Even 100 years and four World Series titles haven’t been able to completely erase the Boston Red Sox's association with bad trades.
The franchise’s identity has been molded to reflect these failures. From the “Cardiac Kids” to the “Idiots,” the players themselves have adopted monikers that imply impending doom, and the fans sometimes masochistically identify as “losers.” Who can blame them considering Boston’s heartbreaking history?
Such a painful past has even colored the way Red Sox fans approach the news of trades. Even upon the announcement of the blockbuster deal for Garrett Crochet this week, some met the news with, perhaps undeserved, skepticism. With that in mind, let’s open a few old wounds and remind ourselves of the beautiful pain with the worst trades of Red Sox history.
5 trades the Boston Red Sox likely wish they could do over
The one that started it all: Babe Ruth
Gallons of ink have been spilled over the 1919 trade that started the Curse, but to overlook this trade would be a disservice to the Red Sox and to Babe Ruth himself.
After all, the Bambino won almost as many World Series in Boston as he did in New York. In fact, his championship track record was better in Beantown as the Red Sox went 3-0 in the Fall Classic with Ruth while the Yankees went 4-3 in their seven World Series with the slugger. Statistically speaking, his pitching provided more championship-worthy benefits to the Red Sox than his hitting did for the Yankees: he posted a 49.3% cWPA in his three pitching outings for Boston and a 43.1% cWPA over his 118 World Series at-bats with New York.
Of course, this trade is less about what Ruth gave to the Sox than what owner Harry Frazee got in return from the Yankees: $100,000 and a loan for the Fenway Park mortgage. In some ways, Frazee dodged a bullet. The other offer on the table would have brought $60,000 and Shoeless Joe Jackson to Boston. Jackson, of course, would be banned from baseball after the 1920 season.
Even though Ruth performed slightly worse against the Red Sox than his career marks, seeing the greatest slugger of all time suited up in pinstripes has haunted the franchise for years. No amount of goodwill extended by Ruth throughout the years could ever repair the broken relationship with Red Sox Nation.
Boston trades one of the greatest outfielders of all time, Tris Speaker
Like the Ruth trade that would follow, Tris Speaker’s unceremonious departure in 1916 stemmed from a contract dispute. Unlike Ruth, Speaker proposed a partial pay cut from his $12,000 salary in an attempt to mollify Red Sox president Joseph Lannin. Speaker and Lannin could not agree on the terms with the former asking for a $3,000 cut while the latter asked for $6,000.
As a result, Speaker, the MVP just four years prior, was shipped off to Cleveland, where he led the Majors in most offensive categories including batting average, hits, and OBP. The center fielder also continued his defensive dominance and remains the all-time leader at the position in assists and double plays. Some still contend that Speaker is among the best center fielders of all time, and he gave Nap LaJoie a run for his money as the greatest Cleveland player in history.
If losing a future Hall of Famer weren’t enough, the return to the Red Sox was paltry. Sad Sam Jones, a wiry righty, experienced some success over his six seasons in Boston, winning 23 games as the ace in 1921. Fred Thomas, the other player sent by Cleveland, played a mere 44 games with the Sox in 1918.
The $50,000 that exchanged hands during the Speaker trade may have been the biggest boon to Boston. Following the 1917 season, the Red Sox used some of their financial flexibility to acquire Bullet Joe Bush, Wally Schang, and Amos Strunk from the Philadelphia A’s.
Bush and Schang were instrumental in Boston’s 1918 World Series win over the Cubs. Bush relieved Ruth with runners on first and second in Game 4 and induced a sacrifice bunt and a game-ending double play to preserve the 3-2 Red Sox win. The performance was statistically the second-most consequential moment in the series. Schang, for his part, broke a scoreless tie with an RBI single in the fourth inning of Game 3. The Red Sox went on to win, 2-1.
However, the fleeting joy of a championship did little to dull the pain when Speaker won a World Series with the Indians in 1920 and demolished Red Sox pitching for the next 11 years. He had a career slugging percentage of .521 against his former club and struck out just 19 times in more than 1,000 plate appearances.
Native son Jeff Bagwell becomes the face of Houston
Jeff Bagwell, a lifelong Red Sox fan, was living the dream when Boston selected him in the fourth round of the 1989 MLB Draft. In his first full season of pro ball in 1990, he thrived with the New Britain Red Sox, who played 15 miles or so from his former high school in Middletown, Connecticut. At the trade deadline that year, though, the Red Sox sent him to Houston for reliever Larry Andersen.
The move made logical sense for Boston at the time. Bagwell was blocked at third base by Wade Boggs, who was winding down the best stretch of his illustrious career, and the Red Sox were in need of high-leverage pitchers for the postseason race; Boston’s relievers had allowed opponents a .319/.390/.464 slash line in July, but the team had climbed from a game back in the division to 6.5 games up on August 30.
Andersen, a 37-year-old reliever, brought postseason experience and a string of productive years to Boston. He had a 2.57 ERA over parts of five seasons with Houston and had a 1.95 ERA when he was traded. Andersen undoubtedly aided Boston’s quest for the division title, as he allowed just three runs over his 15 regular-season games. Unfortunately, he flopped in the postseason for Boston and was outdueled by former Red Sox righty Dennis Eckersley in the ALCS against Oakland. Andersen left the team via free agency after the season.
Bagwell, of course, went on to have a Hall of Fame career as a member of Houston’s “Killer B’s,” racking up a Rookie of the Year, MVP, Gold Glove, and three Silver Sluggers. The Red Sox instead put their faith in Mo Vaughn, who picked up an MVP Award of his own in 1995, but the mid-90s Boston teams would have greatly benefited from Bagwell.
Youth over experience brings Yoenis Cespedes to Boston
In 2014, Yoenis Cespedes was a promising young star with an All-Star nod, a top-10 MVP finish, and a Rookie of the Year runner-up under his belt. Jon Lester was fresh off his heroic World Series performance in which he held the Cardinals to just one run over 15 ⅓ innings. The 2014 Sox, though, were floundering so general manager Ben Cherington made the swap, including left fielder Jonny Gomes in the deal.
Cespedes arrived with an unsavory .303 on-base percentage, and things got worse from there. The prodigious power that gained him acclaim in Oakland abandoned him in Boston, and he hit just five homers over the final 51 games of the season. The Red Sox completed their first-to-worst slide, finishing 20 games below .500. Red Sox fans had to sit at home and watch Lester lead the A’s to the postseason, although he coughed up six runs in the AL Wild Card Game against the Royals.
A silver lining appeared in the 2014 offseason when the Red Sox flipped Cespedes to the Tigers for Rick Porcello, who won a Cy Young and a World Series with Boston. Ultimately, the Cespedes deal could be seen as a plus in the long run thanks to Porcello’s contributions. The Red Sox also escaped the Cespedes megadeal which saw the Mets pay him almost $100 million for five injury-prone seasons.
Lester, on the other hand, enjoyed a strong second act with the Cubs. He earned NLCS MVP honors as Chicago marched its way to their own curse-breaking World Series title. The following year, Lester was the runner-up for the NL Cy Young Award.
Gomes, whose go-ahead three-run homer in Game 4 of the 2013 World Series made him an instant Red Sox hero, struggled after the trade. Bouncing from the A’s to the Braves and the Royals before retiring after the 2015 season.
Mookie Betts heads West
Mookie Betts’ mounting accolades all but guaranteed him a huge payday as he neared free agency, and the Red Sox wanted relief from the Competitive Balance Tax. Still, seeing the 2018 MVP suit up in Dodger Blue broke the hearts of Red Sox Nation. David Price also figured in the deal that brought Alex Verdugo, Jeter Downs, and Connor Wong to Boston.
Price, who was the staff workhorse and won two games in the 2018 World Series against the Dodgers, had little success in Los Angeles. After the trade, he sat out the 2020 season due to the COVID-19 pandemic, missing out on the Dodgers’ championship run.
Verdugo became a mainstay in the Red Sox lineup but in no way made up for the loss of Betts. Downs, then a promising prospect, struggled to adjust to high-level pitching and now plays in Japan. Wong is the last remaining piece in Boston, where he has filled a valuable catching and utility role.
The Red Sox have not been competitive since bidding Betts goodbye. Meanwhile, the Dodgers have made the postseason in each of the past five seasons, winning two championships. Given the differing trajectories of these storied franchises, we may be looking back at this deal as a new Curse of the Betts-bino.