The Chicago Bulls would run away
The Bulls have made it clear that they have no intention of tearing down their roster this offseason, and this is the kind of move you would make if you were going to rebuild, not try and compete.
I would bet heavily against the Bulls making this type of trade, even though it is one they should consider.
They’d get off of two years of LaVine’s salary, plus recoup some valuable draft assets that the Bulls desperately need. They don’t control their own pick outright until 2028 because of the one they owe San Antonio and the pick they are owed from Portland may never convey, as it is lottery protected and turns into a second rounder in 2028.
Gaining two 1st-round picks would allow the Bulls to make bigger trade offers in the future, and after this season they’d have a whopping $40 million in cap space to play around with at least.
The problem is that the Bulls seem to be content chasing mediocrity when they should probably sell off their veteran assets for all of the young players and picks they can get. Instead, the Bulls will probably re-sign DeRozan, allow Caruso to play out his final year and potentially lose him for nothing, fail to trade LaVine and bring back Patrick Williams.
If all of that happens, expect to be right back here next season. Trading for Simmons would be the kind of desperate move the Bulls never make, even if there is some sense to it.