Damian Lillard’s return to Portland is already looking like the kind of rare homecoming that almost never happens in the NBA. For Giannis Antetokounmpo, though, it’s also a reminder that not every star who leaves home gets the same ending.
Antetokounmpo didn’t want to walk away from the family, the home, and the community he built in Milwaukee. At the same time, he understood the hard truth that if he wanted a real shot at contending, he might have to do it somewhere else. That same kind of tug-of-war is what Lillard dealt with when he asked out of Portland in 2023.
Now Giannis is the one seeing that the grass is not always greener.
The new-look Miami Heat are only 2-5, and while there’s still a long way to go, this doesn’t look like a team built to contend unless something dramatic changes before February’s trade deadline. That’s the kind of start that makes you ask whether leaving Milwaukee was worth it.
Lillard has already answered that question for himself. He came back to Portland just two seasons later, and he was clear that the move was not just about being close to family. It was, in his words, a “basketball decision” to win games.
So far, that decision looks pretty sharp. The Blazers are 5-1, and Lillard appears to be the perfect answer to the floor-spacing problems that showed up last season.
Still, Portland wasn’t starting from scratch when Lillard returned. The Blazers were already a playoff team last year, and a big reason for that was the haul they got when they moved him out in the first place. That group includes an All-Star in Deni Avdija, an elite 3-and-D piece in Toumani Camara, an ascending rim protector in Donovan Clingan, and potential Sixth Man of the Year Jrue Holiday.
That’s where the comparison to Antetokounmpo starts to break down.
If Giannis ever wanted back in Milwaukee down the road, the Bucks wouldn’t be in anything close to the same position. They owe future draft picks to the Blazers and other teams, and they still owe Lillard $22.6 million annually after waiving and stretching the remaining $113 million to create cap space for Myles Turner.
That’s a very different setup from Portland’s. The Blazers’ picks from the Bucks look more valuable than ever, and the deal has given them a path that actually makes Lillard’s return possible. It’s the kind of rare situation that makes you think of LeBron James leaving Cleveland, only for the Cavaliers to wind up with Kyrie Irving and later bring LeBron back to win a championship.
That’s the dream for Portland now, too. But teams like Cleveland and Portland are the exception, not the rule.
Most blockbuster trades don’t circle back like this. Most don’t end with the original star coming home to a better situation than the one he left.
The Bucks’ future is simply too thin to make that kind of reunion feel realistic for Antetokounmpo.
Milwaukee did get some promising young pieces back from Miami in the deal, but if Tyler Herro is the centerpiece of the return, that tells you plenty about the ceiling of the rebuild. Giannis needs Miami to make this work.
And while Milwaukee’s slow start is obviously good news for Portland, it also underscores just how unusual this whole setup is. Cronin deserves a ton of credit for making the Lillard trade work in a way that brought back Holiday, Avdija, Camara, and recently Ja Morant, all while speeding up the rebuild enough to line up with Lillard’s return.
It’s hard to balance two timelines at once. Right now, Portland is doing it beautifully, and Lillard is back in a place he’s wanted to be all along, with one of the best rosters he’s ever had.
In Other News...
Blazers Keep Getting Better News From The Damian Lillard Trade
The Damian Lillard trade keeps looking better for Portland, not just because of what the Blazers received in the deal, but because of how the rest of the transaction has played out since. Milwaukee has been trying to navigate an early-season slump after parting with Giannis Antetokounmpo, and the ripple effects of the Lillard move have only added to the sense that Portland came out ahead in a major way.
For the Blazers, the return was always about more than one player, and the draft capital attached to the deal has given the franchise more flexibility as it tries to build forward. Milwaukees decision to waive Lillard to create cap room also underscored how much long-term financial maneuvering came with the trade, leaving Portland with a package that keeps gaining value as the Bucks continue to sort through the fallout. [Read more 🡒]
Blazers Fans May Not Like How Close This Suns Rematch Looks
The Trail Blazers are heading into their rematch with the Suns in a familiar spot for an early-season contender: dealing with injury absences while still trying to keep the momentum rolling. Portland is expected to be without key players Ja Morant and Shaedon Sharpe, which makes the matchup a little trickier on paper, even as the Blazers have opened the season strong and remain the models pick to win.
For fans, the interesting part is how tight this one looks against the betting market. The simulation projections point toward Portland, but they also suggest a game that could stay close enough to test whether the Blazers can keep turning solid starts into actual results. With the Suns back on the schedule, the margin for error feels slim, and the numbers are leaving just enough room for a tense finish. [Read more 🡒]
Sidy Cissoko Is Quietly Solving A Blazers Problem Joe Cronin Bet On
Joe Cronins decision to stand pat on the wing after the offseason has looked a little less risky with each passing game. The Trail Blazers did not go out and chase a replacement for the players they lost, trusting the roster already in place, and Sidy Cissoko has started to look like the kind of internal answer that can make that bet work. The 22-year-old has carved out a real role off the bench, bringing a steadier offensive touch and the kind of defensive versatility Portland can use in a rotation that still has some sorting out to do.
Through the first six games, Cissoko has given the Blazers something beyond a temporary hot stretch. His shooting has improved, his activity on the other end has fit what the team needs, and the minutes he is getting do not feel accidental. Portland is intentionally making room for him, which says plenty about how the staff views his place in the rotation and how much confidence there is that this two-way impact can hold up. [Read more 🡒]