Poor start could force Bucks to ponder breaking up decade-long partnership

For a franchise that prides itself on its consistency and loyalty, the Milwaukee Bucks have suddenly found themselves staring at an uncomfortable reality: their 5-9 start to the season isn’t just a blip. It’s starting to read like a warning sign of things to come if something doesn't change soon.

Even their wins, encouraging as they are, have not inspired confidence. For instance, it took Alperen Sengun completely fumbling a wide-open layup under the rim for this Bucks squad to just barely squeak past the surging Houston Rockets.

Against the Detroit Pistons, it took an extra overtime period and a 59-point explosion from Giannis for Milwaukee to muster the strength to best Cade Cunningham and company.

Sitting at 12th in the East, the Bucks’ pairing of Giannis Antetokounmpo and Damian Lillard with a revamped supporting cast isn’t delivering the instant dividends fans expected. And while there are many reasons for Milwaukee’s underwhelming start, the elephant in the room for a while now has been their third star, Khris Middleton.

After years of dominance, the Milwaukee Bucks now look like a finished product that has no choice but to move forward with what they have. They have hardly any assets to move, and their aging role players command zero capital out of the trade market.

The youth movement as of late has been encouraging, but the reality as it currently stands is that this might be it for the 2021 NBA champions — unless they shake it up further by trading one of their stars.

Khris Middleton has been a pillar of the Bucks’ success for the past decade, but mounting injuries and a steep price tag might eventually force the team to ask a hard question: Can they afford to keep waiting on the trio to stay healthy — or is it time to explore trading him to maximize what’s left of the Antetokounmpo-Lillard era?

Time is not on Milwaukee's side in a loaded East playoff race

Middleton’s importance to the Bucks’ championship run in 2021 cannot be overstated. His clutch shot-making, midrange excellence, and two-way versatility were vital to Milwaukee’s title-winning formula. Yet, injuries have transformed the once-reliable forward into a question mark.

After multiple surgeries over the past two seasons, Middleton entered 2024-25 with optimism, especially after what he showed against the Indiana Pacers in the playoffs just a year before. But reality has been harsh: reports don't paint a very encouraging picture of his recovery, and the Bucks organization just hasn't been able to promise a concrete timeline for the Bucks star's recovery.

For a player earning $31.6 million this season and signed on through the 2025-26 season, one would hope for more concrete promises of a return to action.

The Milwaukee Bucks’ offseason gamble to pair Antetokounmpo with Lillard was a clear message: the window to win is now. Lillard, at 34 years old, isn’t here to play the long game. Antetokounmpo’s recent contract extension adds some stability, but his comments about needing the team to stay competitive for him to stay in town still loom large.

When Khris Middleton's return may not even ignite the spark that the Bucks need to get out of this rut, Milwaukee simply doesn’t have the luxury of patience. The Eastern Conference is loaded with title contenders like the Boston Celtics, while younger teams like the Cleveland Cavaliers are quickly rising. The Bucks can’t afford to keep waiting for Middleton to rediscover his form when every game feels like a missed opportunity to solidify their standing in the playoff race.

Trading Middleton would be a painful decision—breaking up a decade-long partnership that defined Milwaukee’s modern era. Still, the Bucks front office might eventually view it as the only way to inject new life into a team that looks stuck in neutral.

It would hurt, but there may be a real case for a trade involving Middleton

Per reports, general manager Jon Horst has been consistently working the phones and dangling names like MarJon Beauchamp, Bobby Portis and Brook Lopez for a while now. NBA insider Jake Fischer has reported that the Bucks went as far as offering a future first-round pick — their last remaining first-round draft asset for years to come — to sweeten a potential deal in the hopes of landing a perimeter defender.

Yet, no trade has materialized since this was reported.

Middleton’s proven track record could make him an appealing asset for teams looking to retool. The Bucks, in return, could target a younger, healthier player who can contribute immediately. A defensive-minded wing or athletic big man could address Milwaukee’s glaring lack of energy and versatility, while another scoring option would take pressure off Antetokounmpo and Lillard.

Names that have constantly been floated around in rumors since the offseason are Brandon Ingram and Jerami Grant - two names that aren't of the same caliber as Middleton but who are healthy, consistently playing for their teams and would seamlessly fit in the Bucks lineup. Alternatively, the Bucks could look for a package of multiple role players to bolster their depth, an area that has been sorely lacking this season.

Look, the reality is that there aren't many players out there who can replace what Middleton brings to the floor. But they'll at least be on the floor while Middleton's recovery continues to look weeks away from being weeks away.

For all the sentimentality surrounding Middleton’s tenure with the Bucks, the team’s responsibility is clear: they need to maximize the Antetokounmpo-Lillard era. That means making difficult decisions, even if it means parting ways with one of the most beloved players in franchise history.

As the Bucks continue to falter, the pressure to shake things up will only grow. Milwaukee’s season isn’t over, but the clock is ticking. If this situation continues, the pressure might just force the Bucks to make an unthinkable move: breaking up their decade-long partnership with Middleton to give their superstar duo the help they desperately need.

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