Giannis Antetokounmpo didn't want to leave his family, home, and community that he established in Milwaukee during his time playing with the Bucks. But he also realized that if he wanted a chance to contend, he would have to play elsewhere.
It was a similar dilemma to the one Damian Lillard faced when he requested a trade from the Trail Blazers in 2023. But now Giannis is the one figuring out for himself that the grass isn't always greener.
There's still plenty of time for Giannis and the new-look Miami Heat to turn things around, but this team is 2-5 to start the season. Barring a drastic move before February's trade deadline, this doesn't seem to be a contending roster. It makes you wonder whether this was even worth Giannis leaving that all behind in Milwaukee.
Lillard certainly realized that it wasn't, returning to Portland just two seasons later. But it's not a simple black-and-white comparison between the two, in part because of the trade returns.
Blazers’ Damian Lillard trade came full circle in a rare way
Lillard was adamant that returning to the Blazers wasn't just rehabbing close to family, but also a "basketball decision" to win games. We're seeing that decision pay off early for the 5-1 Blazers, where Lillard seems like the ideal fit for last season's floor-spacing issues.
But this was still a playoff team last season even without Lillard, and that was in large part thanks to the trade that sent him away in the first place. He joins an All-Star in Deni Avdija, an elite 3-and-D piece in Toumani Camara, ascending rim protector Donovan Clingan, potential Sixth Man of the Year Jrue Holiday; the list goes on.
The same wouldn't be said should Antetokounmpo want to come back to the Bucks in a few years. They owe future draft picks to the Blazers and a few other teams as well. They also still owe Lillard $22.6 million annually after waiving and stretching the remaining $113 million to clear cap space for... Myles Turner.
It's an ideal scenario for Portland, as those Bucks picks acquired in the deal look as valuable as ever. But it also makes you think about how unique the situation is for the Blazers with Lillard. To a certain extent, it reminds me of LeBron James leaving the Cleveland Cavaliers only to have them end up with Kyrie Irving and have him rejoin and win the championship.
Hopefully history repeats itself with Lillard in Portland. But teams like Cleveland and now Portland are the exception, with their blockbuster moves coming full circle and ultimately working out in their favor. The Bucks' future is currently too bleak to make them enticing enough for Antetokounmpo to rejoin.
The Bucks acquired a few promising young pieces from the Heat in the deal, but if Tyler Herro is the headline return, you'll have an issue with the ceiling of your rebuild. Antetokounmpo needs to make things work with Miami. And while this slow start in Milwaukee is predictably good news for Portland, it also reminds you how rare this rebuild is.
Cronin pulled off a Lillard trade that came full circle. He deserves a ton of credit for winning trades, bringing in pieces like Holiday, Avdija, Camara, and recently Ja Morant to accelerate this rebuilding timeline enough to fit Lillard's return. It's incredibly difficult to straddle two timelines successfully, but we're seeing them mesh beautifully to start the season in Portland, giving Lillard one of the best rosters he's ever had in the place he's wanted to be all along.
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