Chicago Cubs Will Be Major Players If Jon Lester Reaches Free Agency

By Daniel Schmelzer
Jon Lester Boston Red Sox Rumors
Bob DeChiara-USA TODAY Sports

According to Ken Rosenthal of, the Boston Red Sox recently offered their ace left-handed pitcher Jon Lester a four-year extension worth somewhere between $70 and $80 million. While that is obviously a lot of money, the offer is far under market value, as Lester would receive much more as a free agent. Rosenthal reported that Lester not only turned down the Red Sox’ offer, he does not want to resume negotiations until after the season.

It appears that Boston’s low-ball offer could make them lose their ace, as he is set to become a free agent this offseason. While countless teams will obviously be interested in Lester if he hits the open market, I think the Chicago Cubs would be near the top of that list.

The Cubs have one of the top minor league systems in all of baseball. Offensive prospects like Javier Baez, Kris Bryant and Arismendy Alcantara should reach the big leagues soon. Add them to the core of current Cubs Starlin Castro, Anthony Rizzo, Mike Olt and Welington Castillo, and the offense has a ton of potential. Unfortunately, the Cubs’ pitching appears to lag far behind their bats. Sure they have some interesting arms, but it is obvious that they will need to add starting pitching through free agency if they are going to be competitive in the near future.

With Lester, Max Scherzer and Justin Masterson all seeming to be possible (probable?) free agents next offseason, the Cubs could be in a great position to address their need. It is always hard to guess what each team has to spend, but with a bottom-ten payroll in a big market, I have to imagine the Cubs will have enough money to sign at least one of these guys.

There will be plenty of pitchers who would make sense for the Cubs, but I think Lester could be the best fit, and maybe the most realistic. The 31-year-old lefty has a long track record of consistent success and would be a perfect addition to place at the top of the Cubs’ rotation.

While money is usually the most important factor in free agency, the Cubs may have an advantage on their opponents when it comes to Lester. Cubs President Theo Epstein, GM Jed Hoyer and others in the front office were key members of the Red Sox during Lester’s development through the minor leagues and his success in the big leagues. Epstein was the one who signed Lester to a long-term deal with Boston back in 2009.

Whether his connection to the front office matters or not remains to be seen. That said, I cannot imagine it will hurt and could be a tiebreaker if the Cubs are willing to spend what it takes to land Lester. The need for a front line starting pitcher is there, and the front office is obviously a fan of the player. I think the Cubs will definitely be major players if Lester hits the open market.

Daniel is a Chicago Cubs writer for Rant Sports. Follow him on Twitter @D_Schmelzer, “Like” his Page on Facebook and add him to your network on Google.

You May Also Like