Jon Lester is my New Man Crush

He hasn’t even been officially added to the 40-man roster, but Jon Lester is fast becoming my favorite Cubs player. Sure, it’ll take a lot to surpass Anthony Rizzo and Starlin Castro (yes, I’m one of those starry-eyed apologists), but Lester is sure doing everything he can to entice me to buy a new shirsey.

With almost four months between now and his first meaningful pitch for the Cubs, Lester can’t make an impact with his performance on the field. Off it, however, he’s already coming up aces. First, Jon Heyman reported that Lester contacted the San Francisco Giants personally to let them know of his decision not to play for them.

That may seem like a basic courtesy, something every team should be afforded, but I’d be willing to bet that agents are the ones handle almost all of this communication in other cases. Heck, it might not even be the agent, but an assistant of some sort. Lester didn’t owe the Giants anything, but he made that effort anyway.

Then came the news that the newly-minted second-highest-paid pitcher in baseball took to Twitter to address well-wishers and detractors alike, according to CSN Chicago’s Tony Andracki. I find it pretty amazing that Lester would send out personal responses at all, let alone to those who were disparaging him.

I can say from personal experience that this isn’t a very thing to do. Perhaps it’s easier to take the high road when you’ve just been given $155 million, but I applaud Lester’s gestures. I only have around 1,600 followers and I sometimes find it difficult to respond to every mention I get.

That was certainly the case the other day, when my article about Lester signing with the Cubs was shared by ESPN college basketball analyst Dan Dakich. Dan’s got around 80,000 followers, some of whom were none too pleased with my work and weren’t shy about letting me know how they felt.

I allowed the false bravado of a couple people hiding behind the anonymity of Twitter handles to get under my skin and I engaged with them, knowing full well that it was a futile effort. If I’m being honest, it’s still sticking in my craw as I type this. But Lester’s approach is something I can learn from as I move forward and perhaps reach a wider audience.

And just this morning I read an article by Yahoo’s Jeff Passan claiming that it was a couple simple items of camouflage Cubs gear that helped tip the scales in Lester’s decision. Okay, it was a bit more involved than that and I’m sure the payday didn’t hurt. But the kitschy apparel is indicative of both Lester’s mindset and the Cubs’ approach in wooing him.

In Lester, the Cubs have a guy who is interested in building something, in standing at the forefront of a youth movement that has been gaining steam ever since Theo Epstein came to town. In the Cubs, Lester sees an organization not unlike the one he played for in Boston. That 2003-04 Red Sox team saw its hallowed ballfield brought into modernity with the additions of video boards and myriad signage.

Eleven years, two World Series titles, and one victory over cancer later, Lester is older and wiser but is excited for the opportunity to help history repeat itself. He knows what it’s like to bring a title to city and an organization starved for one and that’s an experience he’d love to go through again.

Can you imagine what it would be like to be a part of championships with both the Red Sox and the Cubs? That’s what brought Theo Epstein and Jed Hoyer to Chicago and they were able to express that desire to Jon Lester in a manner that convinced him to eschew his career history, his home, and more guaranteed money.

You’d like to think that every professional athlete had the drive to want to make history or to be a leader of men, but I think we all know that’s not always the case. And I can’t blame any of the guys who want to be just another really good player on a title-ready team. Jon Lester, however, doesn’t appear to be one of them.

In choosing the Cubs, Lester is taking on the mantle that comes with being “the man.” He has assumed the seat at the head of the table with a team that may end up being known as the Jons of Anarchy. They’re shaking loose the unwritten rules that say the Cubs can’t win, that they’re the lovable losers of baseball.

Lester’s legacy in Chicago will be written in wins and losses, not just for him, but for the team as a whole. But with his recent actions, he’s already penned himself a striking foreword. I can’t wait to see what the ensuing chapters hold.