2011
This was hardly the worst season of the decade in terms of the win column but 2011 was easily the most heart-breaking.
The Red Sox were one of the best teams in baseball through the first five months of the season but ran out of steam down the stretch amid a rampant string of injuries to the starting rotation. Boston posted a dismal 7-20 record in September to become the first team in major league history to miss the playoffs after holding a nine-game lead entering the final month of the season.
All they needed to do was beat the lowly Baltimore Orioles on the final day of the season to clinch a Wild Card berth but Jonathan Papelbon‘s blown save cost them that opportunity. Moments later, the Tampa Bay Rays rallied to beat the New York Yankees to steal Boston’s playoff spot.
The epic September collapse brought on controversy from rumors of an undisciplined clubhouse. Josh Beckett was the ringleader of a pitching staff that spent their off days drinking beer and eating fried chicken in the clubhouse. The lackadaisical attitude was viewed as one of the reasons for the collapse and manager Terry Francona took the blame for losing control of his players, leading to his exit at the end of the season.
The bright spot of this season was a career year from Jacoby Ellsbury. He hit .321 with 32 home runs to finish as the runner-up in the AL MVP race. It was the first and only year that Ellsbury was an All-Star, Silver Slugger and Gold Glove winner.
Boston won 90 games that season but missing the playoffs due to the worst late-season collapse in major league history, plus the clubhouse turmoil, left a sour taste in the mouths of Red Sox fans.