The Milwaukee Bucks were prepared to pursue a major trade for Damian Lillard during the offseason, aiming to secure a new co-star for Giannis Antetokounmpo before his prime years slip away. However, Lillard’s injury disrupted those plans, forcing the Bucks to shift from bold trade attempts to more cautious roster adjustments.
Sources revealed to ESPN that the Bucks initially viewed acquiring Lillard as a “last-ditch” effort to strengthen their championship chances. Yet, with Lillard sidelined by an Achilles tear, the team had to abandon that strategy. Coupled with their limited depth, Milwaukee settled on smaller moves to maintain competitiveness.
When you talk about winning a championship, it takes time. I don’t think they had time to do that.
—Source
Meanwhile, Giannis Antetokounmpo’s future with the Bucks remains uncertain. Reports indicate he has not decided whether to extend his tenure with the franchise, prompting Milwaukee to work diligently to prove they remain a viable contender and deserve his loyalty. Their priority now is regaining Giannis’ trust through strategic roster decisions that enhance their title prospects.
Despite Lillard’s injury, the Bucks’ prior intent to trade him highlights the frustration after two consecutive postseason disappointments, where they failed to advance in the playoffs. The front office believed acquiring a new star alongside their two-time NBA MVP was necessary to change course. Lillard’s production last season — averaging 24.9 points, 4.7 rebounds, and 7.1 assists per game — would have made him a valuable trade asset, with teams like the Miami Heat and Portland Trail Blazers as probable suitors.
Once the Achilles injury occurred, the Bucks waived Lillard and stretched his contract to clear salary cap space, which they then used to acquire veteran big man Myles Turner. Alongside Turner, Milwaukee has assembled a solid group of capable role-players, including Gary Trent Jr., Kevin Porter Jr., Taurean Prince, Kyle Kuzma, and Bobby Portis, who are expected to contribute significantly.
As the Bucks reshape their roster and identity around Giannis, the pressure mounts to prove the team is still a championship contender in the Eastern Conference. Giannis is closely evaluating their chances, knowing any doubts about the roster’s strength could lead to repercussions for the franchise.
Meanwhile, Damian Lillard has returned to Portland, where he started his career, offering a chance to close his journey with the Trail Blazers. Though his time with Milwaukee did not meet expectations, it offered him valuable insights, reaffirming that his best opportunities lie where he is truly supported. As the Bucks move forward with their revamped squad, Lillard focuses on playing for a team that maintained faith in him throughout.
The Bucks’ Strategic Moves to Keep Giannis Committed
After missing out on a healthy Lillard trade, the Bucks quickly turned to reconfiguring their roster in hopes of appealing to Giannis Antetokounmpo’s championship aspirations. Adding Myles Turner strengthened their frontcourt presence, complementing a group of role-players ready to impact games consistently. Gary Trent Jr., Kevin Porter Jr., Taurean Prince, Kyle Kuzma, and Bobby Portis all figure prominently in Milwaukee’s plans to sustain competitiveness.
These moves reflect the franchise’s urgency and willingness to evolve, recognizing that Giannis’ future depends on the team’s ability to contend for titles immediately. The Bucks aim to assemble a well-rounded roster that maximizes their star’s dominance while addressing previous playoff shortcomings.
Damian Lillard’s Departure Marks a New Chapter for Both Sides
Lillard’s return to Portland represents a full-circle moment for the franchise legend. His brief stint in Milwaukee, though not fruitful, provided important lessons about fit and opportunity. Now back with the Trail Blazers, he has the chance to lead the team that originally drafted him and where his legacy was forged.
For the Bucks, moving on from Lillard is part of redefining their identity amid uncertainty around Giannis’ commitment. The franchise’s ability to navigate this delicate phase will be critical in maintaining their status as Eastern Conference contenders and keeping their two-time MVP at the helm.