Do We Finally Understand “The Plan,” Chicago Cubs 2020 Edition?

Admittedly, before I really dug in on the near and long-term costs associated with consecutive years over the luxury tax, I did not believe the $208 million luxury tax level in 2020 would be a guiding principle for the Cubs’ offseason. I let my gut sense of “should” get in the way of actually digging into and synthesizing the available information.

Even before I researched the CBA more thoroughly for luxury tax repeater implications, there were signals that the luxury tax was going to be a hard line in 2020. There were hints from Tom Ricketts and Crane Kenney in radio interviews. There were implications from the Cubs’ rumored activity. There was the fact that the Cubs were pretty darn close to the luxury tax limit already. There were those reports that the Cubs told agents they couldn’t do literally anything until they first moved out some salary.

I saw it all. We covered it all. And still, I was convinced that a few million extra bucks weren’t going to be the difference between the Cubs fielding a good team in their window and once against leaving exposed huge cracks. They just couldn’t let that happen again after a relative disaster in 2019.

Except maybe that relative disaster is precisely why the Cubs are more willing to expose cracks in 2020 in service of longer-term goals? Some noble, some less so?

Could I really still think the luxury tax was not going to be a target after I really dug in on the costs, for the Cubs, of being just a dollar over that $208 luxury tax limit in 2020? And the exponentially larger costs of being over the luxury tax for a third straight year in 2021? After I more deeply considered the way the CBA really, really pushes big market teams not to keep going over the tax in many consecutive years? When I considered some of the roster reshaping the Cubs want to do for 2020 anyway? When I think about everything Theo Epstein said that suggested the goal of this offseason is about ensuring the club doesn’t fall off a cliff after 2021?

And when I remember all those other signals that I decided previously to ignore?

Yeah, I now think the Cubs’ preferred approach has become pretty clear. Sometimes, all you have to do is really listen.

Call it “The Plan,” circa 2020:

1. Trade away pieces that have huge value to aid in 2021 and beyond, and also to diversify the lineup.
2. But also focus on trading the guys who have a large enough salary that it could get the Cubs under luxury tax in 2020 to reset penalties.
3. Sign cheap, short-term pieces to fill any gaps and hope that one or two surprise to the upside.
4. Try to compete with what you have, but hold the bar a little higher on what “competitive” looks like come June and July.
5. If it’s not a huge lead in the division, sell off some more with a particular eye on pieces that would help as soon as 2021.
6. With luxury tax penalties reset, proceed with the flexibility to have a “normal” offseason after 2020 in order to compete in 2021 and beyond.

It’s not quite a “The Plan”-scale, multi-year rebuild, but it’s something we’ve seen other large market teams approximate with success (Yankees in 2016), and the synchronicity of the money and the roster needs reminds me of spending (well, not spending) during the original rebuild. So, it’s like a rebuild-lite. The 2020 Plan.

I think for me, I can see the baseball merits of the plan, particularly with a flawed team that is coming off an 84-win season and – without significant changes at a significant cost – is unlikely to be the kind of 92ish-win team on paper that you’d want to see heading into a competitive season. If you think your median projected outcome is 82-84 wins in a competitive division, but you think you can set things up to be much, much better than that in the years ahead, it’s not like punting on a season is a new strategy. Heck, it’s barely controversial anymore.

However, that kind of plan, when you’ve got two years – and only two years – of so many prime-age players under control is fraught with risk. There are no guarantees that you can turn Kris Bryant into a younger, cheaper Kris Bryant. There are no guarantees that you can land the free agents you want even when you turn the hose back on (and you freaking better turn it back on in 2021 if this is the plan, Cubs). There are no guarantees that you won’t suffer a series of injuries and underperformance (like in 2018) that totally wreck your plans to make future trades to support the post-2021 window. There are absolutely no guarantees that the roster in 2022 will look better than the roster today.

The question is how confident are you that you can get loads and loads of talent in trades right now, *AND* do a much better job developing what you’ve already got over the next two years? If you are the front office, and you think you’re going to be able to get a crapload for guys like Kris Bryant and Willson Contreras, and if you think you can get some nice pieces selling off at the deadline, and if you think you can ball out on development from there, then sure, I could see actively wanting to punt on 2020 without even considering the money. And if ownership is like, “Yeah, we’re not gonna keep supporting big spending over the luxury tax because doing it lots of years in a row costs us exponentially more money,” then maybe the front office says, OK, let’s punt on 2020 for the baseball reasons, but also because we can get more to spend next year if we do – and we’ll be all the better in 2021+ for doing it.

Again, this is all theoretical. I can see the arguments, even if no one has actually made them. We’re having to do a whole lot of thirdhand extrapolating, but I’m pretty sure I’m right at this point.

But is it a *good* approach? Is it what the Cubs *should* be doing?

I’ve long said I was on board with a dramatic roster reshaping in service of more diversity in 2020 and better chance at contention after 2021. But I always paired that with the idea that a big-market team like the Cubs should also be able to sign some nice short-term pieces to help in 2020. From everything we’re seeing, that second part is not going to be doable, because it would keep the Cubs over the luxury tax for a second consecutive year (and a third consecutive year in 2021 if the spending never came down). Based on my research yesterday, I really don’t think the Cubs are going to put themselves in a position to be over the luxury tax three years in a row in the current CBA. It’d be nice to be wrong on that part, but, again, I’m pretty sure I’m right.

So, then, I’m left feeling pretty ambivalent about all of this. I know that there’s a chance the Cubs could still compete in 2020, even after all this maneuvering and cost-cutting, but let’s be real: it’s a punt. Competing in 2020 would be a happy byproduct of The 2020 Plan’s moves, not the primary active goal. When money, alone, might have bridged that gap? It’s hard for me to celebrate this plan with a whole heart.

On the flip side, I concede that I do agree with the baseball side of The 2020 Plan, because there are huge chunks of the roster that scare me in a tight division, and I definitely don’t want to see the Cubs fall off a cliff after 2021. There are versions of Kris Bryant and Willson Contreras and whoever trades that make sense to me in the bigger picture, purely from a baseball – i.e., non-financial – perspective.

It think what ties this together for me – or, more accurately, the chokepoint where I get hung up – is not knowing what the spending plan is for 2021. If I knew, for certain, that the Cubs were thinking they’d spend aggressively (or at least without the ridiculous limitations) after 2020 – new TV deal in place and all that – I’d feel much more on board with The 2020 Plan.

As it stands, I’m left somewhere in limbo: understanding parts of it, questioning parts of it, and unable to come to any kind of firm conclusion until some of the things about which we’re speculating actually happen.