Red Sox's $135 million offer to Lester falls short
Click here to access our MLB Tracker, which includes every offseason rumor, trade and signing.
The Boston Red Sox didn't lose Jon Lester late Tuesday night, he was gone back in April after scoffing at the team's initial extension offer.
Boston lowballed the left-hander with a contract that proved to be well below market value – between $70 and $80 million. Lester tabled negotiations until the offseason and the Red Sox cost themselves an opportunity at exclusive negotiation rights.
Chicago Cubs president and former Red Sox general manager Theo Epstein smelled blood. Once Lester hit the open market, Epstein was aggressive and used his former relationship with the pitcher as leverage over his predecessor in Beantown, Ben Cherington, while the pair of 40 and under executives tried to outdo one another.
The two jilted former members of the Red Sox organization had the opportunity to take a parting shot at the club they unceremoniously left – and they didn't pass up the opportunity.
Epstein knew Lester, knew his family and knew how to land arguably the biggest free agent on the market. When he finally netted Lester with a monster six-year, $155-million deal, one that was head and shoulders over the Red Sox reported $135-million offer, Epstein acquired a cornerstone piece for a franchise trying to end an over century-long World Series drought. Boston was even out bid by the San Francisco Giants, a team that Lester eliminated from contention before making his final decision.
(Related: Cubs pay Lester record-setting sum for chance to win now)
With a chance to redeem themselves after initially lowballing Lester, the Red Sox second chance fell well below market value once again. Principal owner John Henry even flew to meet Lester at his home in Atlanta and the team was still outbid by $20 million.
If there is a silver lining for the pitching starved Red Sox, it's that they didn't lose Lester for nothing. With negotiations sidelined, the team opted to trade the three-time All-Star to the Oakland Athletics last season for outfielder Yoenis Cespedes, who remains under contract in 2015.
The Red Sox could have opted to hold on to Lester, issue a qualifying offer and collect a draft pick as compensation, but with the team built to win in 2015, a controllable player was much more desirable.
With a loaded outfield, Cespedes's time in Boston could last just 51 meaningless games in a lost 2014 season, but his impact on next year's roster could be much greater.
Should the Red Sox flip Cespedes for a much needed pitcher, it softens some of the blow on striking out with Lester. It is reported Boston has already had discussions regarding a swap of the Cuban outfielder for the likes of Ian Kennedy of the San Diego Padres or Rick Porcello of the Detroit Tigers.
While none of those arms bring what Lester would have, it's a nice consolation and an inevitable result of their own doing. However, the loss of Lester will likely hurt the Fenway Faithful for years to come.