Can the Cubs Actually Afford to Sit Out the Deeper End of Free Agency?

I can’t tell if recent rumors about the Cubs doing their homework on the elite shortstop free agent market or becoming a likely suitor for Trevor Story or being named the future landing spot for Javy Báez are anything more than a few educated folks connecting some reasonable dots. But I don’t think it’s all that unbelievable. Or, at least, I don’t think it should be.

I still generally believe that short-term, high average annual value (AAV) deals will be the greatest the Cubs actually reach into the market this winter — but consider me on high alert for something more. And, of course, if more reporters join Buster Olney and Mark Feinsand and Jon Heyman in their refrain, we’ll have to start reassessing what we think of the Cubs plans. After all, it absolutely does make sense for the Cubs to be *a* bidder on Carlos Correa, even if they shouldn’t be expected to be the top bidder.

But I also have a nagging fear that it’s all wishful thinking, and that even the short-term route has its flaws. So I wanted to touch on it today, and also try to sort out a bit of conflicting mental energy some of us have been dealing with regarding the Cubs’ offseason plans.

To that end, Patrick Mooney has an excellent write up at The Athletic, wherein he tries to decipher what exactly the Cubs mean when they say they’re going to be really active this offseason, while conceding that they’ll spend only intelligently.

I guess just I don’t see how the Cubs can square these two points from President Jed Hoyer without things working out in a very specific way – one that’s perhaps largely unpredictable and out-of-their-control:

Quote 1: “What we did [during the first rebuild], I don’t think that strategy works in the same way it did before. I definitely want to field a team that’s competitive next year.”

Quote 2: “Now is this our moment to sort of push all-in like we did in ’15 and ’16? I think anyone would look at our roster and say no, right? The time to do that is when you have zero-to-three (pre-arbitration) players that are performing throughout your roster. That, to me, is fairly obvious. You want to wait until that moment.”

So here’s my issue: We keep hearing that this is not going to be a rebuild like last time, but it’s always immediately followed with some version of explaining why now is not the time to spend on big, long-term deals. That time, it seems, can come only after there are a handful of pre-arb players on the roster like there were in 2015 and 2016 … you know, in the immediate aftermath of the very rebuild we’re not looking to repeat. 

So … what gives? How can both things be true?

Well, if you think about it, this paradox is a primary part of what led to our conclusion that short-term, high-AAV deals are the way to thread the needle (the team can be competitive in the short-term while waiting for prospects to graduate before THEN spending on the monster long-term deals), but that doesn’t feel like something you can promise fans, *especially* not without a rebuild. It’s not like you can be certain you’ll land everyone you want on that type of deal.

Short-term, high-AAV deals have been rebuffed often by free agents in recent years because, while the high AAV sounds nice, most would rather lockdown the largest guarantee possible when they have a chance. Sure, some guys are willing to bet on themselves, hoping to earn another crack at free agency for a greater overall take, but others don’t see the point when there’s a better, more secure offer on the table right now. And moreover, the continued ubiquity of opt-outs in most major deals reduces the desirability of shorter term swings in the first place. Free agents can basically have their cake and eat it too (albeit at a slight discount).

This means, as a plan, you may not be able to get the guys you really want if you’re artificially limiting your pool to only those guys who will accept this kind of contract. So unless the Cubs have some alternative in mind that they’ve kept very quiet, I’m concerned this plan of attack is at risk of leaving them empty-handed come spring, all under the guise of wanting to spend intelligently. Recall, we are interested in seeing the Cubs go this route *IF* they can successfully target and land their preferred free agents early, and not solely pick from the leftover pool like last year.

Let me put an even finer point on that.

I’ll take no issue with the Cubs if they aggressively attack the short-term free agent market this winter – *landing the guys they want* – but ultimately come up short in competitiveness 2022. Because there’s a lot I like about that approach for the Cubs right now, and I respect the idea if they can pull it off. That’s where I’d have some grace. For example, if the Cubs go out and top the market short-term for a group of guys like Noah Syndergaard and Jon Gray and Jorge Soler and Marcus Stroman (these are just examples), but the Cubs do not stay competitive through July and have to sell off again, well, okay, at least they did actually execute on the strategy (while waiting for lower level prospects to emerge and a more obvious time to spend), and maybe got some more prospects for their trouble. That’s one thing. I can tolerate it.

But if they go this route and don’t actually even wind up SIGNING their preferred targets, sticking us with leftovers and second-choices? That is entirely unacceptable. That’s where the offseason would be a failure, and we should not have grace for a terrible 2022 Cubs team, if it comes to that.

And that’s why the short-term, high-AAV plan scares me a bit. It would leave so much out of the Cubs’ control due to artificial limitations of spending intelligently. You’re trying to squeeze yourself into a very narrow window of players who might simply not be into it, or who will prefer to go elsewhere. The Cubs might have to be a little more flexible in the range of contracts they would consider this offseason. Maybe someone gets two years instead of one. And another guy gets four years instead of three. And maybe you at least hold yourself open to the possibility of the right six+ year deal.

Moreover, I don’t think the shortstop rumors we’ve been hearing should be all that shocking. The Cubs are a major market team with a ton of room in their payroll, a glaring hole at shortstop right now, and no top prospects anywhere close to MLB. Why shouldn’t they be involved at least at some level?

So at the end of the day, with so much payroll space available (and so many dollars saved at the deadline), I think I want to be a little more specific about what I’m saying: If the Cubs want to be competitive next year and avoid another rebuild by taking matters into their own hands, then the spending this winter might have to be more aggressive than strictly intelligent. Otherwise, there’s a risk of being right back in the same spot come Spring Training.

Brett Taylor contributed to this post.