead the Yankees to seven pennants and four World Series victories during his fourteen years in New York and became an American cultural icon whose presence still looms large to this day.

As for the Red Sox, they immediately sank into the American League basement and wouldn’t finish above .500 again until 1934. They didn’t win another pennant until 1946 and didn’t win a World Series until 2004.

While it was Ruth’s hitting exploits in New York that made him the legend he still is today, in his six Boston seasons he hit .289 with 49 home runs and 224 RBI. He also went 89-46 with a 2.55 ERA and 483 strikeouts on the mound.

Ruth was on pace to be a Hall of Fame pitcher when the Red Sox traded him. Instead, he went on to become the greatest slugger in the history of the game and one of baseball’s biggest icons. The fact that he did it for the Red Sox’s most bitter rival still makes it a bitter pill to swallow even after all these years.

Tris Speaker

Tris Speaker was the Red Sox biggest star before Babe Ruth, one of the finest offensive and defensive center fielders of his era. He was the centerpiece of the Red Sox “Million-Dollar Outfield” from 1910-1915 alongside Harry Hooper and Duffy Lewis. While he played during the waning years of the dead-ball era, Speaker was one of the best power hitters of his time.

In his nine seasons with the Red Sox, Speaker put up a .309 average with 39 home runs and 542 RBI (remember, this was the dead-ball era). He also had 1327 hits, hit 241 doubles, and stole 267 bases. By the metrics of his day, he was a superstar. Speaker clashed with Sox president Joseph Lannin, who asked Speaker to take a pay cut from $15,000 to $9,000 after the 1915 season.

His rationale for this request was the dip in Speaker’s batting average which went from .338 to .322, which hardly seems worth demanding a 40% pay cut over! When Speaker countered with $12,000, Lannin traded him to the Cleveland Indians right at the start of the 1916 season. In return, Boston got Sad Sam Jones, Fred Thomas, and some cash.

Speaker went on to win another World Series in Cleveland in 1920 while the Red Sox won two more in 1916 and 1918. Even after the trade/sale of Ruth to the Yankees, many Red Sox fans considered this, the Speaker deal, as the worst trade in team history. Many think that trading Speaker did more damage to the Red Sox than trading Ruth in 1920.

While the Babe was an excellent pitcher and was starting to show power at the plate, no one back then could have in their wildest dreams imagined what kind of hitter he’d eventually turn into in New York. By contrast, Speaker was already a superstar and the best player on the Red Sox. It’s a pattern that sadly would be repeated again multiple times in baseball history, even by the Red Sox themselves.

Jeff Bagwell

This one is routinely pointed to as one of the worst trades in Red Sox history by fans and the media alike and for good reason. Jeff Bagwell went on to become one of the most prolific sluggers of his generation and ended up in Cooperstown after his career was finished. His career is always pointed to by Red Sox fans as what might have been.

Bagwell was born in Boston, raised in Connecticut, and grew up a Red Sox fan. He was drafted by the Red Sox in 1989 and was an up and coming player in their minor league system when he was traded to the Houston Astros. The Red Sox were in the midst of trying to win the AL East and make the postseason in 1990 and needed relief pitching.

They approached the Astros about Larry Andersen and in return were asked for Bagwell. Since he hadn’t hit too many home runs thus far in his career, they made the deal and came out on the wrong end of it. Andersen pitched decently for the one month he was on the Red Sox, but they were swept by the powerhouse Oakland A’s in the 1990 ALCS.

Andersen was a free agent at the end of the season and left for San Diego. Meanwhile, Bagwell spent his entire career in Houston, from 1991 to 2005 and ended his career with a .297 average, 449 home runs, 1529 RBI, an OBP of .408, a .948 OPS, 1517 R, and 1401 BB. He was inducted into the Baseball Hall of Fame in 2017.

In essence, the Red Sox traded Jeff Bagwell for one month of Larry Andersen, who appeared in 15 games with a 1.23 ERA and one save in 22 innings. Granted, it may not have been obvious that Bagwell was a future Hall of Famer, but he was a rising star in the farm system and was traded away for a month of a then-37-year-old reliever.

If this isn’t the worst trade the Red Sox have ever made, it’s close to it.

Jon Lester

The Jon Lester trade had a big impact on the Red Sox almost a decade later and also presaged what would eventually happen to Mookie Betts, but we’ll get to that in a bit. The big lefty came up through the Red Sox system and made his major league debut in 2006. He’d go on to be a durable member of the Sox rotation until 2014.

Lester’s story was extra special because of what he overcame. In 2006 he missed the last month and a half of the season due to being diagnosed with lymphoma. After undergoing treatment and successfully beating it into remission, Lester returned to the Red Sox in mid-2007. He ended up being a key contributor to the 2007 World Series champs and even won the clinching game of the series, which was also his first career postseason start.

Lester would go on to throw a no-hitter in 2008 and help the Red Sox win another World Series in 2013. However, when his free agency was approaching the Red Sox lowballed him with contract offers. Lester said in the press he’d be willing to take a hometown discount, but the Red Sox front office took the “discount” part of that statement too much to heart.

Instead, they traded him at the 2014 deadline to Oakland for Yoenis Cespedes. Lester finished the season in Oakland, rebuffed the Red Sox contract offer in free agency, and signed with the Chicago Cubs where he won another World Series in 2016. Cespedes hit fairly well in Boston, putting up a .259 average along with 5 home runs and 33 RBI. However, the Red Sox ended up trading him after the season to Detroit for Rick Porcello.

Lester in his Red Sox career went 110-54 with a 3.75 ERA and 1386 strikeouts. Losing Lester and the fan backlash around it led to the Red Sox outbidding themselves to sign David Price in 2015, a deal that would have a ripple effect a few years later.

BOSTON, MA – OCTOBER 25: Curt Schilling #38 of the Boston Red Sox pitches against the Colorado Rockies during the 2007 World Series GM 2 October 25, 2007 at Fenway Park in Boston, Massachusetts. The Red Sox won the Series 4-0. (Photo by Focus on Sport/Getty Images) /

Curt Schilling and Brady Anderson

Every Red Sox fan knows that their trade for Curt Schilling prior to the 2004 season was one of the main moves that helped the team finally win the World Series, but what a lot of them may not know is that the Red Sox had Schilling before. He was drafted by the Red Sox in 1986 and spent two years in their minor league system before being traded to Baltimore.

Along with Schilling, the Red Sox traded another prospect of theirs, Brady Anderson. In return, the team got pitcher Mike Boddicker. Boddicker actually pitched pretty well in his two and half seasons in Boston, going 7-3 in 1988, 15-11 in 1989, and 17-8 in 1990. Along the way he helped the Red Sox win the AL East in 1988 and 1990 where they were swept in the ALCS both times by Oakland.

Schilling went on to find success in Philadelphia, leading them to the World Series in 1993 and then in Arizona where he teamed up with Randy Johnson to help the Diamondbacks win it all in 2001. Brady Anderson enjoyed a fourteen-year career in Baltimore, hitting 210 home runs along the way (including a 50 home run season in 1996).

This trade wasn’t necessarily terrible in the sense that who the Red Sox got in return didn’t pan out. Boddicker was solid and helped the team win during his time in Boston. However, the two prospects the Sox gave up were better than what they got back. Luckily, they got a do-over with Schilling which helped them win two World Series in 2004 and 2007.

Adrian Gonzalez

For years, then-Red Sox GM Theo Epstein had lusted after San Diego Padres first baseman Adrian Gonzalez. With his sweet left-handed stroke and power, Gonzalez was putting up 30-40 home runs every year and had a swing that seemed tailor-made for Fenway Park.

After years of trying to pry him away from the Padres, Epstein was able to do so in the winter of 2010 when he sent a package of Red Sox prospects, including Anthony Rizzo, to San Diego for Gonzalez. For the first half of the 2011 season, it looked as though it paid off in spades as the Red Sox signed him to a seven-year extension and locked him up long-term.

The 2011 Red Sox were cruising and Adrian was mashing, hitting 22 home runs heading into the All-Star break. However, after participating in the home run derby at the Midsummer Classic, he only hit 5 homers the rest of the way and finished with 27 on the season to go along with a .338 average and 117 RBI.

After the Red Sox historic collapse in September 2011, his power outage continued in 2012 when he hit .300 with 15 home runs and 86 RBI in 123 games. It turned out that Gonzalez was also not a good clubhouse guy, being outed as a clubhouse lawyer and one of the players who undermined manager Terry Francona in 2011, which led to the skipper’s firing.

In August of 2012, Gonzalez was shipped out to the Dodgers along with Josh Beckett and Carl Crawford in a massive salary dump. A guy who the Red Sox couldn’t wait to get ended up being one they couldn’t wait to get rid of.

Even worse for Boston, Rizzo became a Gold Glove first baseman and All-Star for the Cubs, helping them win the 2016 World Series while hitting 218 home runs (and counting) along the way.

Tyler Thornburg

This trade wasn’t franchise-altering, but it was still a bad trade where the Red Sox got the completely wrong end of the deal. Travis Shaw was a Red Sox draft pick who worked his way through the minors and made his major league debut in 2015. In 2016 he beat out the Red Sox big (literally and figuratively) free agent signing Pablo Sandoval for the starting third baseman spot coming out of camp in 2016.

Shaw was a solid fielder who showed promising power at the plate and ended up hitting .251 with 29 home runs and 107 RBI in his two seasons with Boston. However, in the winter of 2016 then-President of Baseball Ops Dave Dombrowski traded Shaw to Milwaukee for reliever Tyler Thornburg. It was a curious move since, even though he’d pitched well for the Brewers, Thornburg came to Boston injured.

Thornburg started the 2017 season on the IL with a shoulder injury and was then diagnosed with thoracic outlet syndrome which caused him to miss the entire season. He finally made his Red Sox debut in July 2018 but was ineffective and inconsistent. For some reason (most likely to save face on the trade), they re-signed him to a one-year extension in 2019.

Thornburg was even worse in 2019, becoming known among Red Sox fans as “Alex Cora’s white flag” since he was only ever put into games when the Red Sox were losing by a lot. He was demoted to the minor leagues in June and released by the team in July.

Meanwhile, Shaw hit 31 home runs for the Brewers in 2017 and 32 in 2018 as he helped them come to within a hair’s breadth of the World Series in 2018.

As was stated above, this wasn’t a trade that hurt the Red Sox too much, but it is one that they completely and utterly lost.

Mookie Betts

You knew it was coming, didn’t you? While it’s still too early to make a final judgment on how badly the Red Sox lost on this trade, there’s no denying that they did lose. Mookie Betts had been the Red Sox right fielder from 2014-2019 and during that time blossomed into a true five-tool player, their best all-around homegrown guy since Carl Yastrzemski, and one of the top five players in the league.