Jon Lester and Jonny Gomes for Yoenis Cespedes – 2014
After winning the World Series in 2013, the Red Sox found themselves as sellers at the deadline the following season. Jon Lester was in the middle of a career year with free agency looming, so when extension negotiations stagnated the front office decided to trade their ace to the Oakland Athletics for Yoenis Cespedes, who came with an extra year of control.
Many fans blame the low-ball $70 million offer the Red Sox insulted Lester with as the reason why he’s no longer in Boston, but that’s not entirely true. All that did was set contract talks aside until after the season, but it was the trade the ultimately cost the Red Sox their best pitcher.
Had he remained with the team through the rest of that season then Boston would have entered free agency as the heavy favorites to retain Lester. The previous regime wasn’t willing to go as far as the Chicago Cubs did for an over-30 starter, but all they had to do was give him an offer in the same ballpark. Lester had indicated a willingness to take a hometown discount to remain in Boston, but that went out the window after he was traded. By his own admission, leaving Boston to sign as a free agent elsewhere would have been very difficult for him to do, but this trade gave Lester the opportunity to experience another city for the first time in his career. Deciding not to return after being traded turned out to be easier than bolting as a free agent would have been if he hadn’t already left.
The trade itself brought back what seemed like relatively fair value at the time, as Cespedes gave them an All-Star caliber power-hitting outfielder, but it didn’t take long for buyer’s remorse to set in. Cespedes hit only 5 home runs in 51 games for the Red Sox, while posting a sub-.300 on-base percentage. The cannon of an arm he’s known for was wasted playing in Fenway Park’s shallow left field and he made a habit of mental lapses on defense that overshadowed his natural abilities.
It only took two months for the Red Sox to tire of Cespedes, who they traded in the offseason to the Detroit Tigers for Rick Porcello. That deal appeared to be in danger of becoming among the worst in franchise history as well after a disastrous 2015 season for Porcello, but he’s turned his career around this year. Porcello is clearly no Lester, but he is tied for the league lead in wins while posting a 3.47 ERA reminiscent of a typical Lester season when he was here.
Porcello’s career year doesn’t make up for the Lester trade, but it at least mitigates the damage when you consider the Red Sox likely wouldn’t have him in the rotation if they hadn’t dealt Lester for the chip that brought Porcello to Boston. That’s the only reason why the Lester deal isn’t higher than the next ill-fated trade on this list…