Boston Red Sox ace Jon Lester’s contract is up at the end of the year, and talks between the front office and Lester have led nowhere. Halfway through the year, the southpaw remains unsigned for the long-term, infuriating Red Sox fans with every passing day. This growing anger is justifiable. I mean, this is a guy who’s postseason success and imposing repertoire forges him into one of the game’s elites. He has, however, encountered his fair share of struggles the past few years, making Boston’s hesitation somewhat understandable. So, if Ben Cherington and Company aren’t going to give him the money he desires, then trading him is very sensible.
Despite Boston’s little winning-streak, the Red Sox probably aren’t postseason-bound, and, essentially, Lester’s services will be useless. Yet, if they are serious, you must keep him for the second-half. If not, the BoSox and Lester’s relationship will be strained, and the chances they reach a long-term agreement is next to nil.
The Red Sox have two smart options, and quite frankly it’s really as simple as that. Lester likely yearns a deal parallel to the seven-year, $153 million pact Cole Hamels received from the Philadelphia Phillies; maybe even more considering he’s having a career year in ’14 with a 2.65 ERA and 2.61 FIP. If that’s too expensive, and Boston is confident with the plethora of pitching prospects in the farm, then deal him and get something back. If they aren’t, keep him for the rest of the year and try hard after the season has concluded to re-sign the stellar left-handed pitcher.