5 worst free-agent contracts in Boston Red Sox history
By Sean Penney
Lackey left the Red Sox rotation lacking
The Red Sox signed John Lackey to a five-year, $82.5 million deal prior to the 2010 season. The idea was to form a dominant trio at the top of the rotation alongside Josh Beckett and Jon Lester but the plan didn’t pan out as well as expected.
Lackey spent the first eight seasons of his career with the Los Angeles Angels, notching 102 wins while posting a 3.81 ERA. He peaked in 2007 when he won 19 games with a league-leading 3.09 ERA to earn an All-Star appearance and a third-place finish on the AL Cy Young award ballot.
While he looked the part of an ace during his prime years with the Angels, he performed more like a back of the rotation starter when he arrived in Boston. In 2010, Lackey went 14-11 with an underwhelming 4.40 ERA and a 6.5 K/9 that was his lowest strikeout rate since he was a rookie.
He followed that with a miserable season in which he produced a career-worst 6.41 ERA, led the league with 114 earned runs, and saw his strikeout rate dip to 6.1 K/9 while his walks increased to a career-worst 3.2 BB/9. Lackey’s struggles contributed to Boston’s historic collapse that season and he was a member of the infamous Chicken & Beer club that embarrassed the organization.
Tommy John surgery wiped out Lackey’s third season in Boston but he bounced back strong in 2013. Despite a losing record (10-13), Lackey produced a 3.52 ERA, 7.7 K/9 and 1.9 BB/9 that was more in line with what the Red Sox were expecting when they signed him. He was solid in the postseason, helping the Red Sox capture a World Series title.
Lackey had a unique clause in his contract that included a 2015 team option at the minimum salary if the righty missed significant time to a pre-existing elbow injury, which is what led to him undergoing Tommy John surgery. Getting Lackey for a bargain price for an extra year would have helped offset the first three miserable seasons he spent in Boston, especially since he was pitching well again post-surgery. Unfortunately, Lackey made it clear that he wasn’t interested in pitching for a minimum salary. There were rumors that he would threaten to retire if Boston tried to hold him to that commitment.
The Red Sox needed to hit the reset button following a disappointing start to the 2014 season. Rather than risk an ugly confrontation with Lackey over his contract, Boston dealt him to the St. Louis Cardinals at the trade deadline for Allen Craig and Joe Kelly.
Craig was an All-Star in 2013 and made a strong impression during St. Louis’ World Series loss to Boston but he was never the same after a foot injury derailed his career. He hit a pitiful .139 with a .432 OPS in 65 games over two seasons with the Red Sox until he was mercifully released.
Kelly had his moments in Boston and established himself as a fan-favorite but he failed to deliver as the starting pitcher they hoped would replace Lackey. He found his groove when he moved to the bullpen but wasn’t quite as valuable in that middle relief role.
Meanwhile, Lackey agreed to play for the Cardinals under the same minimum contract he supposedly refused to honor in Boston. He had an excellent year in St. Louis, going 13-10 with a 2.77 ERA.
Lackey was a poor free-agent signing due to being unproductive or injured for the first three years of the deal. He doubled-down on making the signing a poor decision by essentially forcing a trade that stuck the Red Sox with Allen’s horrible contract.