Where Will Jon Lester Cash In?

Posted on December 15th, 2014 by Matt

Until a few months ago, Jon Lester’s entire career has been played in a Boston Red Sox uniform. Lester has had considerable success with the Red Sox, and the team has had great success as well. For those reasons, most people assumed that Lester would be a lifelong Red Sox member despite his impending free agency. It seemed like only a matter of time until the two sides would agree on a contract extension that would keep Lester in place throughout his prime.

Maybe not so fast. Prior to the trade deadline this past season, Lester was traded to Oakland for Yoenis Cespedes. Of course, at the time, the Red Sox were out of the race and didn’t want to risk losing Lester for nothing at season’s end, so they made the move to add the Cuban slugger. Even still, many people expected that once the season ended, Lester would sign back with Boston. However, as the offseason has moved along, it has become clear that the Red Sox aren’t the only team with designs on signing the powerful lefty.

The Windy City Comes Calling

While the Red Sox are still very much in the mix for the services of Lester, the lesterChicago Cubs are another strong contender who appears will to spend big (among others, such as the Giants and Cardinals). The Cubs are in a great position to bring in a high priced free agent because much of their roster is made up of young, talented, and affordable players. If they can combine and experienced veteran with the ability of a Jon Lester with their young core of talent, the fortunes of the Cubs could finally be turning around. In the end, the team that is able to offer an extra year on the contract will likely be the one to win the bidding.

Which City Offers More Potential?

While the past decade would indicate that Lester would be better off returning to Boston if he wants to win, the future might look different than the past. The Cubs are a young and talented team, and the Red Sox are signing older free agents in an effort to recover from a disappointing season. Only a year removed from a World Series title, the Red Sox seem to be farther away than they have in recent years. Of course, the addition to Jon Lester would go a long way toward putting Boston back near the top of the A.L. East.

The money that is offered to Jon Lester is likely to be pretty similar between Chicago and Boston, so it will likely come down to where he prefers to pitch. Does he go back to the familiarity of Fenway Park, or accept a new challenge with a young Cubs team? It will be interesting to see how this decision is settled.



2020 TOPPS CHROME SAPPHIRE EDITION JON LESTER #306 CUBS picture
2020 TOPPS CHROME SAPPHIRE EDITION JON LESTER #306 CUBS
$1.99


2014 Topps Heritage Chrome Purple Refractors Baseball Card #431 Jon Lester picture
2014 Topps Heritage Chrome Purple Refractors Baseball Card #431 Jon Lester
$0.25


Topps Fire Jon Lester #109 picture
Topps Fire Jon Lester #109
$1.1


Chicago Cubs Coolbase Authentic - Jon Lester #34 Size 48 Rare Gray Alternate picture
Chicago Cubs Coolbase Authentic - Jon Lester #34 Size 48 Rare Gray Alternate
$200.0


Jon Lester, 2019 Topps Heritage (#405), photo variant SP, Chicago Cubs picture
Jon Lester, 2019 Topps Heritage (#405), photo variant SP, Chicago Cubs
$3.0


2018 TOPPS GOLD JON LESTER & 2019 ALLEN & GINTER CARDS CUBS picture
2018 TOPPS GOLD JON LESTER & 2019 ALLEN & GINTER CARDS CUBS
$0.99


Jon Lester 2010 Bowman Platinum #95 Lot Of 3 Red Sox Cubs picture
Jon Lester 2010 Bowman Platinum #95 Lot Of 3 Red Sox Cubs
$0.99


Jon Lester 2015 Topps Triple Threads Autograph Memorabilia 03/18 picture
Jon Lester 2015 Topps Triple Threads Autograph Memorabilia 03/18
$15.99


Jon Lester 2007 Topps RC #383 picture
Jon Lester 2007 Topps RC #383
$1.1


Jon Lester 2016 Topps Series 1 #151 Chicago Cubs Pitcher - Like New picture
Jon Lester 2016 Topps Series 1 #151 Chicago Cubs Pitcher - Like New
$0.76


2018 Topps Chrome Jon Lester Chicago Cubs #191 picture
2018 Topps Chrome Jon Lester Chicago Cubs #191
$0.99


2011 Topps Topps 60 Jon Lester T60-95 picture
2011 Topps Topps 60 Jon Lester T60-95
$1.27


    Next Page >>