Neither the Cubs nor Cardinals has a great outlook moving forward.
The contracts are probably the big thing in all this. It hinders flexibility in who you choose to retain, and who to choose to bring in.
The Cubs have roughly $42M available right now BEFORE arbitration. You're gonna let Morrow ($12M) walk for certain - all other club options except Rizzo/Quintana let go free up another $7M. You're gonna drop off Zobrist, Hamels, Castellanos, Cishek, Strop, Kintzler - all possibly gone. 3 to 5 of those are gonna hurt.
Hamels leaves a gaping hole in the rotation. And if Darvish ($22M) walks, while you gain much needed space, it's another gaping hole.
I'm betting, given the arbitration (Contreras, Bryant, Baez, Schwarber) coming - they're gonna try very hard to deal Heyward and Chatwood.
The Cubs FO has a very chaotic winter coming.
The Cardinals are in much better shape by comparison. However as mentioned, a lot of it is tied up in older players who are declining. Carpenter, Fowler and Molina...yikes ($55M total). But they're sitting at $146M for 2020 at the moment and only have John Gant for arbitration. They got about $70M to play with, with only the currently dead money of Brett Cecil a complete waste (drops off after 2020).
They've got Wainwright and Ozuna as key FA's. Wacha and Wieters are probably gone. I believe Ozuna walks because there's OF's galore in the system (Dylan Carlson is the name to remember). Wainwright may be reasonably cheap to retain. The fans believe Wacha is gone but I am not so sure, he also may be cheaply had (benefits of his bad year) and he's insurance if you aren't all in on rookie replacements. And a return to health of Reyes, Gomber etc would certainly mitigate the need (versus the desire) to go all in for a Gerrit Cole.
And if Carlos Martinez can return to starting, all the better. The bullpen can absorb losing him given Giovanni Gallegos' ascension, and the depth guys like Miller, Gant, Brebbia, Fernandez, Webb, Helsley, Ponce de Leon et al provide. The bullpen is deep and mostly all locked up barring injury.
They have cheap internal options, but few high end cheap options save Carlson (who might be a half-year away yet). Yes, the system isn't deep currently with high end guys nearly ready, but they have somewhat useful options that the Cubs don't really have. And it's reasonable to assume maybe Wainwright, Fowler and Carpenter might have one more decent season in their tanks (just be average), with Goldschmidt rebounding somewhat. Molina...2020 will probably be his swan song given Knizner's presence. Father Time appears to have made the kill finally with his bat (yet, we got a guy ready to go to replace him), but he's still serviceable behind the plate. But the recent injuries have finally (I believe) caught up with him.
Troubling (the pitching depth got a hell of a lot thinner this year)...but not the end of the world. I can see a very similar roster come April 2020, but I don't see them falling off a cliff. They need upgrades/rebounds more than having gaping holes to fill. But yeah, a Gerrit Cole would be awful nice to slot in the rotation and they will definitely check in hard on him.