The Portland Trail Blazers traded superstar Damian Lillard to the Milwaukee Bucks in the summer of 2023. Just two years later, Lillard shockingly returned to Portland. Due to the deal, the Blazers are now armed with valuable assets, and somehow still managed to get Lillard back shortly after. Even before seeing how Milwaukee's future picks they owe Portland pan out, it's safe to say that the Blazers are the clear winners of this lopsided deal.
The Bucks made an all-in move to pair Lillard with Giannis Antetokounmpo in a three-team deal involving the Phoenix Suns. Here were the details of that trade:
Bucks received: Damian Lillard
Trail Blazers received: Deandre Ayton, Toumani Camara, Jrue Holiday, 2029 first-round pick (via MIL), two first-round pick swaps (via MIL, 2028 and 2030)
Suns received: Grayson Allen, Keon Johnson, Nassir Little, Jusuf Nurkic
Bucks continue to make Damian Lillard trade better for Portland
On paper, Milwaukee was built to contend for another championship. But the theoretical dream pairing of Lillard and Giannis didn't translate to on-court success, at least relative to expectations. Lillard and Giannis both dealt with injuries throughout their two seasons together; they also came at the worst time, resulting in two disappointing first-round playoff exits.
Even when the duo was healthy, though, they never seemed to be fully in sync with one another. A fully healthy Bucks roster still wasn't built to contend, making it clear that their all-in trade for Lillard backfired.
To make matters worse, Lillard suffered an Achilles tear in Game 4 of their playoff series against the Indiana Pacers. The fallout was that everyone closely monitored the situation surrounding Giannis and whether or not he would request a trade to free himself from this crumbling roster. Giannis is one of the most loyal superstars in the league and has shown no indication of requesting a trade out of Milwaukee (up until this point). However, this situation still forced the Bucks' hand because they needed to seek immediate roster upgrades.
Lillard is expected to miss the entirety of the 2025-26 season as he recovers from injury, making it more challenging to convince a 30-year-old Giannis to essentially waste a year in his prime while he patiently waits for Lillard to return. Not to mention, questions surrounding whether a 35-year-old Lillard will even return to form following such a brutal injury. This ultimately led to Milwaukee's decision to waive and stretch the remaining $113 million on his contract over the next five years to clear enough cap space to sign Myles Turner.
The issue with this desperate move by the Bucks is that Turner isn't a needle mover to get them back to contention. He just averaged 10.6 points, 4.4 rebounds, and 1.4 assists in the NBA Finals. If I'm Giannis, I'm in the locker room thinking: this is who we sacrificed our long-term financial flexibility to replace Lillard with?
Milwaukee's desperation to keep Giannis happy in the short term is the very thing that could ultimately drive him away, as their ceiling is limited. The Blazers' front office should just be sitting back in a recliner with a big bag of popcorn while they watch the Bucks continue to collapse, increasing the value of the picks they owe Portland.
Cronin's bold bet against a Giannis-led Bucks roster is paying off better than anyone could've expected.