The last two months have been horrific for Damian Lillard. Just when he proved science wrong and recovered from a deep vein thrombosis in just over a month, game 4 against the Pacers dealt him a worse injury blow. Seems like the Bucks’ Ls go much past their 129-103 loss to Indy on home court. There’s no proper diagnosis, but it does seem like Dame Time has clocked out for the season.

Lillard went down with 6:08 remaining in the first quarter while trying to gather an offensive rebound. Sat in and around the logo, Dame planted his left foot to go after the ball and immediately crumpled to the floor, clutching at his left heel. They even had to draw a foul to stop play. Kyle Kuzma did pick him up, but it was at that moment he knew the severity. The reporters on Brian Windhorst & the Hoop Collective broke it down properly.

“Torn Achilles is, you know, for a guy in his 30s, it’s a career-threatening injury, but okay. It’s going to decimate the 2025-26 season for Dame Lillard, which is going to decimate the Bucks’ outlook for 25-26,” said Windy. The fact that his blood clot was discovered early was “lucky,” he said. But for Tim Bontemps, Damian Lillard’s recent injury gives him flashbacks to another successful team which was set back comprehensively by injuries.

“And I thought a lot about 2019 and being around Raptors, Warriors and seeing Kevin Durant get hurt and then seeing Klay get hurt. And that set the Warriors back for a couple of years.” This could ring alarm bells for someone like Giannis Antetokounmpo.

“But yeah, I mean, it just, it just really sucks. And, you know, we, we talked a lot about the future for Giannis and what things could look like going forward for him and for the Bucks and for the league this summer,” said Bontemps. Giannis potentially leaving the Bucks has been in the headlines for a while now. Their dependency on the Greek Freak is too evident for Doc Rivers’ liking. And they don’t seem to be getting anywhere with the current state of their squad either.

Should he stay? Should he go? Unless there’s a statement from either party directly, we’ll know. But recent developments might signal two other Milwaukee stars with uncertain futures.

Giannis Antetokounmpo’s future at Bucks amidst uncertainty about Bobby Portis Jr. and Brook Lopez

Damian Lillard’s horrific injury means that his return might not be as soon as they’d expect. Added to that, GM Jon Horst has to deal with the free agencies of Bobby Portis Jr. and Brook Lopez. For Bobby, it’s a player option that would see him play for another year before unrestricted free agency. But for Lopez? The time comes now. He’s due to be a UFA by the end of this season. And if Dame is to be out for a while, the depth will take a big hit.

“You can’t worry about their draft pick situation or anything else other than if you’re gonna make that deal, you’re only gonna get one chance to do it. You gotta maximize every ounce of it you can. On one hand, it could be clarifying because they were sort of stuck in trying to figure out what to do, especially with Brook Lopez and Bobby Portis being free agents. They’re trying to figure out a way to keep them when they’re both in their 30s,” said Bontemps. But none of this matters as much as Giannis’ situation.

Giannis Antetokounmpo is the best thing to happen to Milwaukee since their title win in 1971. But he’s far too good a player to be limited to one title alone. And if the Bucks’ current situation is something to go by, his exit could be on the cards quicker than expected. His current contract runs out in 2028-29, but his mind could change, seeing the blows Milwaukee have been dealt with recently.

Saying goodbye to an in their prime star is not as easy as agreeing with the logical whiteboard that Bontemps just said. Well, and they don’t say goodbye unless Giannis says it’s time. I understand, but you know. Look, that’s why I said I think it’s a clarifying moment for everybody. Like if Giannis wants to spend his career in Milwaukee, good for him and God bless him. Like that would be great,” talked the reporters on the pod.

But all this seems a little too familiar, doesn’t it? Giannis is just going through what Kareem Abdul-Jabbar went through in 1975. When Kareem was at Milwaukee, they were flying. But citing Milwaukee’s inability to fit his cultural needs, he privately requested a trade away from Wisconsin. That did end up happening in 1975. And guess what – they didn’t make the NBA finals until 2021, with Giannis. The Greek’s move away could repeat past misfortunes under similar circumstances.

Is the writing on the wall for Damian Lillard‘s career? Possibly. This just makes Jon Horst’s job all the more difficult. As if Brook Lopez and Bobby Portis Jr.’s contract situations aren’t enough of a headache. But seeing the hellhole the Bucks are in right now, could Giannis Antetokounmpo find himself a way out?