Portland Trail Blazers GM Joe Cronin absolutely cooked when he shipped Damian Lillard to the Milwaukee Bucks. The trade has already come full circle, with Lillard returning to Portland where he belongs just two seasons later.
Lillard is adamant that his return is a "basketball decision," as this team is much better equipped for postseason success than the one he left behind. It's largely thanks to the assets acquired in the trade with the Bucks in the first place, and the best part is that Portland has yet to reap the benefits of the entire package: draft capital.
The Blazers acquired the Bucks' unprotected 2029 first-round pick and two first-round pick swaps in 2028 and 2030. Lillard's preferred landing spot at the time was the Miami Heat, but Cronin's decision to bet against the Bucks is about to pay off in a massive way.
Joe Cronin's bet against the Bucks is about to pay off
A Giannis Antetokounmpo blockbuster seems more likely than ever this summer, which would increase the value of those picks. Even if Giannis' loyalty wins out and he decides to stick with the Bucks through thick and thin, it's going to be incredibly challenging to build a contender around their superstar.
They've made desperate moves in an attempt to convince him to stay, continually digging themselves a deeper hole. The most notable example was their decision to waive and stretch Lillard to clear space to sign Myles Turner last summer.
Portland benefited from that decision twice, opening the door for a Lillard reunion earlier than expected while increasing the value of those future picks in the process. Last offseason, CBS Sports' Sam Quinn even ranked the Bucks' 2029 first-rounder as the second most valuable traded draft pick.
After the underwhelming season Milwaukee just endured and the Giannis trade saga picking back up this summer, Portland could legitimately possess the most valuable traded asset in the league now. That could be the key to raising the entire ceiling of their rebuild, whether it's turning those picks into an established star or simply drafting a prospect in 2029.
Blazers are quietly losing leverage in the Giannis sweepstakes
Unfortunately, the relative value of that draft capital has declined, however. The NBA's new anti-tanking rules expand the lottery, flatten the odds, and even punish the bottom three teams with a "relegation zone" that reduces the number of lottery balls for the No. 1 overall selection.
The Bucks are seeking a combination of young assets and draft capital in any Giannis package, signaling their desire to embrace a rebuild. That's the right approach, but this latest lottery change no longer makes it essential for the Bucks to recoup control of their own draft future from the Blazers. While those picks still retain value, Portland suddenly loses key leverage in the Giannis sweepstakes.
To make matters worse, these newest anti-tanking rules are in place through the 2029 NBA Draft, after which the board of governors can decide whether to continue or adjust the system. Right after the unprotected first-round pick finally conveys to Portland.
The Lillard trade itself was a steal for the Blazers, but external factors are suddenly negatively affecting the return at the worst possible time.
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