Why We Should Be Disappointed in Ben Cherington

Ben Cherington has had an up and down ride during his tenure as Red Sox general manager, his first official move wasn’t even his idea. Remember Bobby Valentine? Yikes what a mistake that was, but when it came out that hiring Valentine was more of a owners decision than it was Cherington’s we gave him a pass for that.

Then came the deal that saved the Red Sox from potential years of misery, in a late August blockbuster the Red Sox managed to trade away Adrian Gonzalez, Carl Crawford, and Josh Beckett (along with Nick Punto) to the Dodgers and had to pay a fraction of their salaries in the future. That can be seen as Cherington’s best hour because in doing that trade the Red Sox freed up more than $250 million dollars through the end of this decade.

And then came the 2012 offseason when he signed a bunch of misfits like Shane Victorino, Jonny Gomes, and Koji Uehara, all in all there were relatively low expectations for the 2013 Red Sox. However thanks to phenomenal play by all 25 men they were able to shock the baseball world by capturing the 2013 World Series by defeating the St. Louis Cardinals.

During that offseason the Red Sox lost Jacoby Ellsbury who many agreed wasn’t worth the money that the Yankees paid him, alongside the fact that it was apparent Ellsbury did not want to be in Boston after his contract was up. So coming into 2014 the Red Sox didn’t add any superstar names, instead settling on low key signings hoping that they could strike lightning in a bottle for the second time in two seasons.

Well that didn’t turn out so well thanks to lackluster play through the first 2 months of the season, which lead many Red Sox fans wondering if they would be sellers come the trade deadline. There were rumors swirling that Jon Lester would end up being traded in hopes of getting a ‘kings ransom’ in return. Lester who’s contract expired after the 2014 season, had not reached an extension with Cherington and the Sox during the early part of the season (Keep that in mind for later).

So when the July 31st deadline came the Red Sox struck a deal with the Oakland Athletics that saw Jon Lester and Jonny Gomes be sent to Oakland in return for Yoenis Cespedes. The trade was met with mild reaction, some Red Sox fans were hoping for younger prospects that could develop and be a pivotal factor down the road, while others were excited the Red Sox were able to land a big bat for the middle of their lineup. 2014 proved to be a bust for the Red Sox, going 71-91 and finishing last in the AL East.

Up until last night many had wondered whether Jon Lester would return to the Red Sox, initially it appeared that the two sides were to far apart in terms of dollars and length of a contract. However as the days past the Red Sox appeared to be more and more involved in the negotiations with the southpaw, and were even seen as favorites among beat reporters. Ultimately Lester decided to take his talents to the Chicago Cubs, signing a 6 year/$155 million dollar deal, leaving the Red Sox without their homegrown pitcher and now on the look for a new number 1 starter.

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What frustrates me and probably a good chunk of Red Sox fans is the fact that the Red Sox could have prevented all this from happening if they had just offered Lester a respectable offer back in Spring Training. The Red Sox reported offer was somewhere around 6 years/$135 million dollars, which in all likelihood would have been enough for Lester to sign this time last year. Coming off a fresh World Series win, Cherington had to of thought that signing Lester right after he pitched his butt off in the World Series would have been buying him at his absolute highest, which is why I believe they presented that supposed 4 year/$70 million dollar offer last year.

What is puzzling to me is what was Ben Cherington thinking by not buying Jon Lester last year, even if his value was at his absolute highest? Lester has made it very apparent that he would have stayed, even take a hometown discount because he loves this Boston and can’t envision leaving the clubhouse that he grew up in. So even if Lester would have exceeded $100 million dollars, in the long run he would have been worth it because he has proven over the years that he can be that ace that this rotation needs.

Lester had been an excellent anchor to this rotation since coming in late 2007, he had the ability to provide quality starts every fifth day and he was even better once October came. I mean for goodness sakes Cherington do you remember how good he was last postseason for you guys? He was one of the main reasons we took home the World Series trophy, his ability to step up when the lights were brightest proved that he was a big game pitcher. What else did you need to see before you could offer up a $100+ million dollar offer?

So now instead of having your number 1 pitcher locked up for most likely the remainder of his career and having him sign in all likelihood a deal similar to what they just offered to him, the Red Sox are now on the hunt for a ‘new’ Jon Lester. I wrote when the Red Sox signed Pablo Sandoval and Hanley Ramirez that it wasn’t the best move at the time, and that they should focus all of their attention on Jon Lester. I posed the question that the signings could be a sign of Cherington’s incompetence as a general manager? I believe after letting Jon Lester get away, Cherington is an incompetent general manager.

Tell me how or who you can bring in that would be a upgrade over Jon Lester, or even who would be comparable to Jon Lester. The answer is nobody can replace Jon Lester, his dominance in Boston is something Red Sox fans haven’t seen since Pedro Martinez left the Red Sox in 2004 (that’s called irony right?). In all likelihood the Red Sox are now going to have to shop around and likely strike a trade just to get someone who is a slight notch below Lester, whether that may be Cole Hamels or James Shields but one thing is for certain this is not the smartest way to conduct business if you are the general manager of the Boston Red Sox.

Red Sox fans, I am cautioning you now that Ben Cherington has a very inconsistent track record so far as general manager of your Boston Red Sox. If it wasn’t for Magic Johnson and the L.A Dodgers bailing them out in 2012, god only knows how much trouble they would be in today. Letting Jon Lester go means only one thing: Ben Cherington is incompetent as general manager of the Red Sox, and should be let go sooner rather than later. Who do you replace him with? I don’t know and frankly I don’t care, all I know is this man let one of the best pitchers in baseball get away because he would not show him the respect that he so rightfully deserves.

For all Lester has done and accomplished in his career, I can not blame him one bit for leaving Boston. He deserved more respect than Ben Cherington and the Boston Red Sox owners gave him (or did not give him). For that I say, Jon Lester good luck in Chicago. I hope you lead the Cubs to their first World Series and then tell Ben Cherington and Larry Luchhino to shove it.

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