10 worst Boston Red Sox trades in team history

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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.