Bucks ‘All-In’ on Winning Title Before Window Closes, Say Insiders

The Milwaukee Bucks have gone "all-in" on competing for a title after a series of bold moves this summer, two insiders claim.

Per Tim Bontemps and Kevin Pelton of ESPN, Milwaukee is now committed to "winning a championship before the window closes" around nine-time All-NBA superstar forward Giannis Antetokounmpo.

The Bucks opted to stretch and waive the $112.6 million contract of nine-time All-Star point guard Damian Lillard, rather than wait for the 6-foot-2 Weber State product to recover from his brutal Achilles tendon rupture and perhaps recoup some of his value on the court. Realistically, the 35-year-old could be back — at the absolute earliest — at the very end of the 2025-26 regular season. On his new club, the Portland Trail Blazers, there's absolutely no rush, however, and he may just hold off to return until 2026-27.

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Milwaukee used the new cap space it had created by lessening its annual obligation to Lillard to sign Myles Turner, a 3-and-D center formerly of the Indiana Pacers, to a four-year, $108.9 million deal. The Bucks also brought in Orlando Magic guards Cole Anthony and Gary Harris to help improve their backcourt depth sans Lillard. Milwaukee retained several of its own players in free agency, including sixth man big Bobby Portis, center Jericho Sims, forward Taurean Prince, and guards Kevin Porter Jr., Gary Trent Jr. and Ryan Rollins.

"Arguably no team in the league is living more in the present than the Bucks, who under general manager Jon Horst have repeatedly swung for the fences to keep superstar Giannis Antetokounmpo happy. Five years ago, the move was to acquire Jrue Holiday," write Bontemps and Pelton.

"Two years ago, it was to use Holiday as part of the package to acquire Damian Lillard. And, this summer, it was waiving-and-stretching the two years and over $110 million remaining on Lillard's contract to allow Milwaukee to sign center Myles Turner in the team's latest attempt to both keep up with the rest of the East contenders and to keep Antetokounmpo in Milwaukee moving forward," the ESPN pundits observe.

Here's the caveat with their claim: the Bucks aren't good enough to win anything with this current roster. Milwaukee fell in five quick games to Indiana during the first round of the playoffs last year, and the Bucks haven't even been out of the first round in any of the last three seasons.

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Turner is now the club's second-best player, and although he represents a significant upgrade over an aging Brook Lopez (eight years his senior), the Bucks have a severe creation deficit in the backcourt. Yes, an Antetokounmpo/Turner/Portis/Sims front line is quite intimidating, especially if augmented by a revitalized Kyle Kuzma playing his natural position (the four) and perhaps Taurean Prince playing up a bit. But it's not enough.

In the backcourt, bringing back Harris and Porter on team-friendly deals was a good step, as was signing Anthony. Rollins has theoretical room to grow. But none of these players have the chops of a Holiday or a Lillard. It's hard to see the Bucks actually keeping pace with the Eastern Conference's likely top tier next season — teams like the Cleveland Cavaliers and New York Knicks boast multiple All-NBA talents and significantly better guard play.

Even if Antetokounmpo is the conference's best player, he's a bit on an island with this limited Bucks roster.

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