Making a trade call between these two teams more interesting is the fact that Chicago owns Portland’s 2024 first-round pick. Trading the pick back to the Trail Blazers (which is protected through 2028) could be a strong way to begin negotiations.
But after that, it gets dicey. Zach LaVine is a big name but, like Lillard, is owed a lot of money for the foreseeable future ($178 million over the next four years). He also offers the same redundancy issues as Tyler Herro, but older (28) and for more money. The Bulls would have a hard time trading LaVine for neutral value at this point, let alone for a star like Lillard.
Patrick Williams is at least an interesting flyer but, at this point, that’s what he would be. Though he’s only 22, Williams has averaged 9.7 points and 4.3 rebounds over his three-year career, and has yet to emerge as the lockdown defender many thought he would be when Chicago picked him fourth overall in 2020. He will be a restricted free agent after the season, so Portland would have to make a decision on him soon. Williams is far from a blue-chip prospect.
As for picks, Chicago’s firsts are tied up through 2027, so they can only offer a 2029 first-round pick unless they adjust protections to the 2025 first they owe San Antonio.
All in all, this isn’t enough to get it done.