No. 2: Jaylen Brown
By far the best player on this list, Jaylen Brown is the kind of two-way wing that you send assets out to acquire, rather than receiving assets to take him on. Yet the reality is that Jaylen Brown signed the largest contract in NBA history last offseason and is on a team that has a tremendous amount of money committed to its core players.
If the Boston Celtics lose early this postseason they will need an avenue to make changes, and the second luxury tax apron will prevent them from doing much of anything unless they get off of money. Most trade partners who would be interested in Brown would need to match most, if not all, of his $49.7 million salary for next season.
Enter the Toronto Raptors, who could absorb nearly all of Brown's salary. That would likely significantly reduce the cost of acquiring Brown, giving the Celtics enough breathing room on the salary sheet to make another move. The Raptors could also include a veteran or two depending on what the Celtics want; would Bruce Brown on an expiring contract interest them? A Kelly Olynyk reunion to replace Al Horford?
Jaylen Brown could immediately pair with Immanuel Quickley and Scottie Barnes to form a formidable two-way trio of young stars, with Brown as the established veteran with an awful lot of pedigree. The Raptors would need Scottie Barnes to become a Top 10 player to be a true title contender with that core, but it's a tremendous starting point, and they could likely add Brown at a discount by giving the Celtics such salary relief.