Playing around with a google spreadsheet and dreams.
Rotation- Cole, Darvish, Hendricks, Lester, Graveman
Bullpen- Kimbrel, Leclerc, Strop, Ryan, Wick, Wieck/Hulzten, Mills/Alzolay, Maples/Norwood/Mekkes/etc..
C- Contreras, Caratini
INF- Rizzo, Hoerner, Baez, Bryant, Bote, Kemp
OF- Schwarber, Happ, Heyward, Chisenhall, Hamilton/Gore
FA
Cole- $32 million AAV, if he isn't interested you pivot hard to Wheeler.
Chisenhall- $4 million
Strop- $4 million
Hamilton- $1 million
Trades
Quintana for Leclerc. It would be ideal if you add Chatwood and clear as much of his money as possible, if not he goes in a seperate trade.
Salary- $199,410,000
CBT- $209,609,196
I'm not sure which year option getting declined goes to, but I think the Cubs are only on the hook for $4 million. I'd keep Almora in AAA so add another $1 million. That and the $15 million in player benefits would put the Cubs at $229 million + whatever they retained on Chatwood, so there is still money for the trade deadline.