Jon Lester: What If?


Sep 24, 2014; Oakland, CA, USA; Oakland Athletics starting pitcher

Jon Lester

(31) pitches the ball against the Los Angeles Angels during the first inning at Coliseum. Mandatory Credit: Kelley L Cox-USA TODAY Sports

Jon Lester was added to the 2014 Oakland Athletics for one reason: to win a big game. Even with Lester, the A’s failed to achieve that feat. I know that the idea is farfetched, but what if Lester enjoyed the group of guys the A’s have in the locker room, and feels he let them down? The southpaw is due for a big payday this offseason, but would he settle for a decent payday, and return to Oakland, if he feels this team can contend?

As the Daily News wrote late on Monday night, the Yankees have removed their name from contention for Jon Lester. The Daily News also says that the Yankees are more concerned with re-signing former Athletic, Brandon McCarthy than going after big-time free agents.

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A typical landing spot for hot free agents is Boston, but at the end of September, Jon Lester put his home in Boston on the market. While this doesn’t necessarily exclude the Red Sox from the running, it could signal that there are other spots he’d like to go.

The Chicago Cubs are another rumored team in contention for the lefty, with a wealth of prospects due to come up, and a new, eager manager in Joe Maddon. A lot is expected of the Cubs, and one area they could use some help in would be their starting rotation.

A lot could depend on where Max Scherzer and James Shields end up. The Tigers could become players in the market as well, if they lose out on Scherzer.

There isn’t a surefire answer to the question: “Who is the frontrunner for Jon Lester?” Lester has played with Oakland for a brief stint of time. If he feels like they can contend, and win a Championship, that may be enough for him to sign on the dotted line. Of course, the A’s will have to pony up, but Lester has made $43.5M over the course of his career. He strikes me as a person that doesn’t necessarily just go with the flow. Would he like the extra money? Of course. Does he need it? Probably not.

Of course, this is all speculation. Will it happen? Probably not. Yet, the A’s have already landed him once, out of nowhere. Why can’t they do it again?