No. 2: Michael Porter Jr.
The Denver Nuggets are a championship contender. They proved they can win it all just over a year ago, they have the best player in the league, and their core is largely intact from that title run. At the same time, the Denver Nuggets are also pinching pennies, making cost-cutting moves to manage their payroll, including letting Kentavious Caldwell-Pope walk in free agency a year after Bruce Brown walked away.
If the Nuggets want to both try to win while opening up financial flexibility, trading Michael Porter Jr. for Bruce Brown and Kelly Olynyk is a legal trade that would give Denver a significant amount of breathing room moving forward. Brown could step back into his old role or even move into the starting lineup in place of KCP. Olynyk could fill much of the role Porter Jr. is currently filling as a stretch-big next to Nikola Jokic.
The Raptors, on the other hand, would be taking a flier on one of the league's best pure shooters, a dynamic scorer in Porter who would be an ideal pairing with Scottie Barnes in the frontcourt. The onetime Missouri forward is a career 41 percent shooter from 3-point range and would open up the court for Barnes to work inside.
Who should be compensating who in this deal? On the one hand, Porter Jr. is a dynamic scoring forward who seemed worth a max contract to the Nuggets just a few years ago and started on a title team 14 months ago. On the other hand, he is clearly overpaid on that deal, which will pay him another $115 million or so over the next three seasons, while Brown is on an expiring deal and Olynyk has two years left at $12 million or so per year.
Given the size of Porter Jr.'s contract, it's likely the Nuggets would need to append a small asset to his deal, be that a wobbling prospect like Jalen Pickett or a second-round pick. This is a fascinating challenge trade that could work out for both sides.