Everything Damian Lillard has gone through over the last few months has led to a three-year deal with the Trail Blazers, the franchise where he spent the first 11 years of his career. Lillard's teammate until this month, Giannis Antetokounmpo, should be taking notes for his future in Milwaukee.
Lillard back with Blazers like he never left
Back in summer 2023, the Bucks pulled off a blockbuster, sending Jrue Holiday to Portland and bringing in Lillard from the Blazers. Worth $42 million and including a no-trade clause, when finalized, Lillard's new contract will ironically unite the two point guards in Portland.
For all intents and purposes, the monster move did not work out for the Bucks. Hindered by injury, they again failed to escape the first round each of the past two seasons. Giannis missed the playoffs in 2024. Lillard missed two games then and, in 2025, ruptured his left Achilles' tendon after playing one game and a quarter after returning from the blood clot.
As a result of waiving and stretching Lillard's salary, the payroll will absorb around a $20 million dead cap hit per season for five years. When all is said and done, the trade might be a total disaster.
Before Lillard became a Buck, fans and media had long exhorted him to leave the Blazers team, which was heading for a full-blown rebuild, arguing that he had paid his dues. Often with limited help around him, he led them to the playoffs every season from 2014 to 2021. On its own, Dame Time could only take the Blazers so far. The 2019 Conference Finals were as far as they advanced under Lillard's lead.
Many applauded him for finally asking out, setting the stage for the formation of the Bucks' two-headed monster. During the two years it existed, Lillard and Antetokounmpo were the league's highest-scoring duo.
Gaudy stats aside, however, the pair never quite found their groove, producing confusion at times and a sluggish pace on offense.
Now Lillard is back in the city that drafted him, where he competed for scoring titles and dedicated his prime. According to ESPN's Shams Charania, the two sides were earnestly invested in orchestrating a reunion. Whether or not Lillard plays this year, he will be 36 by the time he returns ready for a full season. The contract could be his last before retirement.
Lillard deal carries caveat ahead of next offseason for Giannis, Bucks
Antetokounmpo should be watching this unfold with a notepad in hand. Having spent 12 seasons in Milwaukee, his situation is similar to Lillard's in Portland: that of the loyal superstar urged to cement his legacy by seeking greener pastures.
There are, of course, some circumstantial differences. Giannis has already won a championship, Milwaukee's first in 50 years. He's captured two MVPs. While the Bucks have work to do to become clear title threats, they are still a playoff-caliber team.
By no stretch of the imagination are they preparing for a rebuild. The front office reiterated their commitment to winning in Antetokounmpo's prime by aggressively signing Myles Turner in free agency, the move that required waiving Lillard.
The relationship is mutual. Despite the frenzied discourse over his potential departure from the Bucks, he has never expressed a wish to leave Milwaukee. Recent playoff shortcomings aside, based on everything Giannis has said, he seems happy here. The city loves him. He is larger than life. He is as much the face of an NBA franchise as a player can be.
Ring culture, though, will always pressure a player of Giannis's level to do more, everything possible to lock up his legacy and throw out the key. As good as Lillard was in Portland, twice eclipsing 30 points per game, he never reached that perennial top-three status. Few players do. For that reason, Antetokounmpo won't have the luxury of settling into eventual retirement with a single ring. He himself has named winning as another core goal.
With Giannis eligible for an extension next summer, and a player option looming for 2027-28, he and the Milwaukee Bucks aren't far off from a career-defining fork in the road.
There's a moral to this story
Still just 30, Giannis has a lot of prime left. He also has a lot to lose by jumping ship. In his brief Bucks hiatus, Lillard sacrificed only two years of his career, in addition to the time he'll miss recovering. How will it affect Giannis if he bounces between multiple teams in his final seven or eight seasons? Joining a franchise with its own star and favorite players brings unique complications.
If things go wrong, a new fanbase won't extend the same unconditional affection as Bucks fans, in whose eyes Giannis can do no wrong.
Even success is no guarantee of a boosted legacy. Many around the league discredit Kevin Durant for his two titles with the superteam Warriors. Since leaving the Thunder, he has made stops on four different teams. He will end his career reputed to be among the greatest of all time but also as a mercenary.
Lillard's career arc represents a cautionary tale to younger stars in Antetokounmpo's position. He left Portland to try and win elsewhere, but it didn't work, and now he's two years wiser. It would be unfair to call his Bucks tenure a waste, but would he do it again? Despite interest from numerous contenders in the league, Lillard returned to a Blazers squad still years away from fighting for a title.
Lillard's foray did not produce the hoped-for championship. Even in the ripest of opportunities, a ring is anything but guaranteed. Wherever he might go, Antetokounmpo would be unlikely to enjoy the status he has as the unofficial mayor of Milwaukee.
Some questions only Giannis and perhaps time can answer, but Lillard's experience suggests that the grass isn't always greener. Bucks fans obviously hope the franchise hero stays forever. For Giannis, too, there might be more to lose by leaving than first meets the eye.