The Milwaukee Bucks are in a tight spot after starting the season 1-6. Expectations were through the roof after going all-in with the Damian Lillard trade. But instead of a deep playoff run, they got bounced early – again. Now, with Giannis Antetokounmpo openly voicing his frustrations, the Bucks are scrambling to make moves to keep him around and keep the dream alive.
Giannis recently hinted at the importance of winning for his future in Milwaukee, saying, “If we don’t win a championship, I might get traded. This is the world we’re living in… If you don’t do a good enough job, you’re out.” He emphasized that his loyalty is tied to the Bucks’ ability to compete at the highest level, reflecting his commitment to staying only if they’re serious title contenders. With this ultimatum hanging over them, the front office must get creative, aiming to bring in solid pieces to keep building the contender Giannis wants.
The question is, can the Bucks piece it all together – or is Giannis’ patience finally wearing thin?
A Tough Khris Middleton Trade
Raptors receive: Khris Middleton
Bucks receive: Bruce Brown, 2025 second-round pick (via Blazers), 2026 second-round pick
The Milwaukee Bucks have a tough decision to make with Khris Middleton, who had a disastrous 2023-24 season, and is showing signs of wear and tear. Middleton averaged 15.1 points, 4.7 rebounds, and 5.3 assists per game while shooting 49.3% from the field and 38.1% from beyond the arc, but was huge in the playoffs. Yet, after recent surgeries on both ankles and lingering injury issues that have limited his court time, the Bucks might be ready to consider a fresh option. This is where Bruce Brown comes into play, offering Milwaukee the defensive boost they need without the hefty price tag that Middleton’s $33.5 million salary brings for the 2024-25 season.
Brown, a defensive piece the Bucks are quite missing, averaged 9.6 points, 3.8 rebounds, and 2.7 assists in 26 minutes per game with Toronto last season. Though not the same offensive force as Middleton, Brown’s high-energy defense, along with his ability to switch across multiple positions, would fill a critical gap in Milwaukee’s roster. Adding Brown would also help the Bucks escape the NBA’s dreaded “second apron,” a restrictive salary cap tier that kicks in harsh financial and roster penalties, limiting trade options, free-agent pickups, and mid-level exception use if they exceed it.
If the Bucks pull off this trade, the cap savings from Brown’s $23 million contract versus Middleton’s $33.5 million would be substantial. This shift would free them from second-apron restrictions, allowing the Bucks the flexibility to secure veterans on more affordable deals and build a roster that balances Giannis’ scoring firepower with defensive depth. Brown’s defensive style, which emphasizes perimeter coverage and transition hustle, would also pair well with Damian Lillard, giving the Bucks more stability in the backcourt and relieving pressure on Giannis to cover both ends of the floor.
The Raptors, on the other hand, could benefit from adding a veteran scorer in Middleton. Although recent injuries, Middleton’s skill as a shooter and playmaker would support the Raptors’ younger lineup, providing leadership and playoff experience. Alongside Scottie Barnes and RJ Barrett, Middleton’s offensive versatility could ease scoring burdens, and his contract, while significant, is manageable in the short term. Toronto would receive Middleton’s All-Star experience, potentially helping their younger players grow while enhancing their immediate competitiveness in the Eastern Conference.
Brown’s knee injury is something to watch, but it’s reportedly less severe, and he’s expected to be ready for the season soon. Meanwhile, the Bucks are cautiously optimistic about Middleton’s recovery from his ankle procedures, though he’s yet to be cleared for full five-on-five play. This calculated risk on Brown’s healthier outlook could pay off for Milwaukee, as his defensive flexibility could make him a perfect addition to support Giannis and Lillard.
In the end, this trade could position both teams for success in their own ways. The Bucks gain a defensive specialist who fits their cap structure and on-court needs better, avoiding the second apron while staying competitive to make other deals. The Raptors get an experienced scorer to guide their younger players and bring playoff-tested depth. For Milwaukee, moving Middleton now could be the difference between maintaining a contender around Giannis or facing another financially tight season without room for crucial improvements.
The Bucks Go Younger And Swap Lopez For Valanciunas
Wizards receive: Brook Lopez, 2031 second-round pick
Bucks receive: Jonas Valanciunas, Kyshawn George
The Bucks could be shaking things up by swapping Brook Lopez for Jonas Valanciunas and rookie Kyshawn George, a move that brings even more cap flexibility and younger energy to their roster. Lopez, still a defensive standout at 36, has started the season strong with averages of 10.9 points, 5.3 rebounds, and 2.4 blocks per game, though his shooting has dipped to 38%. With an expiring $23 million salary for 2024-25, his contract takes up a big chunk of the Bucks’ payroll, making it hard to stay flexible under the cap, even though they’d be below the second apron after moving Middleton. Offloading that salary could give the Bucks extra room for midseason moves, while keeping them in a solid financial position.
Valanciunas, who recently signed a three-year, $30 million deal with the Wizards, is known for his steady scoring and rebounding. This season, he’s averaging 12.8 points, 8.2 rebounds, and 3.3 assists, showing he’s still a reliable option in the paint. His $10 million annual salary would provide the Bucks with valuable cap relief, letting them avoid restrictions on future trades and signings. With this flexibility, the Bucks could bring in additional talent to support Giannis Antetokounmpo and Damian Lillard in their title push.
For the Wizards, bringing in Lopez would add a seasoned defender and mentor for their younger roster, which includes promising players like Alex Sarr and Tristan Vuksevic. Lopez’s shot-blocking and experience would be valuable assets, especially for a rebuilding team looking to strengthen its defensive fundamentals. The 2031 second-round pick from the Bucks also adds a future asset to their growing stash, aligning with their long-term strategy.
The addition of Kyshawn George to the Bucks’ side is a bonus that could prove valuable over time. George, though limited in minutes so far, shows defensive potential and could be a versatile backup in the Bucks’ rotation. His development would add depth to the Bucks’ roster without impacting their cap situation significantly.
In the end, this trade would allow the Bucks to balance their roster for a stronger title run, keeping cap flexibility while acquiring a dependable center in Valanciunas and a young talent in George. The Wizards get Lopez’s leadership and another draft pick to build around, making this deal a win-win as both teams pursue their goals for the season and beyond.
A Big Trade For Brandon Ingram’s Star Power
Pelicans receive: Bobby Portis, Pat Connaughton, MarJon Beauchamp, 2025 second-round pick (via Blazers), 2026 second-round pick (via Raptors)
Bucks receive: Brandon Ingram
With previous trades moving Middleton and Lopez in this scenario, the Bucks would need a third offensive star to complement the firepower of Lillard, Brown, Giannis, and Valanciunas. Brandon Ingram, a versatile scorer who can create his own shots and facilitate offense, could be that missing piece. Brandon Ingram is averaging 24.6 points, 6.3 rebounds, and 4.5 assists over eight games this season, shooting 50.0% from the field and 37.7% from three. Adding Ingram would give the Bucks a powerful offensive core, capable of handling the scoring load in both the regular season and the playoffs.
Ingram’s situation with the Pelicans has been somewhat tense recently, with questions over his role and his future with the team. Currently in the last year of a $36 million contract, Ingram is reportedly seeking an extension with a significant pay raise, something the team appears hesitant to offer. The Pelicans are also investing heavily in their Zion-Murray-McCollum core and have upcoming players like Trey Murphy or Herb Jones, making a large commitment to Ingram complicated.
For the Bucks, bringing in Ingram would bring a dynamic scoring option who could relieve pressure on Giannis and Lillard, giving them more balanced offensive threats. With Ingram in the lineup, the Bucks would have multiple playmakers and scorers who could open up the floor, making them a nightmare for defenses to cover. His ability to score in isolation, shoot from the outside, and create opportunities for others would complement the existing core, giving Milwaukee the offensive depth they need for a deep playoff push.
In exchange, the Pelicans would receive a package of solid players and future assets. Bobby Portis would provide interior toughness and scoring, having averaged 14.1 points and 9.6 rebounds last season, and could slide into a bigger role in the Pels interior rotation. Pat Connaughton, could give the Pelicans valuable bench depth and veteran leadership, while MarJon Beauchamp offers a young, athletic wing with defensive upside.
The trade would also allow the Pelicans to move on from Ingram’s expiring contract without risking the loss of an asset for nothing, while also avoiding a potentially high-value extension. The Bucks, on the other hand, could view Ingram’s expiring deal as an opportunity to evaluate his fit alongside Giannis and Lillard, with the flexibility to negotiate a future deal if the partnership proves successful. If Ingram excels with the Bucks, they could consider him part of their long-term core; if not, they maintain the option to pursue other players next offseason.
Overall, this trade would address Milwaukee’s need for a third offensive star and keep them competitive in the title race, while the Pelicans receive a valuable mix of players and picks to bolster their contending try. For the Bucks, bringing in Ingram could be the final move that solidifies a championship-caliber roster, giving them a chance to make the most of Giannis and Lillard’s prime years.
A Full Scale Retool For The Struggling Bucks
With a lineup featuring Damian Lillard, Bruce Brown, Brandon Ingram, Giannis Antetokounmpo, and Jonas Valanciunas, the Bucks would be a true force to reckon with. This core has everything: Lillard’s playmaking and clutch shooting, Brown’s tough defense, Ingram’s smooth scoring touch, Giannis’s all-around dominance, and Valanciunas holding down the paint. Together, these five players would turn the Bucks into a powerhouse on both ends of the court and set them up for a serious shot at the championship.
The best part? After these moves, the Bucks would stay below the second apron. This is huge because it opens up room in the cap to sign solid bench players for added depth—a luxury they wouldn’t have if they were stuck over that threshold. With this flexibility, the Bucks can stack their bench with impactful role players, keeping the team strong and balanced without worrying about restrictive cap penalties.
For their second unit, the Bucks could assemble a solid supporting cast. Delon Wright would still come in as a steady hand, offering defense and smart decision-making. Gary Trent Jr. would keep bringing some instant offense and three-point shooting. Taurean Prince would also stay on the team with his size and defensive toughness, plus he’s capable of knocking down shots from deep.
And there’s room for more. Re-signing Thanasis Antetokounmpo would keep some energy and hustle in the lineup—plus, he knows the system and the team’s vibe. Adding Davis Bertans would be another smart move for his three-point shooting, which could help stretch the floor and give the Bucks some extra firepower off the bench.
With this core lineup and a well-rounded bench, the Bucks wouldn’t just be loaded with talent; they’d have the depth to stay competitive all season long and handle the grind of the playoffs. This mix of big-time stars and dependable role players would make them one of the most complete teams in the league and a top contender for the title.
