Ranking the Worst Trade Deadline Deals in Red Sox History

It's still not clear whether or not the Red Sox will be buyers or sellers at the trade deadline this year, but they've definitely had their fair share of summers where they found themselves squarely in one category or another, whether they botched it or not.

And though the Andrew Cashner trade might feel like a mistake, the Sox have had far worse deals. Here are the worst deadline moves in Red Sox history.

3. SP John Lackey for SP Joe Kelly and OF Allen Craig

In the summer of 2014, fresh off of a World Series victory over the Cardinals, the Red Sox found themselves as sellers at the deadline. They shipped out Game 6 starter John Lackey to that same team from St. Louis in exchange for Joe Kelly and Allen Craig. Lackey went on to post a 3.10 ERA in his 43 starts with St. Louis (and made $500,000 the following season) before winning his third World Series with the Cubs in 2016. Joe Kelly, meanwhile, gave the Red Sox exactly one season in which he managed an ERA below 4.00, and Allen Craig slashed .139/.236/.197 in just 195 plate appearances with the team.

2. SP Jon Lester and OF Jonny Gomes for OF Yoenis Cespedes

2014 was really not a fun year for the Red Sox. In addition to the Lackey deal, the team also shipped fan-favorite starter Jon Lester, who was in a contract year, and Jonny Gomes to the Oakland Athletics in exchange for Yoenis Cespedes. Contract negotiations between Boston and Lester had stalled, and it seemed unlikely that he'd be pitching in a Red Sox uniform in 2015. Lester signed with the Cubs in the offseason and won the World Series alongside Lackey in 2016. Cespedes, on the other hand, spent all of two months in Boston, posting a .719 OPS before he was traded to the Tigers in the offseason in exchange for Rick Porcello.

1. SP Curt Schilling and OF Brady Anderson for SP Mike Boddicker

The Red Sox were in need of some proven rotation help back in 1988, so they brought in Mike Boddicker from the Orioles in exchange for Curt Schilling and Brady Anderson. Boddicker was everything the team could have asked for that year, posting a 2.63 ERA in 14 starts, but he put up a stinker in the ALCS, allowing six runs in less than three innings. Schilling, meanwhile, posted a 3.33 ERA across 15 seasons with four separate teams from 1988 to 2003, winning the World Series with the Diamondbacks before finishing his career in Boston. Anderson turned out to be a three-time All-Star with the Orioles, putting up a 50-home run season in 1996. Even though Schilling ultimately helped them break the curse, this is unequivocally the worst deadline deal in Red Sox history.