OK, I think this one can work. The Bulls have hit a hurdle, and they need to make some changes. Could they part with DeMar DeRozan if they get the #6 and #11 picks from Orlando?
This trade is based on a rumor published in Sports Illustrated: Orlando wants Scoot Henderson on their roster (source: https://www.si.com/nba/magic/news/nba-draft-rumors-orlando-magic-trade-portland-trail-blazers-scoot-henderson), but the Trailblazers need talent now. Keeping the #3 pick is not in their best interest if they're going to keep Damian Lillard. The #6 and #11 picks won't help them much either.
So, in my trade proposal, the Magic send their #6 pick and the #11 pick to Chicago.
Meanwhile, Chicago sends DeMar DeRozan to Portland, and the Trailblazers send the #3 pick to the Orlando Magic and Anfernee Simmons to Chicago.
Any suggestions for how to improve this proposal?