The Milwaukee Bucks’ acquisition of Damian Lillard in 2023 was heralded as a game-changer, a move to pair a superstar point guard with Giannis Antetokounmpo and cement the team’s status as NBA championship contenders. However, nearly two years later, the trade is increasingly viewed as one of the worst in recent Bucks history.
With Lillard’s massive contract, persistent injuries, and lackluster playoff performances, the signing has not only failed to deliver but is arguably squandering the prime years of one of the NBA’s greatest talents, Giannis Antetokounmpo. As the Bucks face a critical offseason, questions loom about whether Giannis will re-sign or seek a new team to chase another championship.
The High Cost of Damian Lillard
When the Bucks traded for Damian Lillard, they committed to a staggering financial burden. Lillard’s contract includes $54 million for the 2025-26 season, with a $58 million player option for 2026-27, making him one of the highest-paid players in the league. This deal, combined with Giannis Antetokounmpo’s $112.5 million over two years (plus a $62 million option), and Kyle Kuzma’s $42.5 million over two years, severely limits Milwaukee’s salary cap flexibility.
The Bucks’ payroll, already the fourth-highest in the NBA at $193.1 million, exceeds the salary cap by $53 million, restricting their ability to sign new talent or make significant roster changes.
The financial strain is compounded by the assets Milwaukee surrendered in the trade. The Bucks gave up All-Star guard Jrue Holiday, a 2029 first-round pick, and unprotected swap rights in 2028 and 2030. Holiday, a defensive stalwart, went on to help the Boston Celtics win the 2024 NBA Championship, while the Bucks’ lack of draft picks until 2031 leaves them with little room to rebuild or acquire young talent.
This trade has painted the Bucks into a corner, with few options to improve a roster that has underperformed.
Lillard’s Injury Woes and Playoff Disappointments
Damian Lillard, a seven-time All-Star and one of the NBA’s most clutch performers during his Portland Trail Blazers tenure, was expected to form a lethal pick-and-roll partnership with Giannis. However, injuries and inconsistent play have marred his time in Milwaukee.
In the 2024-25 season, Lillard suffered a devastating torn Achilles tendon during the first-round playoff series against the Indiana Pacers, sidelining him for the remainder of the postseason and likely much of the 2025-26 season. This injury followed a blood clot issue that had already forced him to miss significant time earlier in the season.
Even when healthy, Lillard’s impact has been underwhelming. In the 2024-25 regular season, he averaged 24.9 points and 7.1 assists, solid numbers but a step down from his Portland peak. In the playoffs, the Bucks have been eliminated in the first round in both seasons since Lillard’s arrival, continuing a streak of three straight early exits.
The Lillard-Antetokounmpo duo posted a pedestrian +4.7 net rating when playing together, far below championship-caliber pairings like Jayson Tatum and Jaylen Brown (+8.1) or Shai Gilgeous-Alexander and Jalen Williams (+13.1). Lillard’s defensive limitations, a downgrade from Holiday’s elite perimeter defense, have further exposed Milwaukee’s vulnerabilities against faster, more dynamic teams like the Pacers.
The Bucks’ championship window, once wide open after their 2021 title, now appears closed. Lillard’s injuries and age—he’ll be 36 when he returns from his Achilles injury—raise doubts about his ability to return to All-Star form, leaving Milwaukee with a bloated contract and no clear path to contention.
Wasting Giannis Antetokounmpo’s Prime
At 30 years old, Giannis Antetokounmpo remains a top-three player in the NBA, averaging 30.4 points, 11.9 rebounds, and 6.5 assists in the 2024-25 regular season and an even more dominant 33.8 points and 14.5 rebounds in the playoffs.
Despite his Herculean efforts, the Bucks have been unable to advance past the first round since 2022, a frustrating trend for a two-time MVP and 2021 Finals MVP who has repeatedly emphasized his desire to win a second championship.
The Bucks’ roster, built around aging and injury-prone players like Lillard (34) and Brook Lopez (37), lacks the youth and depth needed to compete with elite teams like the Boston Celtics or Cleveland Cavaliers. General manager Jon Horst’s decision to trade Khris Middleton for Kyle Kuzma, who has underperformed with just 10 field goals in four playoff games against Indiana, further weakened the supporting cast.
Milwaukee’s draft failures—neither of their last two first-round picks, AJ Johnson nor MarJon Beauchamp, remains with the team—have left them without promising young talent to complement Giannis.
Antetokounmpo’s frustration is palpable. He has publicly stated that his loyalty to Milwaukee hinges on the team’s ability to contend for championships, a condition the Bucks are failing to meet. With Lillard sidelined and the roster locked into expensive contracts, Giannis is left to carry an uncompetitive team, wasting his prime years and diminishing his legacy as one of the game’s all-time greats.
Will Giannis Antetokounmpo Re-Sign or Leave Milwaukee?
Giannis Antetokounmpo’s contract runs through the 2026-27 season, with a $62 million player option for 2027-28. While he has expressed love for Milwaukee, where he’s spent his entire career and raised his family, his patience appears to be wearing thin. In August 2023, he told The New York Times that he wouldn’t sign an extension unless he believed the Bucks were fully committed to winning, a stance that prompted the Lillard trade. Although he signed a three-year, $186 million extension in October 2023, trade rumors have intensified following Milwaukee’s latest playoff collapse.
If the Bucks fail to make a deep playoff run in 2025-26, Antetokounmpo could request a trade, potentially as early as the 2026 offseason when he’s two years from free agency. Teams like the Brooklyn Nets, Miami Heat, Golden State Warriors, and Oklahoma City Thunder are reportedly monitoring his situation, with some prepared to offer young stars and draft picks for the chance to pair Giannis with players like Stephen Curry or Shai Gilgeous-Alexander. A trade could net Milwaukee a massive haul, including players like Cooper Flagg or Franz Wagner, allowing them to rebuild around younger talent.
However, trading Giannis, a franchise icon who led the Bucks to their first championship in 50 years, would be a painful decision. Some analysts and fans believe he’ll stay, citing his deep ties to Milwaukee and belief in the team’s potential. Yet, with no draft picks until 2031, limited cap space, and Lillard’s contract as dead weight, the Bucks face an uphill battle to build a contender around Giannis before his prime fades.
The Path Forward for the Bucks
The Bucks are at a crossroads. Retaining Giannis requires bold moves, such as trading Lillard’s contract—though finding a taker for $54-$58 million for a 36-year-old recovering from an Achilles injury is unlikely—or overhauling the coaching staff, with some suggesting a replacement for Doc Rivers, whose playoff record has disappointed. Free agents like Brook Lopez and Gary Trent Jr. could depart, further thinning the roster, while player options for Bobby Portis and Pat Connaughton add uncertainty.
Alternatively, trading Giannis could kickstart a rebuild, leveraging his immense trade value to acquire assets for the 2026 draft, projected to feature top prospects like Cameron Boozer and AJ Dybantsa. This path, though, risks alienating fans and delaying contention for years.
Conclusion
Damian Lillard’s signing was meant to elevate the Bucks to championship glory, but his costly contract, injury-plagued tenure, and failure to deliver in the playoffs have instead handcuffed the franchise. The trade has left Milwaukee with a depleted roster, no draft capital, and a superstar in Giannis Antetokounmpo whose talents are being wasted on a team far from title contention. As Giannis’ contract clock ticks, the Bucks must act decisively to rebuild around him or risk losing him to a team better equipped to maximize his prime. The Lillard experiment has been a costly lesson, one that may define the Bucks’ future—and Giannis’ legacy—for years to come.
