Jon Lester had barely thrown a pitch for the Red Sox when his cancer was announced. For this reason, it's nearly impossible to separate Jon Lester, Red Sox pitcher, from Jon Lester, cancer survivor and two-time World Series champion. If Boston fans feel some claim of ownership of Lester that goes beyond the standard he's-our-type-of-guy schtick, this is probably why we do.
It does not take an advanced degree to understand why Lester chose the Cubs over the Sox. Firstly, there was $20 million more to their deal, akin to a whole year's worth of work. Lester said that he wouldn't take the richest deal out there just for the sake of doing it, but $20 million between attractive offers isn't pocket change.
Lester obviously has a relationship with the Cubs front office as well, given that it's basically the same front office that nurtured him with the Sox. When I imagine Theo Epstein selling Lester on the Cubs, I imagine him saying nearly the same things he said to Curt Schilling on Thanksgiving Day, 2003 with respect to becoming sports-immortal, and I imagine Lester taking to those thoughts. Why wouldn't he? It's a real enough chance to win a title with the Cubs. That's big, and it was a subject of his introductory press conference for a reason.
I don't put much stock I put in the "Lester felt disrespected by the Red Sox's offer from the previous summer, so he went elsewhere" narrative that is making the rounds, and not for the first time. Deadspin's Barry Petchesky (who is OBVIOUSLY BIAS11!1!) says the Sox lost the chance at signing Lester because of their 4-year, $70 million offer in the 2013 offseason, and while there's a whiff of truth to it, it's equally possible that the Sox might have felt they didn't need Lester at the price he ultimately commanded.
None of this is to say that the Sox didn't flub the "negotiations," such as they were, before 2014. It seems like quite the leap of logic to consider this the substance of the argument, instead of a relatively minor detail. It's not like Lester spurned a $135 million offer from the Sox to play for the Cubs for $70 million: he took a better deal.
In fact, what he took isn't really a "deal" at all -- it's a sticker-price payment on a luxury car. New Cubs manager Joe Maddon said landing Lester was like "winning the lottery," which begs the question of what lottery costs north of $150 million to win. I know, I know: it's not his money, and there's no real chance of it running out. The Cubs are rich and stocked with cheap young talent. They could afford Lester without a real problem.
If the Sox won't pay Lester, will they pay anyone?
The Red Sox' search for an ace probably isn't as simple as throwing the unused Lester money at someone, either now or a year from now.
The Sox are in a different position. They didn't need Lester, but they needed to attend to his dog-and-pony show, if only to show they weren't heartless dolts. I'm not claiming omniscience on Ben Cherington's part, but some part of me thinks he didn't really want Lester back at full price, and not for any personal reason. The Sox just have too many rotation holes to fill at this point to get emotional about it. They just had to appear emotional about it so we wouldn't lose our marbles.
All of which leads to a final, obvious point regarding Lester: he wasn't ours to lose. We sent any real claim of him to Oakland for Yoenis Cespedes, a trade both teams would do over in a heartbeat. He was no longer a Red Sox star for life. You can't play the Cal Ripken card when you've traded it to Billy Beane.
All of this is a way of saying the Sox would have been good with Lester, and they might be better off without him. He was the biggest name at the Winter Meetings, but he was still only the first name on the market. The Cubs overreacted because they've been waiting for this moment for years. We've merely been preparing for it, and we still weren't ready.
Maybe that's the point. Maybe Lester was gone the second he shipped off to Oakland, and we've been chasing the wrong dream. Maybe the chase was Cherington's (and John Henry's) way of showing they get it. They get what we're about and why we wanted Lester back. They didn't ensure they got him because they ultimately know us better than we know ourselves. As much as we loved Lester, we love the Red Sox more. It's never about our last great pitcher. It's always about the man almost certain to be our Opening Day starter: the next one.