So let's get everyone's thoughts on next year's roster...
Catcher: Have some depth here but I would guess they stick with the Contreras/Caratini duo unless they get a good offer for either this offseason
1B: Rizzo, nuff said
2B: this could be an opportunity for an upgrade here My guess is they go with a platoon of Happ and others here
SS: Javy, nuff said
3B: See if you can snag a haul of talent for Bryant and go after Rendon in free agency. Even if Bryant stays would not be against still going after Rendon and moving Bryant to a corner OF spot
OF: Basically wide open at this point besides Heyward who they are just stuck with because of his contract. I would not shed tears to see any of them cut or traded and that includes Schwarber. I doubt they will be able to afford Castellanos
SP: Hendricks, Darvish, and Lester are a given to return and I think they pick up the option on Quintana. Would like to see them sign one of the top tier guys but my guess is they go cheap and sign someone that can eat innings and open up that 5th spot for competition with Mills, Chatwood, and possibly Graveman in the mix.
RP: Only guys with guaranteed contracts are Chatwood and Kimbrel. They probably will pick up Phelps $1mil team option and obviously say goodbye to Morrow. I think all UFA's Cishek, Strop, Cedeno, and probably Kintzler all will be gone too. Ryan, Wick, Maples, Mills, Underwood, Wieck, all are under team control. I think most if not all will be retained with many of them headed to Iowa to start the season as depth. Liked what we saw from Hultzen but not sure what his contract situation is. There probably is going to be some money spent on some quality proven relievers with all the payroll coming off the books and the rest of the spots filled in by who does well in spring training.
At this point the only guys I think you can't trade are Javy, Rizzo. Darvish and Heyward won't get traded because of their contracts, Hendricks is going nowhere and neither will Lester at his age and $20 mil for next year and a $10 mil buyout for 2021 plus a full no trade clause. His 2021 has a vested option $25 mil he may not hit now. It would vest if he pitches 200 innings in 2020 or 400 between 19-20 and he only got in 171.2 in 19 so basically Cubs will probably make sure he doesn't get to that 200 inning mark if he looks bad down the stretch again so they have options with him if he comes back another season.