Red Sox blow Wild Card in September 2011
Again, it’s hard to justify putting anything post-2004 on this list, but if there’s one moment (or series of moments) that deserves to be on here from the last twenty years, it’s this one. The Sox looked to avenge their third place finish in 2010 by reloading and spending a ton of money in the offseason.
They traded for Adrian Gonzalez and signed free agent Carl Crawford. On paper the team looked absolutely loaded and there were numerous headlines both in New England and the national media calling the 2011 one of the best teams ever, before they’d even played a single game.
The season didn’t go quite that well, but the Sox were still firmly in control of their destiny. The division looked out of reach thanks to the New York Yankees, but the Red Sox seemed to have a stranglehold on the Wild Card. Heading into September, the Sox had a nine game lead in the Wild Card over the Tampa Bay Rays.
As the Rays continued to play great baseball, the Red Sox utterly collapsed, going 7-27 during the month including a horrific blown save in the ninth inning of their final game of the season in Baltimore. The coup de grace was a failed diving catch by Crawford (who had an abysmal season) which allowed the winning run to score for the Orioles.
The fallout from the collapse was just as bad. Manager Terry Francona was let go and smeared by the team on the way out, GM Theo Epstein left to join the Chicago Cubs, and Jon Lester, Josh Beckett, and John Lackey were exposed as having been playing video games, eating fried chicken, and drinking beer in the clubhouse during games.
It was an incredibly ugly end to a tumultuous season and would lead to the Red Sox most recent nadir in 2012 when they hired the insufferable Bobby Valentine to manage the team. The 2012 Red Sox had the franchise’s worst season since 1966 and had so many character issues on the roster that the team underwent a massive housecleaning which led to the glorious 2013 season.