Step 2: Let DeMar DeRozan walk
This would be tough, but it’s the bed the Bulls made by not trading him at the deadline when they could have reaped some kind of assets. DeRozan is still good and he’s durable, so re-signing him does make some sense, but less so if you are rebuilding.
Letting him go for nothing would be painful, but not as painful as paying him upwards of $40 million a year when he is 37-38 years old, sacraficing a lot of financial flexibility in the process. Even if you could get him on a shorter deal worth say 3 years/$90 million, you’d essentially be committing to this same group only older, now paying the luxury tax and with no room to make additions.
Trading LaVine into someone’s cap space without taking a big contract back and letting DeRozan walk would be a crime of asset management, but these two are now sunk costs and throwing good money after bad just makes it worse. The Bulls now have upwards of $70 of cap space to play around with.