Damian Lillard surprisingly returns to the Portland Trail Blazers after spending just two seasons in Milwaukee. The Bucks made an all-in move to acquire Lillard, which was an overly aggresive decision that backfired as it resulted in consecutive first-round playoff exits. This offseason, Milwaukee compounded that mistake and sacrificed even more of its future to Portland's benefit.
Blazers continue to capitalize on Bucks' impatience
The Bucks decided to waive and stretch Lillard's remaining $113 million over the next five seasons. Milwaukee has this pressure to win now with superstar Giannis Antetokounmpo (while he's still on the roster) and waived Lillard to clear enough cap space to sign free agent Myles Turner to a four-year, $108 million deal. However, the Bucks' urgency to upgrade around Giannis could ultimately be the very thing that winds up driving him away.
Turner just averaged an underwhelming 10.6 points and 4.4 rebounds in the Finals. He's not going to be Lillard's replacement in terms of being a co-star for Giannis. He's also not a needle-mover for Milwaukee, even in the depleted Eastern Conference. Now, the Bucks have to pay a departed Lillard and a talented but limited Turner substantial long-term deals, which limits their flexibility to upgrade their roster and get Giannis the pieces he actually needs to win another ring.
The Blazers are well-positioned to capitalize on the Bucks' downfall in more ways than one. Portland already won the initial blockbuster Lillard trade, as they managed to receive building blocks Toumani Camara (directly) and Deni Avdija (indirectly) because of this deal. They also have extremely valuable draft capital in Milwaukee's 2029 unprotected first-round pick as well as swap rights in 2028 and 2030.
With Lillard out of the equation physically but not financially, those picks should only increase in value. That's also not even accounting for the possibility that Giannis ultimately decides to continue his career elsewhere, which would then make Milwaukee's picks some of the most valuable draft capital in the entire association.
The Bucks have now made multiple myopic moves as they desperately attempt to keep Giannis around, and the Blazers have wisely been around each time to capitalize on that impatience. Blazers general manager Joe Cronin's bet against the Bucks, who were coming off a recent championship and have a top-five player in the world still in his prime, was bold. And fortunately for Portland, that gamble is about to pay off in a major way.
This was a rare full-circle move for Portland. They were able to trade Lillard at peak value, strategically flip those assets to help shape their rebuild, and then bring back Lillard on a team-friendly deal. At 35 years old, he won't be the player he once was coming off a brutal Achilles tear. But the Blazers don't need him to be -- they already won this trade. Anything they get from Lillard should be considered icing on the cake.