The Raptors are currently stuck in a middle ground with a level of talent that’s neither competing for a championship nor generating good lottery odds. Most expect them to enter a full rebuild by dealing their top-end players, yet that hasn’t come despite missing the playoffs last season.
They could instead push their chips in for Lillard despite the 33-year-old’s reported unwillingness to head anywhere outside Miami. Let’s have a look at how a three-team deal could play out between the Raptors, Trail Blazers and Warriors.
Pairing Lillard with Pascal Siakam and Scottie Barnes is an intriguing trio, plus they keep their starting center in Jakob Poeltl. Anunoby, Trent Jr. and Boucher are all key members of their rotation, but they get Gary Payton II back and are undoubtedly better and more dangerous after this trade.
Toronto do mortgage their future by dealing a 2027 and 2029 first-round pick — a risk given Lillard’s likely unhappiness at heading to Toronto. Still, it’s what they’d have to do to get Portland interested.
A talented scorer, genuine backup big, two young former lottery picks, and two future first-round picks is a fairly good haul for a player who desperately wants out. Portland could on-trade Trent Jr. and Boucher to contenders for further assets, while Kuminga’s development is probably the key to this deal.
The Trail Blazers could safely assume Lillard won’t be in Toronto by 2027, meaning there’s a genuine likelihood that the two first-round picks both convey in the lottery.
After backing in their veteran core and taking a win-now approach this offseason, the Warriors dive even further into that mindset by moving their two recent lottery picks, and Gary Payton II, for O.G Anunoby and a second-round pick from Toronto.
It’s probably too much to give up for Golden State to consider, but they did have serious interest in the 26-year-old at last season’s trade deadline. The decision would also hinge on the chances of Anunoby re-signing with the Warriors — perhaps unlikely given he’d be the sixth or even seventh-man in the rotation.