No. 31 is, of course, retired by the Cubs for two Hall of Famers, Fergie Jenkins and Greg Maddux, so Lester couldn't wear it in Chicago. He chose jersey No. 34, last worn by Kerry Wood.
Wood can be a polarizing figure around here so let me state that despite his popularity, his number should never be retired. He just wasn't that good, unfortunately, due to injuries. I like the idea of Lester wearing it. The number was popularized by another Hall of Famer, Nolan Ryan, who wore it in 1966 with the Mets and then from 1980 through 1993 with the Astros and Rangers. The fact that Ryan wore it during Kerry Wood's teenage years is quite possibly the reason Wood wore it in the first place, as Wood grew up in suburban Dallas while Ryan was playing for the Rangers.
We all know what Jon Lester has done in his career; that's the reason Theo & Co. were willing to give him the largest free-agent contract in Cubs history. Here's what Theo said about signing free agents just a few days before he landed Lester:
"You have to be aggressive if you hope to get something done," he said. "In this current landscape, a lot of teams have money, and good players are at a premium. There's more demand than there is supply for elite players, there's no doubt about that. "But you also have to maintain some sense of discipline and limits and long-term perspective. If you go into free agency thinking you're one player away and you need any one player at all costs, you're probably going to end up getting burned. You're probably going to end up with an organization not as healthy as it can be years down the line. "That said, there are players who are important and there's a time to be very aggressive and a time to know what you want and do everything in reason to get it. You have to balance those interests. I think I said free agency is not for the faint of heart, and it's not -- both ways." There are few short answers with Epstein, so he elaborated further on this. "You have to be prepared to be ultra-aggressive if you want to come way with what you're looking for, and you also have to be prepared to fail," he explained. "You have to be able to accept not landing the player because there are always other alternatives, and you can't go in to any pursuit at all costs, throwing reason to the wind. "You also have to be prepared to fail when you do land the player; contracts don't always work out. So the key in that respect is to build the organization up to a point where you can recover from any one player not performing and you have young players ready to step in."
I believe this is exactly correct. Theo got the player he wanted, and I'm certain he understands the risks in giving out a contract as long and as for many dollars as he gave Lester.
Here's hoping for big years from Jon Lester, particularly in the early years of the deal. If he can do that, the Cubs will be a big step closer to a World Series title.