The Chicago Cubs are building to win now, regardless of the talk

Don’t let me mislead you, the Chicago Cubs are assembling a fantastic farm system with depth all around, and if things continue as they are, they will remain competitive for many years to come. But if you look to the Jon Lester signing, the Cubs are looking to win now no matter what they may say publicly.

When the Cubs signed Alfonso Soriano following a last-place finish in 2006 to a $136 million contract, that wasn’t for the future, it was a “now” deal. And to an extent, it worked out that way. The team won back-to-back division titles in 2007 and 2008, but because the farm system wasn’t built for the long haul, the door slammed quickly on the Cubs.

Before Soriano finally approved a trade to the New York Yankees in 2013, his contract earned him more than his share of boos. For that kind of money over that duration, you don’t get to become the face of the organization, you’re immediately it because you’re paid to be. It becomes less about your numbers on the field and more about the ones on your paycheck.

Enter Jon Lester.

Lester said in his introductory press conference that he understands what’s at stake for the franchise, and what the fans feel for this Cubs team. I’ve never been to Boston, and I know they waited a long time too. But Lester may still be surprised by what’s expected of him.

The Cubs will pay him near $175 million, with bonuses included. Lester has averaged 16 wins a season. That immediately brings the ace label to him, even with the emergence of Jake Arrieta. Do the Cubs expect those 16 wins to bring an NL Central title home? Well, yes and no.

Theo Epstein and Jed Hoyer have been methodical in their development of “the plan”. Build depth in the farm system, release unwanted payroll and then sign key free agents with that freed up money. Check, check and check. Key prospects have made their way to Wrigley, but there are more in the pipeline just in case. And the two best in the organization, Addison Russell and Kris Bryant are yet to come.

To get Lester, it was going to take a mega deal. The Cubs also knew the risk of signing a pitcher to a long-term deal at 31-years-old (He turns 31 on Jan. 7). Before this deal is done, Cubs fans may be booing Lester because he isn’t winning 16 games anymore at 35-years-old. The difference is the Cubs have built a long-term plan, woven in with the win now mentality.

So even if Lester starts to decline, the Cubs aren’t simply relying on him over the next six-years to do this alone, but heavily in the next two to three years to help win now. The Cubs are relying on the home-grown players to succeed, but they’ve built safety in numbers just in case.

I don’t always agree with the terms, “built for the long run”, or “built to win now”. Each can give the wrong idea. While many aren’t sold the Cubs are ready to win this year, they’re trying to. Joe Maddon and Lester weren’t “in a few years” type of signings. With these guys, it is to win now. With Bryant, Russell and the plethora of prospects in the system, that’s for a bit of later.

But the Cubs have put themselves in the best of both worlds, regardless of which they say they’re in.

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