This is a dream scenario for the Chicago Bulls but there are problems
If the Bulls can get off their two worst contracts AND get Brandon Ingram in the process it is an absolute no-brainer for Chicago, which makes me doubt it could ever happen.
The picks involved aren’t much to give up for the Bulls, as the Portland one may never convey as a first-round pick anyway and the other two are distant second-rounders they can replenish in other ways.
Ingram is young enough to fit in with the core and Wiggins at least provides depth as a 3-and-D wing. The Bulls might be able to compete with a young team that would have plenty of future financial flexibility.
The caveat is that they potentially end up with zero draft picks in 2025, as they’d be giving up the pick from the Trail Blazers and may be just good enough to have to give away their own top-10 protected pick that they owe to San Antonio.
Having no draft capital in a loaded draft class would be a high cost to pay to get off two contracts and take on a guy on an expiring deal who could just leave after next season. But it speeds up the rebuild either way, as the Bulls are rid of LaVine's albatross contract and would have a ton of cap space if Ingram did decide to go somewhere else.
It’s not perfect for Chicago, but the trade solves two of their biggest problems, keeps them competitive for the short term and opens up some better future possibilities.