Since they were crowned NBA champions back in 2021, the Milwaukee Bucks have won only one playoff series. Context is important when examining a years-long bumpy ride full of devastating injuries, desperate trades, and multiple coaching changes. But professional basketball is a bottom-line industry where results will always drown out nuance.
The phrase “all in” has become somewhat of a trite way to describe overleveraged organizations with championship aspirations. Most teams that seemingly have their back against the wall will always find a way to wriggle free. For example: The Bucks appeared to be all in last season … then they traded for Damian Lillard. Voila! But once they made that deal, all avenues to improve, internally and externally, were pinched down to a millimeter wide.
Almost immediately, everything that could’ve gone wrong did go wrong. First, the Portland Trail Blazers shipped Jrue Holiday to the Boston Celtics, where the former Buck helped construct a brick wall in Milwaukee’s conference. Then incoming head coach Adrian Griffin decided to tinker with an identity that, in his players’ minds, didn’t need fixing. Milwaukee’s transition and perimeter defense grew erratic and Griffin was fired after 43 games. Through it all, Khris Middleton battled multiple injuries and never quite looked like himself, and after winning 49 games on the back of a Herculean effort by Giannis Antetokounmpo, the Bucks limped into the postseason after said Herculean effort culminated in a calf strain that forced their MVP candidate to miss the entire first round. Disaster after humiliation after disaster after humiliation.
Now after having been eliminated by the Indiana Pacers in six games, their season is over. Where do the Bucks go from here, having fallen woefully short for the third straight year? How do they get back to the mountaintop?
If you’re an eternal optimist, running the league’s second-oldest roster back with minor alterations is not the end of the world. Put this nightmare season in the rearview mirror, give Doc Rivers an opportunity to implement his system in training camp, let Dame and Giannis develop better chemistry, and hope both are healthy for the playoffs. Even though so much can change before next season’s opening night, with disgruntled stars and impatient owners potentially rearranging the Eastern Conference’s projected hierarchy, this isn’t a completely futile plan.
If that feels too stale, maybe the Bucks get a little more aggressive. What about packaging Bobby Portis, Pat Connaughton, and an unprotected 2031 first-round pick for someone like Marcus Smart or De’Andre Hunter in a potential money-saving move that a tax-conscious team could appreciate? Shopping Lillard isn’t an option thanks to his troublesome contract. Middleton is still essential. But the Bucks could look into trading Brook Lopez, who just turned 36, is on a $23 million expiring contract, and remains one of the league’s premier rim protectors. Let’s say the Bucks call the Pelicans to offer Lopez and Andre Jackson for Herb Jones and Larry Nance Jr. It’s a fascinating hypothetical full of opportunities and drawbacks for both sides. There are several other deals out there to be explored, should the Bucks make youth and athleticism their priority.
Winning a title next season under any of these scenarios is definitely possible. This year, Milwaukee’s four most common five-man units were all dominant. The Bucks’ net rating when Lillard, Antetokounmpo, and Middleton shared the floor was +17.5 and they went 28-14 when those three were healthy enough to play in the same game. The team’s margin for error was a bit more narrow than any contender wishes it to be, though, with too few paths available to correct some of the defensive issues that plagued them all season. But calm seas don’t make good sailors. Milwaukee went through hell and can learn from the experience. A team with healthy versions of Giannis, Middleton, and Lillard can be resilient, explosive, and complementary when games really start to matter.
If you’re a pessimist, though, you’re looking at this situation and waiting for someone to ask a different question. It’s entirely possible the Bucks will be awesome next season. It’s just as likely they will echo the same awkwardness and disappointment we just witnessed again. In that reality, if reshaping a genuine contender around Antetokounmpo (who will turn 30 next December) isn’t feasible due to Milwaukee’s advanced age, depleted asset pool, and cap-related inflexibility, when does either side seriously consider an exit strategy?
Yes, Giannis signed a three-year, $175.9 million extension in October that will expire after the 2026-27 season. On a sentimental level, it’d be sweet if he spent his entire career in a Bucks jersey. But all that money doesn’t completely overshadow numerous on-the-record declarations Antetokounmpo’s made within the past year about how badly he wants to win again, be it in Milwaukee or somewhere else. If “Giannis is here so we’re totally fine” is the only reason people have to be excited about the Bucks’ future, the Bucks’ future can turn grim in an instant.
That doesn’t mean they’ll become irrelevant overnight. It’d be a shock for Giannis to demand a trade this summer, being that his calf and Lillard’s Achilles were the two biggest reasons Milwaukee failed to advance out of the first round for the second straight season. But this was still a championship-or-bust season that didn’t feature any sustained stretch in which the Bucks looked capable of winning at the highest level. Their personnel was deeply flawed and one-dimensional, a frustrating truth that might’ve been in the back of Giannis’s mind when he called out his teammates’ effort and desire well after Dame was acquired, during a season that was chock-full of head-scratching losses—including two, back-to-back, in early April against the Wizards and Grizzlies (Lillard missed both).
Despite employing a two-time MVP who might be coming off his most impressive season, the Bucks’ future, at the very least, warrants concern.
There’s a chance Bucks general manager Jon Horst sees the writing on the wall and takes a job with the Pistons. There’s a chance Rivers (whose record as Milwaukee’s head coach is 19-23) can’t magically sew up Milwaukee’s raggedy perimeter defense with a roster that has no wing stoppers on it.
There’s a chance Lillard (who will turn 34 in July) never makes another All-Star team and becomes an inconsistent, fence-swinging designated hitter with a cumbersome contract. There’s a chance Lopez loses a step and their trembling defensive identity craters. There’s a chance Middleton can’t stay healthy. And there’s a chance none of the minimum-contract role players they sign this summer hit (a.k.a. “The Ishbia Special”).
The Bucks are one of the oldest teams in the league, with another exorbitant tax bill on the horizon. They’ll almost definitely cross into the second apron next year, which means, if they want to make a deal, they can’t bring in more salary than they send out, aggregate contracts, include any cash, or land someone in a sign-and-trade. They also don’t have access to the taxpayer midlevel exception, and the only picks under their control are no. 23 in this year’s draft and the aforementioned first in 2031. (The only second-round pick they can trade is also in 2031.) Daggers all around.
No ownership group is excited about paying repeater tax penalties for a team that’s stopped making deep playoff runs. At what point do they believe moving on from Antetokounmpo is the healthiest long-term play? Nothing that dramatic will happen this summer, but a breakup increasingly feels more likely than another championship, knowing a blockbuster trade could kick-start Milwaukee’s next era with a ton of draft capital and blue-chip talent. As great as Antetokounmpo is, some offers could be too juicy to pass up.
Of course, there are plenty of people who think this core could’ve won the title this season. Maybe Milwaukee just needs better injury luck. But the counter here is obvious, coming from everyone who watched the Bucks consistently struggle for the past six months. Growth is critical. Stagnancy is death. But what happens for the Bucks if they’re currently stuck in their final form?
Right now, the most relevant opinion still belongs to Giannis. But even if he has real faith in the Bucks’ commitment to winning, it’s hard to see that faith surviving another season like the one he just went through. In Milwaukee, seismic change feels impossible and, at the exact same time, like it’s right around the corner.