Choosing the C over the B: A Red Sox fan on the Lester decision

By Alex Crowl

As the clock approaches 1 o’clock in the morning on Wednesday, Dec. 10, I am deeply saddened by the decision of the 2-time Boston Red Sox World Series champion Jon Lester to sign with the Chicago Cubs, on a 6-year 155 million dollar deal. This deal includes a 20 million dollar signing bonus making this contract worth around 100 million dollars more than what the Red Sox offered him this past season.

The Red Sox have made the decision to not sign players over 30 to large multi-year contracts and they disregarded that in pursuit of Lester. The disregard for their standards came up short. The glimmer of hope that remained for Lester returning to Boston finally ran its course. The entire free agent market on Lester was completely misread by the Red Sox organization, and they whiffed on one of the most successful players in Red Sox history.

The trend throughout Wednesday, and throughout the Major League Baseball Winter Meetings, leading into this decision by Lester was that he would not return to where his career began. He would not return to where he had been so prosperous as one of the premier left handed starters and aces in the game of baseball. I do understand the decision and would like to dissect it from an unbiased perspective no matter how difficult or possible that may be.

Jon Lester was low balled by the Boston Red Sox leading into the 2014 season with a 4-year 70 million dollar offer. Lester doubled that and more with the deal he has agreed upon with the club on the North side of Chicago. The Red Sox could have never seen the market for Lester increasing to the point it did with his prominent performance for the Red Sox and A’s in the 2014 season.

Certainly, the Red Sox may regret not offering him even 110 Million dollars initially prior to the season as Peter Gammons suggested. That could have potentially done away with this entire process. To reiterate, they could have never for sought Jon Lester would go at such an increased market value to so many different buyers, finally landing with the Cubs. Lester is going to end up making more than 100 million dollars more than he would have had he taken the offer of 4 years and 70 million dollars from the club that built him.

Jon Lester’s rationality on the process was simple. He went with the new challenge. Lester has already won two rings in Boston. What more did he have to prove to the loyal fan base? If Lester returns on 6-year 135 million dollar contract and doesn’t perform to finish out his prime, he could ruin his legacy in the entire New England sports kingdom.

In an organization that is looking forward to massive improvements in this next season making risky decisions signing above market value players like Pablo Sandoval and Hanley Ramirez, Lester could have simply been reading the writing on the wall. He may have felt he couldn’t live up to the expectations of Boston fans. He may not have had the motivation or the ability to end his career the way the Boston community expected of the legendary left-hander.

The idea of leading a new legacy for an up and coming organization with an incredible manager certainly is what was enticing for Lester. What does he have to lose on the North side of Chicago? He was offered more money and wasn’t treated poorly by a team now led by one of the best managers in baseball with the leading farm system in baseball. The difference between success in Boston and Chicago is so different that the decision leans towards the Cubbies.

The Cubs did not treat him poorly; the Cubs offered him more money. The Cubs have a better farm system, and the Cubs also have a lower expectation of what could be. If the Cubs are a .500 ball club next year are the fans going to be disappointed? Yeah, of course. Would they be as outraged as a Boston market, which has gotten used to a certain expectation of success in this millennium, absolutely not. Not to mention Lester has been an AL pitcher in a predominantly powerful hitting league dealing with the designated hitter his whole career. I’m sure mixing up the flow of batters he faced was a big plus for a pitcher entering his 30’s and potentially on the decline.

So many variables add up in this decision by the leading free agent in baseball, Jon Lester. This market led him to the decision of joining baseball’s infamously, unsuccessful organization. The memories I have of Jon Lester, being a die-hard Red Sox fan, will never leave my mind. I am saddened to the fullest extent at 1:14 in the morning on Wednesday, Dec. 10, as I was awaited this man’s decision. I fully understood where this decision was leading and I have the utmost confidence of Ben Cherington and the entire Boston Red Sox front office to make the right decisions to put a team on the field that the Boston and New England market can passionately respond to in the 2015 baseball season.

The introduction provided as a forecast for this free agency was that starting pitching, and pitching in general, would be heavily available, and that the top bats would be few and far between. The Red Sox not only signed the top bat, but they reeled in the top two bats, and for that I am thankful.

I would like to thank Jon Lester with all that I am for the joy that he has provided me and would like to wish him the best of luck. I have been a big advocate of the moves made on the north side of Chicago, and truly believe they are and will be a great competitor moving forward.  The proceedings that have occurred thus far in San Diego, Calif. during the Winter Meetings have built up an incredible following for the 2015 season, and I cannot wait to see what all of these teams provide for personnel come that glorious day in April where baseball is king.

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