The Bulls go all in on Lillard, trading all available 1st rounders as well as their young wings in hopes that a Lavine-Derozan-Lillard core can turn the Bulls into contenders. The Blazers get a haul that includes several picks and a couple of young wings with some promise. This package improves greatly if Lonzo Ball ever recovers, adding another high IQ player or another useful trade chip.
Trail Blazers:
Receive a package of players centered around the young wing duo of Patrick Williams and Dalen Terry
Lonzo Ball to match salaries, if he ever recovers could be a potential trade peice
Drummond can help fill out an extremely thin center rotation for the upcoming season
A haul of picks including 3 unprotected 1st rounders and 2 2nd round picks
Bulls:
Receive Damian Lillard