A shocking twist in Damian Lillard’s saga has emerged — and it has Milwaukee fans buzzing. According to a prominent NBA insider, Lillard had quietly hoped to end up with the Bucks all along, even before the blockbuster trade that sent him from the Portland Trail Blazers to Milwaukee last season. Now, as Lillard’s $141 million contract extension looms large, it appears the move was more calculated than chaotic.
The insider claims Lillard saw Giannis Antetokounmpo as the perfect co-star to chase his long-coveted NBA title. While publicly loyal to Portland for years, Lillard reportedly communicated to those close to him that Milwaukee’s competitive core, combined with its small-market appeal, aligned perfectly with his playing style and long-term goals.
The Bucks acquired Lillard in a three-team deal last year, with the Blazers securing future assets and Deandre Ayton in return. But the narrative is changing. This wasn’t just a trade — it may have been Lillard’s endgame.
With Lillard’s deal guaranteeing him $141 million through 2027, the Bucks are betting big on the duo of Dame and Giannis. And if this insider report is true, Lillard might have been betting on Milwaukee all along.