This can't happen until January 15th at the earliest, but here's my thinking. We get some added depth, scoring and defense all in one (three) fell-swoop(s):

Blazers out: Ant, Hart, Little, Winslow, Keon, GB3, John Butler Jr., three 1st Rounders

Blazers in: Lou Dort, Lauri Markkanen, Jordan Clarkson, Goran Dragic, two 2nd Rounders

OKC out: Lou Dort

OKC in: Hart, Keon 1st Rounder

Jazz out: Lauri Markkanen, Jordan Clarkson, 2nd Rounder

Jazz in: Ant, Little, Winslow two 1st Rounders

Chicago out: Dragic, 2nd Rounder

Chicago in: GB3, JBjr. 1st Rounder Restrictions lifted

Blazers starting 5: Dame, Dort, Grant, Markkanen, Nurk

Blazers bench: GP2, Dragic, Clarkson, Sharpe, Watford, Eubanks, Walker, Badji...etc.

Why everyone does it:

Blazers desperately need depth and defense. Dragic would make for a great veteran backup PG, ready to run the show, not give away games and he brings back a 2nd. Lou Dort makes the perfect running mate for Dame, being a Top 10 defensive player in the league who puts up good numbers and plays well above his 6'4 frame (7'0 winsgpan). He's under contract for the next 4 years and is only 23! Clarkson is the exact sort of 6th man/spark plug off the bench you need to keep you in games and can go super nova at any moment. He and GP2 will wreck most the leagues 2nd units. He's a savvy vet, and brings a confident winning swagger to the bench. Something we currently don't have. Lauri Markkanen is a big, young PF, with tons of upside. He moves Grant to SF, increasing he overall size of our starting 5, and replaces all of Ant's offensive output while adding defense. Portland saves about $200K in salary, so upper management can't complain. This is the exact sort of consolidation trade the team is looking for, we get immediate impact players and keep Sharpe. Fill out the roster with 10-Days and call it a day.

OKC is nowhere near done with their rebuild, and stacking picks is their way to the promised land. Hart provides some great veteran leadership for the couple of weeks he'll be there, and additional salary cap, before they flip him again for another 1st to a playoff contender. So OKC essentially trades Lou Dort for two 1st Rounders... quite the haul for a shooting guard.

The Jazz blew it up to rebuild and make a run for Wemby. So far they aren't doing a very good job of it, due to Lauri and Clarkson. They were definitely brought in to be trade bait later on, and now is the time to move them while their stock is hot and the Jazz still have a chance to torpedo the season. The Jazz get two 1st's as well as some youth in Ant and Little and also lose about 15 points per game (L&C = 43/g, A&L&W = 30/g), ensuring they lose more games this season, while not overtly tanking and adding more youth. And Winslow's contract is off the books at the end of the season, or they can look to flip him.

Chicago wants the best possible odds on their pick, and Dragic is not on any of their timelines. In all honesty, Chicago is probably looking to blow it up pretty soon. So getting the best odds on your 1st Rounder makes sense and some young guys for the rebuild, or to be used as cannon fodder in future trades. I'd rather not include any players, but because of our salary cap, we gotta move a couple guys so we don't take on $2m this year.