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Following a turbulent season filled with highs and lows, the Milwaukee Bucks front office must decide whether to stay the course with their current roster or make a bold move to capitalize on their championship window. With the Eastern Conference as competitive as ever, standing still isn't a viable option. Their ideal scenario? Acquiring Jerami Grant, a dynamic two-way player who could be the missing link to propel them from contender to title favorite.
A Season of Mixed Results
With a 26-19 record, the Bucks' 2024-25 campaign has been solid but far from dominant. They stumbled out of the gate but rebounded to capture the NBA Cup. However, since that victory, the team has struggled to regain its rhythm. This quells any speculation of an Antetokounmpo mega-trade.
Rather than pursuing drastic changes, Milwaukee is expected to explore any avenue available to improve. This is despite having limited trade assets in terms of draft picks and young talent. Moving someone like Khris Middleton for significant value seems unlikely, and while Bobby Portis might attract interest, trade buzz around him has been minimal. One viable option for the Bucks is leveraging Middleton's $31.2 million contract as the foundation for a deal. If they are willing to include their unprotected 2031 first-round pick, they could realistically land another impact player.
Milwaukee appears determined to shake up the roster. According to NBA insiders, the Bucks are “as aggressive as any team in the league” in their pursuit of a meaningful trade before the deadline.
Here we will discuss the player who's part of the Milwaukee Bucks' dream scenario for the 2025 NBA trade deadline.
The Dream Scenario: Trading for Jerami Grant
If the Bucks want to make a significant move at the trade deadline, acquiring Jerami Grant from the Portland Trail Blazers should be their primary objective. Grant addresses Milwaukee’s biggest needs: defensive versatility, shot creation, and a seamless fit alongside Antetokounmpo and Damian Lillard. His length, athleticism, and ability to guard multiple positions would immediately bolster a Bucks defense that currently ranks outside the league’s top 10.
Portland, currently in rebuild mode, has little reason to retain a 33-year-old veteran on a long-term deal. Milwaukee, in win-now mode, should be prepared to offer assets to land a player of Grant’s caliber. A trade package centered around Middleton, Pat Connaughton, and future draft compensation might entice Portland. If needed, Milwaukee could explore a three-team deal to structure the trade while addressing depth concerns.
Why Grant is the Perfect Fit
Bringing in Grant would provide the Bucks with a dynamic two-way forward. His scoring, defensive prowess, and ability to guard multiple positions make him an ideal addition. Grant’s ability to create his own shot and hit three-pointers at a 38.2 percent clip enhances Milwaukee’s championship outlook. He fills their need for a secondary scorer and defensive wing presence.
As for Khris Middleton, his tenure in Milwaukee appears to be nearing its end, as the Bucks must ensure Giannis remains satisfied with the roster. Adding Grant could reinforce the Bucks' standing as a true contender. He would enable them to compete with the Boston Celtics and Cleveland Cavaliers atop the East.
The Trade Package
Acquiring Grant would force Milwaukee to part with a key rotation player, but the potential rewards outweigh the risks. The Bucks' current roster construction leaves them vulnerable to elite opponents who can exploit their defensive gaps. A core of Giannis, Lillard, Grant, and Middleton—if healthy—would be one of the most balanced lineups in the league. Should Middleton be included in a trade package, Portis or Connaughton could step into that void.
Milwaukee faces financial constraints that complicate their trade options. The team cannot take back more salary than it sends out, cannot aggregate outgoing contracts unless they dip below the second apron, and has only one future first-round pick (2031) available to trade.
Aside from Middleton, this leaves Portis ($12.6 million) as one of Milwaukee’s most valuable trade assets. The power forward and small-ball center has been a key contributor. Trading him would not be an easy decision. However, he could help the Bucks acquire a defensively impactful wing or backup big man. Both of these are critical to shoring up Milwaukee’s rotation for a deep playoff run.
Final Thoughts
The Bucks are at a defining moment in their championship pursuit. With a roster led by two superstars in Giannis and Lillard, Milwaukee cannot afford to waste another season with roster deficiencies that could be addressed at the deadline. While acquiring Jerami Grant would require tough decisions, the potential payoff is clear: a more balanced, defensively sound team ready to compete with the best in the East. The front office must act decisively, because in the modern NBA, windows for contention close faster than ever. If the Bucks want to hoist another championship banner, now is the time to go all in.
