In a surprising turn of events, the Milwaukee Bucks are parting ways with Damian Lillard less than two years after acquiring the star guard. After a season marred by injuries and playoff disappointments, the Bucks have made significant roster changes, signaling the end of the Lillard era in Milwaukee.
Trade and Early Hopes
When the Milwaukee Bucks traded for Damian Lillard in 2023, it marked a pivotal moment in the franchise’s history. Lillard, frustrated with the Portland Trail Blazers—his only NBA home—had sought a trade, ideally to the Miami Heat. However, the Bucks emerged victorious in the bidding war, presenting an exciting opportunity for a lethal offensive pairing alongside Giannis Antetokounmpo.
Injuries and Roster Changes
Despite high expectations, Lillard’s time with the Bucks was plagued by injuries. The team secured the No. 3 seed in the Eastern Conference during his first season, but their playoff run ended abruptly with a first-round exit at the hands of the Indiana Pacers. Lillard’s struggles worsened this past season as he was diagnosed with deep vein thrombosis in his right calf. Although he aimed to return for the playoffs, a torn Achilles tendon in Game 4 of the first round has left him sidelined for the upcoming season.
Following another disappointing playoff performance against the Pacers, the Bucks have opted for significant changes. They signed center Myles Turner away from the Pacers on a four-year, $107 million contract, a move that necessitated waiving Lillard. The financial structure of NBA contracts means that the Bucks will still owe Lillard approximately $113 million, which they can amortize over the next five years using the stretch provision.
Pacers insider Alex Golden reported that Indiana had initially offered Turner a deal worth “well north” of $20 million per year. However, negotiations faltered, leading to Turner’s lucrative contract with Milwaukee, which effectively costs the team $220 million after the release of Lillard.
This abrupt end to Lillard’s tenure in Milwaukee—less than two seasons after his arrival—raises questions about his future. At nearly 35 years old and facing the challenges of recovering from an Achilles injury, Lillard may seek to rebound with another contender, adding intrigue to his next career chapter.

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