The Milwaukee Bucks are only four years removed from winning a title with the same prime-age franchise player they have today. It's a reality that's functioned as both motivation and an unenviable source of championship-or-bust expectations.
As the 2025 NBA trade deadline nears and the Bucks face the reality of how long four years truly is, however, they must come to terms with the fact that their championship core must be broken up.
The 2024-25 roster plays home to five players who helped Milwaukee win the championship in 2020-21. That list features crucial figures Giannis Antetokounmpo, Pat Connaughton, Brook Lopez, Khris Middleton, and Bobby Portis Jr.
In a perfect world, that group can be kept together moving forward, with seven-time All-NBA honoree Damian Lillard elevating the team to championship status once more.
Unfortunately, the Bucks are 12.0 games back of the Cleveland Cavaliers for the No. 1 seed in the Eastern Conference and 5.0 behind the New York Knicks for No. 3. More alarmingly, they're fighting for home-court advantage in the first round of the playoffs with the Indiana Pacers.
Compounded by the fact that Lillard and the five championship-winning players are making a combined $174,244,174 in 2024-25, the Bucks have no choice but break up the core if they hope to improve at the trade deadline.
Bucks must break up the championship core to make a meaningful trade
The often-overlooked truth about the Bucks is that they're trending in the right direction. Since starting the 2024-25 regular season with a dreadful record of 4-9, they've gone 21-11, including a 9-4 mark over their past 13 games.
While they continue to win more often than they lose, the Bucks have failed to bridge the gap between where they are and where they hope to be—thus necessitating a trade.
Milwaukee continues to hope that Middleton will play like an All-Star again, thus operating as the player who helps the team make the leap. He missed 49 games in 2022-23 and 27 in 2023-24, however, and has already missed 24 in 2024-25.
Even when he is healthy, Middleton has understandably struggled to rediscover the form that made him an NBA champion—the primary reason the Bucks are in their current predicament.
Middleton has a $34,012,345 player option for the 2025-26 season, which one can expect him to accept based on how injuries have negatively impacted his market value. As such, trading the 33-year-old could prove remarkably difficult, especially with the trade deadline nearing.
Unfortunately, that could result in the Bucks needing to trade one or even both of Lopez and Portis to make a trade of any real significance ahead of the deadline.
It's an unfortunate truth to consider, as Lopez's interior defense, and Portis' super-sub tendencies have been invaluable to Milwaukee's success. Connaughton has struggled with injuries and efficiency, however, and Lopez's expiring contract and Portis' affordable player option at $13,445,754 could become the Bucks' most tradable assets.
It would be hard to watch players who helped Milwaukee win a championship leave for the sake of roster improvement, but it may prove necessary to salvage the Antetokounmpo and Lillard era.