John Lackey for Allen Craig and Joe Kelly – 2014
Losing John Lackey doesn’t hurt nearly as much as losing Lester did, but this trade ended up as the worse of the two given the return.
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Lackey bounced back from a lost 2012 season to become the pitcher the Red Sox had always hoped for, but his contract situation put the team in a position where they felt they had to deal him. A clause in his deal stipulated that if Lackey missed significant time with a pre-exiting medical concern, which he did, then a team option at the league minimum price would be tacked on for 2015. Lackey threatened to retire rather than honor this stipulation, but instead of calling his bluff the Red Sox opted to deal him to the St. Louis Cardinals.
Of course Lackey ended up pitching for the Cardinals in 2015 for the bargain price of $507,500 and had an outstanding season, which he parlayed into a lucrative new deal this year to join old friend Jon Lester in Chicago.
In return the Red Sox received Allen Craig and Joe Kelly, neither of whom have provided much value to the team, while each has spent significant time in the minors. Craig is being paid $20 million over the next two seasons despite having been moved off of the 40-man roster, while Kelly has been converted into a middle reliever after several failed attempts to stick in the rotation.