Chicago Cubs in Great Position to Land Lester, Here’s Why

Jon Lester, Chicago Cubs

When Jon Lester was dealt to the Oakland A’s at deadline, many were worried about what this could do to Lester’s free agency intentions. Before the trade, many thought Lester would simply re-sign with the Red Sox; however, all of that may have changed when he was traded. Now that Lester was traded, the Red Sox can no longer offer a qualifying offer with the draft pick attached.

Out of all the possible suitors, the Cubs seem to be in the best position to challenge Boston for the ace’s services. Lester still has connections with the Cubs front office, primarily with Theo Epstein, who was general manager when Lester won his first World Series in 2007.

Ever since the Theo/Jed braintrust has been in charge of the Cubs, they have preached cutting payroll and smart spending, well they have gone from the sixth highest payroll in 2011 (last year of the Jim Hendry era), to 23rd at opening day, 2014. The Cubs were heavily linked to Masahiro Tanaka; however, they were ultimately outbid by the New York Yankees. What this showed, other than the Yankees still have too much for their own good, was that, for the first time the Cubs were in position to spend.

In past years, the Cubs have been on something of a spending freeze, waiting for the last of Jim Hendry’s contracts to expire, before making serious “splashes” in free agency. Perhaps the biggest contract, the now-infamous Alfonso Soriano deal finally comes off the books this winter, possibly freeing up enough cash to make a push at Lester. According to some teammates , Lester is reportedly looking into signing with the Cubs, to be reunited with Epstein and Jed Hoyer. 

Lester, who will be 31 by next opening day, announced that he would be open to re-signing with Boston, even if he were to be traded. However, those instances don’t happen particularly often, and Theo Epstein has been known to be able to attract free agents with skill. It’s still premature to say which way it’ll go, but don’t be surprised to see the Chicago Cubs’ name attached to Lester. James Shields and Max Scherzer are also on the market this offseason, and could garner interest from 1060 W. Addison.

The Cubs, who are starting to see the “future” of the organization come together with Javier Baez, Arismendy Alcantara, Kyle Hendricks, and possibly Jorge Soler all making major league debuts this year. The Cubs could use this as a primary sales pitch for Lester, who is rumored to be looking for a ready-to-compete team.