The Milwaukee Bucks entered this offseason with championship aspirations still firmly in mind, but also with a clear understanding that their margin for error has shrunk dramatically in a top-heavy Eastern Conference. The Bucks’ core of Giannis Antetokounmpo, Damian Lillard, and Khris Middleton still gives them one of the most potent trios in basketball, yet last season showed glaring holes in depth, defensive versatility, and perimeter shooting that proved costly. After bowing out earlier than expected in the playoffs, Milwaukee had a golden opportunity in free agency to address these weaknesses decisively. Instead, their moves were relatively conservative, and while they maintained roster continuity, they missed the chance to make a bold acquisition that could have elevated them from mere contenders to the unquestioned favorite. The bold move they should have made was aggressively pursuing a two-way wing with size, shooting, and defensive chops—someone in the mold of a Jerami Grant, OG Anunoby, or even a high-upside gamble like a Derrick Jones Jr. This type of player could have been the missing piece that balanced the roster, allowing the Bucks to match up better against elite wings like Jayson Tatum, Jaylen Brown, Jimmy Butler, and even the emerging Paolo Banchero. It’s not just about adding talent for talent’s sake; it’s about plugging the specific gaps that caused Milwaukee trouble last year. With Brook Lopez aging and Middleton still working his way back to consistent health, the Bucks are more vulnerable on defense than in years past. They have a stellar rim protector in Lopez and one of the league’s best transition defenders in Giannis, but they lack a reliable perimeter stopper who can both contest shots and switch across multiple positions without sacrificing offensive spacing. This is where a bold free-agent swing could have made the difference. Imagine if Milwaukee had been willing to part with mid-level salary fillers and perhaps a future draft asset to execute a sign-and-trade for a wing like Grant, whose length and switchability fit perfectly next to Giannis. Not only would that have given them an extra scoring option capable of creating his own shot, but it would also have taken immense defensive pressure off Antetokounmpo, who too often has to cover for multiple teammates in crunch time. The Bucks’ playoff struggles in recent years have followed a pattern. They lean heavily on Giannis to create offense in half-court settings, and when defenses load up on him, the secondary and tertiary creators must produce. While Lillard’s arrival last season added the dynamic scoring threat they had long lacked, the drop-off after the top three scorers is still significant. Relying on role players like Pat Connaughton, Malik Beasley, or Jae Crowder for big playoff moments has yielded mixed results. These players have their strengths, but in high-stakes playoff series, it’s often the versatile two-way wings who swing games and series. This is why a bolder move in free agency was warranted. The Bucks needed someone who could hit corner threes, attack a closeout, and defend the other team’s best scorer without being a liability on the other end. Players like Anunoby don’t become available often, but even pushing hard for someone in the next tier down—such as Kyle Anderson or even a Kelly Oubre Jr. on the right deal—could have been the kind of strategic gamble that separates contenders from champions. Free agency is not just about reacting to market value; it’s about anticipating playoff matchups months in advance. When looking ahead to next season’s Eastern Conference playoff picture, Milwaukee will likely have to go through at least two of Boston, Miami, New York, Philadelphia, or Cleveland to reach the Finals. Each of those teams has multiple scoring wings and versatile defenders who can switch onto guards and bigs alike. The Bucks, as currently constructed, still face the risk of getting picked apart in mismatches, particularly if Middleton is hobbled or if Lopez gets drawn out to the perimeter. A bolder move could have mitigated those risks. The tricky part for Milwaukee is their cap situation. They’re a tax-paying team with little financial flexibility, but that doesn’t mean bold moves are impossible. Sign-and-trade frameworks, minimum deals with upside, or even using the taxpayer mid-level exception creatively could have netted them an impactful player. Other contenders have shown that resourcefulness matters just as much as cap space. The Phoenix Suns last year managed to land key depth pieces despite financial constraints, and the Denver Nuggets were able to shore up their rotation with shrewd moves. Milwaukee, instead, chose continuity, perhaps believing that better health and more time for their core to mesh would solve last year’s problems. While there’s merit in that approach—chemistry does matter—the NBA’s arms race is unforgiving. Standing still while your rivals reload can leave you behind. The Boston Celtics, for instance, doubled down on their strengths by extending Jrue Holiday and trading for Kristaps Porziņģis. The New York Knicks made a statement move by trading for Mikal Bridges, giving them perhaps the best defensive wing rotation in the league. Even the Miami Heat, known for patient roster building, are always in the mix for a big splash when it fits their culture. The Bucks, in contrast, seemed to play it safe, re-signing familiar faces and banking on internal improvement. Safe is not necessarily bad, but when your championship window is now, boldness is often rewarded. Giannis has made it clear in past comments that he wants to contend every season and will assess his future based on the franchise’s commitment to winning. That urgency should have fueled a more aggressive pursuit of roster balance. The Bucks have the star power to win it all, but the supporting cast must be optimized for playoff battles. A bold free agency move this summer could have set them apart from the pack, giving them not just a better regular season but a far more dangerous playoff profile. Without that move, they are relying heavily on health, luck, and incremental improvement—variables that can be unpredictable in the postseason. The Bucks may still win the title next year because Giannis and Lillard are capable of transcendent runs, but their path will be harder than it needed to be. They had the chance to add the kind of two-way wing every contender covets, and passing on that opportunity might be the difference between another early exit and hoisting the Larry O’Brien Trophy. The NBA rewards calculated aggression, and while Milwaukee’s conservative offseason might keep them in the hunt, the absence of a bold, targeted addition could haunt them when the games matter most. If the Bucks fall short again next spring, they may look back at this summer and wonder what could have been had they pulled the trigger on that one move to push them over the top.
The Milwaukee Bucks should have made this bold move in free agency to improve the roster for a deep playoff run next season
