Add up the money they will be paying Heyward, Lester and Darvish compared to the projected production of that trio in 2-3 years, then get back to me about how good they have set themselves up.
Then add in how expensive the rest of their core is going to be.
IDK, if you look at their team the young core is all generally under control for 4 more years (or more). Bryant and Russell are both Boras guys so they will likely continue to go the arby route. Baez and Schwarber might be extended or could go the arby route. One, maybe two of those guys will get traded at some point. My guess would be Baez or Russell and Schwarber gets traded. If they get controllable young talent with those guys then they are likely OK. They've got Contreras, Happ and Almora and have signed Rizzo and Quintana (courtesy of the WS) to nice extensions.
Lester comes off the books in 20 or 21 depending on the option which makes Darvish's 21, 22, 23 seasons less risky from a payroll limitation standpoint. Zobrist is gone after 19 and Chatwood after 20. Morrow after 19 or 20. Quintana after 18, 19 or 20 depending on options (probably 20). Cishek 19, Strop 18 or 19. They've got Hendricks under 3 more years of control if they want it.
Their biggest glaring mistake has been the Heyward mistake (which I said was a horrible contract from the beginning). Unless he opts out, and he won't, they are on the hook for him through 2023 at about $22M per, then they get the joy of paying him his bonus in $5M installments from 2024-27. If anything hurts the Cubs run, it likely won't be the FA contracts they've given pitching but the horrible contract they gave a mediocre offensive RF whose stock in trade was all world defense and base running.
What they
should do is trade Schwarber and Baez for some good young minor league talent that will refill their farm and then be diligent about not raiding the farm over the next 2-3 years. They should also go big on the international FA market while they can.
The biggest thing about their SP is unless Quintana steps up to become a dominant ACE, then they don't match up well with the Dodgers or Nats (or even Arizona right now).