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Ranking every Boston Red Sox season from this decade

By Sean Penney

SEATTLE, WA - MARCH 28: Chris Sale #41 of the Boston Red Sox pitches against the Seattle Mariners in the first inning during their Opening Day game at T-Mobile Park on March 28, 2019 in Seattle, Washington. (Photo by Abbie Parr/Getty Images)
SEATTLE, WA - MARCH 28: Chris Sale #41 of the Boston Red Sox pitches against the Seattle Mariners in the first inning during their Opening Day game at T-Mobile Park on March 28, 2019 in Seattle, Washington. (Photo by Abbie Parr/Getty Images) /
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BOSTON, MA – JULY 20: Jon Lester #31 of the Boston Red Sox throws in the first inning against the Kansas City Royals at Fenway Park on July 20, 2014 in Boston, Massachusetts. (Photo by Jim Rogash/Getty Images)
BOSTON, MA – JULY 20: Jon Lester #31 of the Boston Red Sox throws in the first inning against the Kansas City Royals at Fenway Park on July 20, 2014 in Boston, Massachusetts. (Photo by Jim Rogash/Getty Images) /

2014

The reigning World Series champions did a miserable job of defending their title in 2014. The Red Sox sputtered out to a 13-14 start in April. Their mediocrity quickly put them in a hole that they never managed to climb out of.

This season was overshadowed by the failed contract negotiations with ace Jon Lester. The Red Sox approached the lefty with a low-ball offer following his remarkable postseason run in 2013. Lester quickly cut off negotiations, blindsiding an ownership group that assumed they would receive a counter-offer so that the sides could meet in the middle.

When the Red Sox reached the trade deadline out of the playoff hunt, Lester was shipped to the Oakland A’s for Yoenis Cespedes. Boston gambled that they could get an asset for their ace, then turn around and sign him in free agency that winter. They were proven wrong when the Chicago Cubs outbid them, leaving fans stunned that the organization had botched their relationship with the homegrown star pitcher.

One of the few silver linings from this season is that 2014 saw the major league debut of Mookie Betts. It was only a 52-game sample but the future superstar flashed his potential to foreshadow what was to come.

Boston ended this lost season with 71 wins and a last-place finish in the AL East. The Red Sox pulled off the rare misfortune of going from worst-to-first then back to worst again.

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