Sports Fan Vs. Red Sox Fan: Do I Root for Jon Lester Tonight?

I’ve been debating this one since July 31st. I don’t know whether or not to root for Jon Lester this October.

Your initial response is probably “What the hell??!! How would you not root for Jon Lester?” And that’s fair, because that’s how I’m thinking. Of course, it’d be awesome to seen Lester destroy 3 American league teams (including the wild card game tonight) and then shut down some lowly National League peasants like the 2007 Rockies and 2013 Cardinals. Then he could come back to Boston this winter with yet another dominating postseason on his resume.

But that’s the thing: The Red Sox have to resign him, and the market for Lester is going to be insane. Max Scherzer turned down 6 years and $144 million before the season, and Lester will probably get more than that, pending the next few weeks. Scherzer is a grand total of 6 months younger than Lester, and Lester has the kind of postseason pedigree that will make big market, hungry-for-a-championship general managers get a little bit of a pants tent. To be fair, Scherzer’s postseason past isn’t too shabby, as you may remember from Games 2 and 6 of the ALCS last year, but Lester should get more than Scherzer.

All this is to say that Jon Lester will command a lot of money this winter, and anything he does positively this postseason could add to that total more than we realize. And this is where the baseball fan in me clashes head on with the Boston Red Sox fan in me. Do I root for the awesome baseball story with the connection to the Red Sox, which is watching a guy that we love dominate October again, or do I ruthlessly abandon anything that involves entertainment and only root for what helps the Red Sox, which would be watching Lester uncharacteristically fail and drive down his free agency price tag.

Simply put, do I root with my heart or my head?

Simply put, I have no idea.

It’s not often when being a diehard fan of a sports team gets in the way of being a diehard sports fan. The other example that comes to mind easily is my reluctance to watch regular season NBA games that don’t involve the Celtics, but I think part of that is due to the fact that NBA regular season games are often truly boring. It’s far more rare for something like this to happen: a situation in which me as a sports fan and me as a Red Sox fan are going full throttle with no other impediments (like regular season NBA games often being boring), and the two clash head on.

It’s kind of depressing, honestly.

Loving sports paved the way for me to become a diehard Boston sports fan, which of course paved the way for this website. But now, rooting for the Big Four teams of the area is such a drug that, which is why I’ll always feel a little bit cheated if Brady and Belichick don’t win another Super Bowl and if this Bruins core doesn’t win another cup. Especially when you’ve tasted your team’s success, you want more of it, just like a drug. But more importantly, the act of rooting for a team, winning or losing, is the drug.

As for tonight, I’m gonna wait until the game starts and then see who I’m rooting for. This will be a great experience for me, actually. Am I watching sports nowadays primarily with my head or my heart? I don’t know, but I’ll find out tonight and maybe throughout the 2014 MLB postseason. Being a sports fan is the type of mindset where people almost always feel VERY strongly about where their interests lie. But the fact that I don’t know who I’m rooting for tonight is a sign that, like so many other parts of life, being a sports fan occasionally becomes a personal tug of war.

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