Why Jon Lester Needs To Sign With The Chicago Cubs

By Evan Massey | Dec 8, 2014

Aug 7, 2014; Oakland, CA, USA; Oakland Athletics starting pitcher Jon Lester (31) throws to the Minnesota Twins in the first inning of their MLB baseball game at O.co Coliseum. Mandatory Credit: Lance Iversen-USA TODAY Sports /

Jon Lester will choose between the Chicago Cubs and San Francisco Giants in MLB free agency.

There has been quite a bit of drama surrounding the free agency chase for ace starting pitcher Jon Lester so far this offseason, but it is nearing an end as Lester has narrowed down his options to just two teams. According to a report from Ken Rosenthal, the Chicago Cubs and San Francisco Giants are the two teams that Lester will choose between in the very near future.

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Both teams would be good landing spots for Lester, but the Cubs might give him the best place and more enjoyable situation. He has a very close relationship with Theo Epstein, and would be pitching in one of the most historic baseball cities for one of the most historic teams. San Francisco is built to win now, while the Cubs are built to win in the next couple of seasons with an incredibly talented farm system on the way up.

Sources: Barring late change, Lester choosing between #Cubs, #SFGiants.
— Ken Rosenthal (@Ken_Rosenthal) December 8, 2014

So who should Lester end up choosing to play with in what could very well be his last big contract?

Quite simply, the Cubs would be the best lock for him to continue his legacy and would be more what he is looking for at this point in his career. He would be overshadowed by Madison Bumgarner out in San Francisco, and in Chicago he would be viewed as one of the savior’s of the franchise. If he was able to lead the Cubs back to postseason contention his legacy would immediately take a jump.

San Francisco likely would offer him a chance to win a World Series over the next year or two, but he would no longer be the number one guy in the rotation. It all comes down to what Lester is looking for, and whether he wants to play a larger role and help break another curse and become a hero, or play a second fiddle type of role and have a better chance to win now.

Chicago has built their franchise to the point where they are considered to be long-term contenders when their young talent develops. They saw both Javier Baez and Jorge Soler take the jump to the majors last season, and Soler especially showed future star potential. The only issue that the Cubs had last season was pitching, and Lester could be a huge quick fix for that.

Not only do the Cubs want to sign Lester to take over as their ace, they also agreed to a two-year contract with Jason Hammel. He will help shore up the middle of the Cubs’ rotation, and is the second starting pitcher that Epstein wanted to sign.

Offensively, the Cubs aren’t expected to have many issues during the upcoming season. Their young talent is going to be even better, and they saw both Anthony Rizzo and Starlin Castro play major roles last season. Chicago would like to sign a catcher, and Miguel Montero is a name that continues to be brought up in rumors.

While the Cubs look very good in the future and likely would be a better long-term fit for Lester, the Giants can offer the winning immediately card. It’s always hard for a star player to turn down the chance to compete for a championship immediately, and that is one of the main draws to San Francisco.

When everything is said and done, it all comes down to whether or not Lester wants to build on his legacy with a good chance at championship contention in the future or whether he wants to chase a ring as a second best pitcher. Both teams are going to offer him lucrative contracts, but the Cubs are simply the better fit for him at this point in his career.

It will be very intriguing to see who Lester ends up picking over the next few days, but the Cubs seem to be his best option. San Francisco is still making a heavy run coming off of a World Series win, but Lester’s friendships with Epstein and Ryan Dempster might be just enough for Chicago to come out on top. All of this speculation is fun, but we won’t know anything until Lester makes up his own mind.

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