A Well-Articulated Take on How and Why the Cubs Will Spend This Offseason

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A Well-Articulated Take on How and Why the Cubs Will Spend This Offseason

Chicago Cubs

Embedded within Jed Hoyer’s comments on the Cubs being both “really active” and “intelligent” in free agency, I got the sense that the team’s approach to free agency is gonna look something like this: a lot of shots on shorter-term, higher-risk, high-upside players. The kinds of guys who get $8M to $20M annual value, but on only one or two year deals. The kinds of guys for whom you’re paying a premium because they could be studs, but who come with health/age/production risks. The kinds of guys you can offer a starting job to, but whom you definitely have to woo with the higher AAV because you might not be an obvious contender.

It’s just a sense I have about what the Cubs are going to do when I consider the finances, the competitive cycle, the state of the roster, the best levels of the farm system, and so on.

There are a lot of ways to describe that sense, though, and I thought Sahadev Sharma offered up an excellent variation in his latest Q&A. He focused on contract value, competitive timelines, and being honest about your chances in a given season. Even when those chances aren’t zero – and they should just about never be “zero” again for the Cubs – they aren’t always high. And that impacts how you should operate if you’re a team like this year’s Cubs:

That said, though, the Cubs will spend this winter. Including some rough estimates with arbitration-eligible players, their payroll commitments for 2022 should be in the $70-80 million range. They should easily be able to double that (if not more, but let’s be conservative), which gives them quite a bit to spend.

But, let’s also take a look at how the Cubs probably view their situation. How likely are they to contend in 2022? Even if they sign one player they feel will perform at an All-Star level or above and a few other “value” deals, it’s still in the 10 percent area. Then in 2023? Maybe 30 percent?

So what’s the true value in signing a player to a five- or six-year deal this offseason? When handing out long-term deals (basically, anything over three years), front offices generally feel like the best value will be gained in the first half of the deal. Anything on the backend is almost considered a bonus.

So in this scenario, the Cubs would be signing a player to a long-term deal and would have a low chance of competing on the front end of that deal. Then, two years from now, when Brennen Davis could be an All-Star and players such as Jordan Wicks, Kevin Alcantara, James Triantos, Owen Cassie and others are in the mix, instead of having money to spend, Hoyer’s hands are tied because he’s got $25 million invested in a player he signed two years ago who’s showing clear signs of aging and deterioration in production.

On a very long-term deal, you’re going to get the best years right at the start, when that player might be least valuable to a team in the Cubs’ spot. And since competing is a zero sum game, you do have to think about when you can maximize your shots – when you can take a 60% shot at a deep postseason run and turn it into a 70% shot, rather than when you can take a 10% shot and turn it into a 20% shot (and hurt your future 60% shot in the process). It’s just another way to think about the timing of particular types of deals. I found it well-put.

And importantly, it’s NOT a point about not spending at all. It’s just about the types of targets you pursue, because the Cubs do have plenty of money to spend. They just have to spend it well.

As Sharma notes, of course you could also just hope that the Cubs sign tons of long-term, impact guys immediately, and keep spending more and more to never have to worry about the compounding effect years down the road (i.e., never worry about spending “well”). If you want to bang that drum, go ahead and bang it. I am of the mind that the Cubs simply aren’t going to carry a $350+ million payroll in 2025, though, so I come at it from the perspective of wanting the front office to be mindful of those longer-term issues (otherwise, because of the reality of the budget, you get into a spot where you have multiple years of significant payrolls, but no ability to make meaningful additions … as we saw the last few years).

Author: Brett Taylor

Brett Taylor is the Editor and Lead Cubs Writer at Bleacher Nation, and you can find him on Twitter at @BleacherNation and @Brett_A_Taylor.