The Portland Trail Blazers have a handful of priorities in a Damian Lillard trade. They want to get back future draft capital, they want at least one prospect to develop alongside their young backcourt, and they want the salary coming back to them to be valuable enough to flip in another deal or to expire after this season. If they can also get off of the contract of Jusuf Nurkic and add a long-term player in the frontcourt, that’s all the better.
This deal checks all of those boxes. It’s not the most lucrative in terms of future picks, but otherwise, this trade brings a lot of value to the Blazers. Jarrett Allen is the ideal defensive anchor to start building around, and Gradey Dick is an off-ball shooter to help unlock the interior games of Shaedon Sharpe and Scoot Henderson. This is a really solid deal for Portland.
Masai Ujiri and the Toronto Raptors are notoriously stingy in trade discussions, making it a difficult proposition to build any trade idea in good faith. Even if this deal is ever discussed in real life, Ujiri will likely walk away. Still, they are the ones who inserted themselves into the Lillard sweepstakes, so let’s examine their role in this trade.
The Raptors get to keep OG Anunoby and Scottie Barnes in this scenario, using Pascal Siakam as the primary matching salary. They would have a core of Lillard, Barnes, Anunoby and Jakob Poeltl, starting either Caris LeVert or Dennis Schroder in the backcourt. With everyone but Anunoby under contract past this season, they can make a run this year and have next summer to continue adding role players around Lillard.
The cost is quite high for the Raptors; they give up two first-round picks, Gradey Dick and an All-NBA forward in Pascal Siakam, albeit one on an expiring deal that they clearly don’t wish to re-sign. If they really want to win the Lillard sweepstakes it may take a deal like this, but it’s a high cost.