Just my offseason strategy based purely off emotion right now.
1) $23 million free from Chatwood and Quintana leaving, who combined to play in 9 total games this season. Add an extra $10 million freed up from Lester ($10 million minimum for his buyout) and that's $33 million we can spend on an elite arm.
2) Trade Baez ($12-15 million arb) Schwarber ($10 million) and Bryant ($24ish million arb) if they aren't willing to be realistic about contract negotiations and understand their play this year cost this organization a deep playoff run. Trade them for pitching prospects and let's focus on rebuilding the farm but not rebuilding the big league team.
3) Between $33 off the books for three not-great pitchers and nearly $50 million lost if we trade those three, I absolutely believe we can sign a Bauer, a Semien, and a Lemeiheu all while rebuilding the farm.
For the record, I have always been opposed to trading those three because I believe they deserved every chance possible to make it work in Chicago. However, those three have proved can not help this organization do much.