The team that has worked its way into the Damian Lillard conversation in recent days is the Toronto Raptors. They have an ill-fitting collection of frontcourt players and a desire to win now rather than enter a rebuilding season. That could lead them to push the chips in to add Lillard to replace the departed Fred VanVleet.
The issue for such a deal is the package going back to the Trail Blazers. Portland wants young players and draft picks as they look to build a great team five years from now, once players like Scoot Henderson and Shaedon Sharpe are entering their primes.
Yet if the Raptors don’t want to move Scottie Barnes they almost certainly need to send Pascal Siakam or OG Anunoby, two veteran players who can both hit free agency next summer and will be quite expensive to re-sign. Why would Portland want to commit to such a player?
Enter a third team like the Cleveland Cavaliers, perfectly positioned to help make this deal happen. Here is what a trade could look like:
The Toronto Raptors get their man in Damian Lillard, take on the salary of Jusuf Nurkic as a backup center and add Caris LeVert as a useful ball-handling Sixth Man (or even starting shooting guard). The Cleveland Cavaliers flip Jarrett Allen, Isaac Okoro and LeVert for Pascal Siakam and Chris Boucher, a rangy shot-blocker to fill out their frontcourt depth. The Portland Trail Blazers land a large haul of players and picks, with everyone on an expiring deal except for the young defensive anchor in Jarrett Allen and the rookie lottery pick in Gradey Dick.
Does this deal make sense for all sides? Let’s grade this trade for all three teams involved.