The Milwaukee Bucks just detonated their roster in one of the wildest offseason moves of the year. Less than a year after trading for Damian Lillard, the front office waived him, opting to stretch his contract over five years. The decision wasn’t just a financial maneuver; it was more of a statement. And now, with their co-star gone, all eyes shift to Giannis Antetokounmpo and the increasingly uncertain path ahead.
Giannis has been Milwaukee’s heartbeat since arriving in 2013. He’s under contract through 2026-27 but holds a player option for the following season. But with the Bucks floundering and back-to-back first-round exits stinging their resume, his future feels shakier than ever. Even Lillard’s arrival couldn’t save Milwaukee from early playoff heartbreak. And now, the franchise hasn’t sniffed the Conference Finals since lifting the trophy in 2021.
The move to cut Lillard followed a brutal injury blow. Just two months ago, Dame ruptured his left Achilles in Game 4 against Indiana. An injury that is expected to sideline him for most, if not all, of the 2025-26 season. And the Bucks capitalized on the unfortunate situation, clearing cap space to pursue Myles Turner. He has been the Pacers’ defensive anchor and a key figure in their NBA Finals run. The plan is obvious. Pair Turner with Giannis and hope it’s enough to keep their superstar tethered to Milwaukee.
But is it too late? On a recent episode of Good Word with Goodwill, Vincent Goodwill raised an unsettling concern. Vincent said, “With the way he (Giannis Antetokounmpo) plays, the violent nature of how he plays, I don’t know how much longer he can continue to play this way in a healthy way, coming up on age 31. And honestly, he’s not wrong. Giannis’ relentless, physical style has always carried risk, and as he crosses into that injury-prone 30-plus window, those risks compound.
He also added, “So he almost has to he should be looking hot take here. He should be looking at Damian Lillard and saying You know what, Damian Lillard waited two years too long before he made his trade request. Don’t let that be me.”
Apr 10, 2025; Milwaukee, Wisconsin, USA; Milwaukee Bucks forward Giannis Antetokounmpo (34) warms up before game against the New Orleans Pelicans at Fiserv Forum. Mandatory Credit: Benny Sieu-Imagn Images
The league rarely has patience for aging, injured stars with heavy contracts, and Lillard’s exit was a cold reminder. Milwaukee Bucks cutting ties wasn’t personal because it was business. Vincent’s warning to Giannis feels more like a survival strategy than a hot take. But that discussion didn’t end there. While speculating about Dame’s next move, a potential landing spot surfaced. One that could redefine the late chapter of Lillard’s career. And if that materializes, it might just send ripples through both conferences.
The next most suitable stop for Damian Lillard
The next chapter in Damian Lillard’s career suddenly feels wide open. For the first time ever, the nine-time All-Star finds himself a free agent, and while plenty of teams would love to have him, there’s a catch. Lillard, now in his mid-30s, is recovering from a ruptured Achilles, an injury notoriously difficult to bounce back from at this stage in a player’s career.
Even before the setback, Lillard was still putting up serious numbers. Last season with Milwaukee, alongside Giannis Antetokounmpo, he averaged 24.9 points, 4.7 rebounds, and 7.1 assists while shooting 44.8% from the floor and 37.6% from deep. On paper, he remains one of the league’s elite guards. But whether he’ll return at 100% is anyone’s guess, and whichever franchise bets on him now will likely have to sacrifice a season waiting for him to heal.
That’s why Amin Elhassan made a compelling case on the same podcast for an unexpected reunion. A return to the Portland Trail Blazers. Yes, the same team that drafted Lillard, raised his profile, and turned him into a global name. And, perhaps just as importantly, the city where his family still calls home.
Amin explained, “Who’s a better professional and a better leader than Damian Lillard? You come in, you rehab under us, we get you right. In the meantime, you’re not going to be isolated from our team. We want you around our rookies. We want you talking to guys, letting them know things on the Why Portland might actually make sense again court, things off the court, how to approach, diet, exercise, social life, all those things.” And honestly, it makes sense. Even if Lillard isn’t torching defenses for 25 a night, his leadership, experience, and influence could shape Portland’s young core.
Meanwhile, the Milwaukee Bucks are now banking everything on Giannis Antetokounmpo, trying to retool their roster without his former co-star. The franchise’s future hangs entirely on Giannis’ loyalty and whether the moves they’re making now can convince him to stick around long-term. Because if this gamble doesn’t land, Giannis Antetokounmpo might soon be weighing his own next chapter too.
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