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.