With Jon Lester, Cubs Officially Force Window Open

We all knew that the time was coming. The Cubs themselves talked rather openly about it. Blessed with the best system in baseball, the Cubs were coming up on a period of hopeful contention. The soft target, for many, was 2016. By that point, enough prospects might’ve established themselves, and the Cubs would be able to gun for the playoffs. But it was always reasonable to think the Cubs might try to accelerate things. That they might hit that transition between stockpiling and spending, and spend big to hurry things up. There was a way for the Cubs to become a potential playoff team next season. Whether you think they’re there yet, the Cubs have now checked off a lot of boxes.

In Jason Hammel, the Cubs just locked up a pretty talented starter for the back of the rotation. In Miguel Montero, the Cubs upgraded behind the plate, getting kind of a poor man’s Russell Martin equivalent. And now the Cubs have their big fish, agreeing with Jon Lester for six years and $155 million. For Lester, the Cubs were long considered a favorite, but there’s a difference between something being possible and something getting done. We can now, officially, say this: the Cubs are ready to try to go to the playoffs. There’s no mistaking their intentions, and Lester’s a giant upgrade.

In a sense, this is when it’s most anticlimactic. We’ve already written and read about how Lester has changed, and which teams could end up with him. You’ve already thought about the Cubs adding Lester before, so now they’ve simply gotten that done, and you can think thoughts you’ve already thought. But it’s still worth a rundown now that we have an official decision and official terms. What do we make of the Lester domino falling? We’ll proceed in three sections.

Do the terms make sense, overall?

The Cubs inked Lester for $155 million. According to reports, the Red Sox offered the same number of years, but $20 million less. What that makes it sound like is a desperate overpay. In reality, the numbers don’t make it look godawful. Depending on what you do with them, this might even look totally normal.

For example, consider what ZiPS has to say about Lester’s next six years:

In a neutral park, ZiPS projects 6/151 for Lester. That’s why you’re hearing talk of 150-160 and it’s not completely crazy.

— Dan Szymborski (@DSzymborski) December 10, 2014

This is where we get into the art of things. The last three years, Lester has averaged about 4.5 WAR. On one hand, you’d want to project a decline, but on the other hand, Lester is also coming off by far his best season of the three, with some demonstrable changes to his approach. It wouldn’t be unreasonable to figure Lester might be a 4.5-win pitcher next season. What if you set the cost of a win at $7 million, and then inflated by the customary 5%? Then given the standard half-win per-season decline, Lester would be worth about $151 million.

And what if you set the cost of a win at $7.5 million? The market’s been pretty crazy so far. Then you get Lester being worth about $162 million. Alternatively, what if Lester is a 4-win pitcher? Then you’re more like $125 – 135 million. But understand how much estimation there is in here. It’s basically guessing at a rate of decline. It’s making an educated guess on the cost of a win, but it’s guessing at the annual rate of inflation. All the tables you see along these lines — they’re guides. This is ultimately how teams end up determining and structuring contracts, but they’re using some different projections. I think the safe conclusion is that the Cubs didn’t make a wild overpay or anything. Maybe, they wound up a little high, but the math is a lot more promising than, say, the Nelson Cruz math, and the Cubs don’t even need to worry about losing a draft pick. So you don’t have to try to build that value in.

In retrospect, if the Red Sox had offered Lester in spring training what they offered Lester this week, they probably would’ve had him signed. But when Lester was in spring training, he hadn’t yet had his absolutely phenomenal 2014. He rather significantly raised his stock, to the point where he’s more or less deserving of $155 million.

Are the Cubs a good fit?

The Cubs are a good fit. When you’re making a big commitment to a player in his 30s, you’re assuming the real value will come toward the front of the contract. So, these things only really make sense when you’re a team that might be playing for something. The Cubs are no longer a conditional contender. The Cubs are just a contender. They added Lester, another starter, and a catcher in a matter of days.

Steamer. We have to look at it, because we don’t really have anything else to look at. Based on Steamer projections and the depth charts, now, the Cubs rank seventh in the National League in projected team WAR. They’re sandwiched in between the Giants and the Brewers, with the Rockies mysteriously also just ahead. The Cubs don’t look as good as the Cardinals, and they don’t project quite as well as the Pirates, but this looks kind of like a .500 ballclub with massive upside. Projections always come with error bars, and when you have a team with as many talented and unproven young players as the Cubs, you figure the error bars are wider. But while the team still has weaknesses, most of the roster’s been shored up.

Lester’s impact is obvious. Montero’s impact is obvious. Hammel’s impact is obvious. The Cubs might still want another starter, but they already have depth, with Lester and Jake Arrieta forming a cruel 1-2. They could stand to get better in the outfield, but everywhere else is set, generally with depth or some fallback options if the top guy gets hurt or struggles. And naturally, the Cubs’ arrow is pointing up. Lester isn’t joining a team with a narrow, short-term window. There are reasons to believe he should age well, and the Cubs should only get stronger and stronger. So Lester can try to help a contender for several years, instead of for one or a couple.

As it happens, rather conveniently, the Cubs don’t have many other big commitments. Lester’s salary can be offset by the young players getting paid next to nothing for their contributions. Anthony Rizzo‘s under contract forever at very reasonable prices. The same goes for Starlin Castro. Edwin Jackson’s money will be off the books in two years. Montero will be off the books in three years. There’s no question the Cubs can afford this and build around this. And I might as well advance an argument about an intangible: Lester sends a message to the Cubs’ players themselves. Even if they don’t end up in the playoffs in 2015, the young players should be better for their experience in the seasons to follow, and Lester brings an element that wasn’t previously present in the clubhouse.

Now what?

Now the rest of the offseason can happen. Lester was holding up almost everything, even for players seemingly unrelated to the sweepstakes. Teams put together a variety of plans, and now the Red Sox have to go to the plan that doesn’t involve Jon Lester. Same for the Giants. This affects free-agent pitchers, this affects pitcher trade candidates, and this affects outfielders and shortstops and everyone else. You also wonder if this might affect the Reds, causing them to lean more toward stripping down instead of building up.

The Red Sox have options. They’ll presumably re-visit Cole Hamels talks, and they’ll be in to some extent on Jordan Zimmermann, Johnny Cueto, James Shields, and others. Relatedly or unrelatedly, the market’s now been set for Max Scherzer, and you’ve also got Brandon McCarthy floating around. The Red Sox still aren’t in an urgent situation. Neither are the Giants, if they were willing to offer Lester even more than the Cubs. It just becomes a quicker game now. Teams have been preparing for weeks for what they would do after the Lester decision. Now there’s that much less mystery.

That Boston got outbid by so much indicates that they were prepared to be turned down. That San Francisco might’ve had the high offer indicates that they were more all-in on this. There’s maybe a little more concern in the Giants front office. The Red Sox front office is left with questions yet unsettled. The Cubs front office, meanwhile, got to make a signature move. This move broadcasts where the Cubs believe they are to the rest of the league. And maybe the most incredible thing is the Cubs don’t even necessarily need Lester to work out that well, given what else they’ve got. But, imagine what they could be if he’s Jon Lester.