5 trades the Red Sox likely wish they could do over

Babe Ruth Warming Up 1919
Babe Ruth Warming Up 1919 | Transcendental Graphics/GettyImages
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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.

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