From Title Threat to Ticking Clock: Bucks Staring at Harsh Offseason Reality

The Milwaukee Bucks are staring at the harshest truth in sports: championship windows don’t stay open forever.

Coming off a 48-win season and their third straight early-round playoff exit, the Bucks are no longer a title contender in any real sense. Not with an aging core, limited draft capital, and uncertainty surrounding key free agents. Injuries played to Giannis Antetokounmpo and Damian Lillard a part in the slide, but the larger concern is what lies ahead, not behind.

Milwaukee’s streak of nine straight playoff appearances is impressive. It’s also in danger of becoming meaningless if the Bucks can’t find a way to rebuild around Antetokounmpo, who remains under contract through at least the 2026–27 season. The issue? Lillard will turn 35 in July and is owed $113 million over the next two seasons. Khris Middleton is gone, Kyle Kuzma is the new third option, and the supporting cast is filled with question marks.

Brook Lopez, Bobby Portis, Taurean Prince, Kevin Porter Jr., Gary Trent Jr., and Pat Connaughton could all become free agents. Portis and Porter have player options; Connaughton’s $9.4 million decision is due by June 24.

There is at least one positive: Milwaukee finally has some financial breathing room. Swapping Middleton for Kuzma shed long-term salary and pushed the Bucks below the second apron, opening up the full $14.1 million non-taxpayer midlevel exception. Whether they use it wisely remains to be seen.

But re-signing Lopez, who turns 37 in April, would bring them right back into tax territory. The franchise has already paid $220 million in luxury tax penalties since 2019–20 and is staring at a sixth straight year over the tax line if it brings back the current core. For a small-market team, that’s a big commitment to a roster with diminishing returns.

“The window closes when your core gets old and there’s no young group behind it,” one Eastern Conference general manager told ESPN during the regular season. That quote feels tailor-made for Milwaukee.

Lopez remains productive — one of only five players this season with 100 3-pointers and 100 blocks — but durability and decline are real concerns. Portis remains a fan favorite, but his $13.4 million option could become valuable trade filler or flexibility. And Trent, who averaged 18.3 points on 54.5% from three in the playoffs, likely priced himself out of a minimum contract and into a chunk of the MLE.

General manager Jon Horst has never been shy. Since taking over in 2017, he’s made 25 trades, sending out seven first-round picks, 18 second-rounders and three pick swaps in the process. The result? Just two players remain from the 2021 title team: Antetokounmpo and Lopez.

That aggression made Milwaukee a consistent regular-season winner. Since 2016–17, only Boston has won more games. But the bills are due, and the Bucks now own just one tradeable first-round pick (either 2031 or 2032), and limited salary flexibility beyond their three-man core of Antetokounmpo, Lillard and Kuzma, who will combine to earn $130 million next season.

Kuzma shot just 30.7% from three this season and ranked 188th out of 197 qualified players in that category. His new role offers hope, but not certainty.

If the Bucks don’t bring back Lopez or Portis, a frontcourt hole opens wide. The team needs depth, shooting, and perhaps most critically, a legitimate plan for the future. Milwaukee was +55.2 in net rating when Antetokounmpo shared the floor with Trent, Porter Jr., and AJ Green — a sliver of hope. Green, who hit 42.7% of his threes this season, is eligible for an extension worth up to four years and $89 million. He becomes an unrestricted free agent in 2026 if no deal is reached.

As for Lillard, he was once viewed as a likely extension candidate. That conversation has cooled significantly following his Achilles injury. It’s hard to imagine Milwaukee doubling down with another $65.5 million in guaranteed money.

Milwaukee holds the No. 47 pick in June’s draft but has just two future picks it can trade (either 2031 or 2032) and only $110,000 in available cash to buy a pick. Any major move likely waits until after July 6, when new league year rules allow greater flexibility.

Bottom line? This offseason will test everything. That includes the front office’s creativity, the ownership’s spending appetite, and how far Antetokounmpo’s loyalty can stretch.

Milwaukee’s window hasn’t slammed shut yet. But the hinges are creaking.