Grade the Trade: ESPN’s unusual Raptors-Damian Lillard swap

The Damian Lillard sweepstakes seems to be heating back up, as the Portland Trail Blazers seem to realize the futility of their situation. The Toronto Raptors might be watching, even if the latest buzz makes it seem like there is no chance of Lillard coming to Toronto.

The latest report from Shams Charania of The Athletic claimed that Lillard would not report to any team that trades for him except the Miami Heat. It’s up to the rest of the league to decide if Lillard’s camp is telling the truth or if he is simply bluffing to force a trade to South Beach.

If Lillard’s stubbornness is all an act, the Raptors could consider going all-in on their current core by trading for Lillard and giving them a roster that could easily come out on top of what is becoming a deeper Eastern Conference. Is Masai Ujiri willing to make such a huge move?

As ESPN points out, such a trade is quite difficult and would require an excessive amount of capital to be sent over to Portland. If the Raptors want Lillard, Ujiri would need to throw their player development-heavy plan for 2023 in the bin.

Grade the Trade: Blazers send Damian Lillard to Raptors for OG Anunoby

Raptors Get
PG Damian Lillard
Trail Blazers Get
SF OG Anunoby
PF Chris Boucher, PF Thad Young
SG Gradey Dick
Two First-Round Picks

The biggest issue in this trade for Toronto would be giving up on Dick, who could be the only first-round pick the Raptors would have under their purview in three seasons. Two more picks would be a tough loss, but it’s also the cost of doing business like this.

Boucher and Young are totally ancillary veterans who could be used more for salary-matching purposes. Anunoby, another impending free agent, is the key. If he signs an extension with Portland, the Blazers might consider accepting this unusual proposal.

A Raptors team with Lillard running point, Gary Trent Jr. and Scottie Barnes on the wings, and a Pascal Siakam-Jakob Poeltl frontcourt would be a hellacious offensive team that could be exactly what Darko Rajakovic needs to run his Mike Budenhozler-adjacent offense.

Losing Dick and the picks would be the most significant objection in this move. Still, the idea of adding Lillard for an expiring contract, getting off Young and Boucher’s deals, and retaining Siakam would make this a reasonably equitable offer that Masai Ujiri would have to consider.

Grade: A-