History always tends to repeat itself, and in the NBA, it echoes.
Back in 2018, Toronto Raptors president Masai Ujiri stunned the league by trading for a disgruntled Kawhi Leonard, gambling on a one-year rental. All it cost was DeMar DeRozan, Jakob Poeltl, and a boatload of first-round picks.
That move saw them winning it all in 2019 (where they also won four straight against the Milwaukee Bucks after being down 0-2), but considering it cost a franchise cornerstone in DeMar DeRozan and upset their star point guard in Kyle Lowry, it was a move that was ruthless, calculated, and pure Ujiri.
Now, it sounds like he’s watching the same kind of window open again — only this time, the prize is Milwaukee Bucks star Giannis Antetokounmpo.
Masai Ujiri may still be angling for Giannis Antetokounmpo
Per veteran NBA insider Marc Stein (subscription required), Toronto is already expressing interest should the Bucks’ two-time MVP ever ask out. That's not been a secret, of course, but the fact that they're inquiring about the Greek Freak now makes all the difference.
"There have been numerous rumblings about the Raptors' interest in joining the eventual Giannis Antetokounmpo trade sweepstakes … provided that the Bucks' perennial MVP candidate actually asks out of Milwaukee at some stage. Masai Ujiri's affinity for Antetokounmpo is an open secret around the league," Stein wrote on the latest dispatch of The Stein Line.
In particular, it's that last part that matters more than anything. Ujiri has been tracking Giannis since before he entered the league. He famously tried to trade into the 2013 Draft to select him, but couldn’t move up. Since then, that obsession has never really gone away. And perhaps he's finally gearing up to make a move on Antetokounmpo, who just watched the Milwaukee Bucks flounder in the first round of the playoffs for the third straight season.
Of course, as we've been saying ad nauseam now, it really all just hinges on whether Giannis ever becomes available — and right now, most league sources aren’t betting on it. As another insider in Jake Fischer has already reported, what used to be excitement around a possible trade has shifted to skepticism. The consensus? They’ll believe it when they see it.
But that’s the thing about Ujiri: he doesn’t wait for perfect conditions. He moves early, takes risks, and bets on himself and his team. And if this opportunity ever materializes, he won’t hesitate.
It's tough to imagine what a potential Raptors package for the services of Antetokounmpo would even look like. It would certainly have to include Scottie Barnes and a good bunch of first-round picks at the minimum - he's only 23, All-Defense upside, potential multi-time All-Star.
But looking past him, the trade would be tricky. Would Toronto be willing to give up, say, RJ Barrett and Gradey Dick? And would Milwaukee be willing to accept them when teams like Houston and San Antonio likely have better packages to offer?
No matter how it might look like, the point is this: don’t be shocked if Toronto is the team that jumps first. Masai’s blueprint hasn’t changed — just the target.