Future of Ben Cherington, Boston Red Sox in the Hands of Jon Lester

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Jul 25, 2014; St. Petersburg, FL, USA; Boston Red Sox starting pitcher Jon Lester (31) throws a pitch during the first inning against the Tampa Bay Rays at Tropicana Field. Mandatory Credit: Kim Klement-USA TODAY Sports

The Red Sox have had a number of chances to sign pitcher Jon Lester early in 2014. They could have signed him after the miraculous 2013 World Series, or during Spring Training or even during the season. But they did not, they took a gamble and now they are paying the price.

Right now they are one of the teams in the mix for the southpaw, and instead of having that bonafide ace in the starting rotation they are now bidding for one. Make no mistake about it, signing Jon Lester will bring the Red Sox right back to where they were at the beginning of last season which necessarily isn’t a bad thing. Jon Lester is one of the few bright spots of last year’s team, no one can look me straight in the face and say that the reason the 2014 Red Sox failed to make the playoffs was because of Jon Lester. So signing Jon Lester will be a HUGE move for the Red Sox and get them going in the right direction for 2015.

But if Lester decides to go elsewhere, it will be go as one of the worst moves in the Henry/Lucchino/Werner Era. Losing out on Jon Lester would spell doom for the 2015 Red Sox from the get-go, not having that established and trusted ace in your staff will hurt them there’s no question about that. Sure they could go after a guy like James Shields, or Cole Hamels but are you really going to sit back and tell me those guys are on the same level as Jon Lester? Lester has the track record of winning under the bright lights of Boston, and we know that isn’t necessarily the easiest thing in the world (See: Crawford, Carl). So losing Lester would be detrimental to the 2015 Red Sox and probably any future Sox team for the foreseeable future because finding that established ace is going to be as hard as finding a NFL game that doesn’t show a commercial with Peyton Manning singing about chicken parmesan.

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Not resigning Lester will also be detrimental to Ben Cherington’s resume when you think about it. The guy had all last year and the beginning of this year to sign Lester, and he probably would have cost way less then what he is going to get in the coming weeks. The fact that Ben couldn’t get him signed early on will cost him in the pockets if he decides to come back to Boston, but if he doesn’t he is going to take a big hit to his credibility as a general manager. This is Ben’s first real big test as GM of the Red Sox, we all know he really didn’t want to hire Bobby V in his first year, and yeah getting guys like John Farrell and Mike Napoli are substantial but signing Jon Lester is in a whole other category. Signing a guy like Lester will keep Ben in the good spirits of Red Sox Nation because it’ll show that he is willing to pay up for someone who we know will succeed in Boston. He is the sure thing, in a market of unknowns. Not resigning him will force Cherington to look elsewhere, at guys like Shields and Hamels who are either unproven in the postseason (Shields) or have looked like they are on the decline (Hamels).

Signing Lester has to be the number one priority if you are Ben Cherington, not signing Pablo Sandoval or anyone else for that matter. It starts and ends with Jon Lester. Not doing so will spell immediate doom for the 2015 Red Sox and Ben Cherington’s credibility as a top level GM. Listen winning a World Series in 2013 was great and it looks great on Cherington’s resume, but if we’re all being honest that was a miracle of epic proportions. Not to take away from anything that any of the players or front office people did that season, but winning the World Series in 2013 came as a shock to the majority of people if you asked them. So now Ben has the tall task of going back to that elite level, and the one guy that can take them there is Jonathan Tyler Lester. It’s Ben Cherington’s turn to make his first bold move as Red Sox GM, I’m hoping for the his sake (and the future of the Red Sox’s sake) he signs Lester for whatever amount he wants and for however long he wants.