The Milwaukee Bucks may have considered a stunning move this offseason had circumstances been different. According to a report by ESPN’s Jamal Collier, the franchise was prepared to explore a Damian Lillard trade had he remained healthy: a ‘last-ditch’ strategy to find another co-star for Giannis Antetokounmpo before time runs out on his prime.
Instead, Lillard’s injury recovery threw a wrench into that plan. With Lillard’s status uncertain and Milwaukee already thin on depth, the team pivoted from blockbuster deals to more conservative adjustments.
As one source told ESPN, “When you talk about winning a championship, it takes time. I don’t think they had time to do that."
As Giannis Antetokounmpo applies pressure on the Bucks, there has been increasing doubt about his loyalty. According to the latest reports, he still hasn't made up his mind about continuing his tenure with the Bucks, and the franchise is scrambling to prove they’re still worthy of his commitment. At this point, all they can do is re-earn his trust by making moves that will maximize their title chances.
Ultimately, the Bucks chose to risk everything to maintain their contender status next season, and even if Lillard had stayed healthy for the franchise, it wouldn't have been enough to save his job. After two failed seasons, where they couldn't win a single playoff round, Milwaukee was convinced that the only way to flip their trajectory was to make a drastic move and find a new co-star for their 2x NBA MVP.
With averages of 24.9 points, 4.7 rebounds, and 7.1 assists per game last season, Lillard could have gotten a nice return on the trade market, with teams like the Heat and Trail Blazers standing out as the most likely to strike a deal for the veteran sharpshooter.
But then came the Achilles tear — derailing both their playoff hopes and any trade plans. The Bucks ultimately waived and stretched his contract to free up space for veteran big man Myles Turner.
The Bucks, unwilling to wait, have been busy for weeks remaking their roster and team identity in order to ensure Giannis' loyalty. Besides Turner, they have a solid cast of role-players ready to perform at a high level, including Gary Trent Jr., Kevin Porter Jr., Taurean Prince, Kyle Kuzma, and Bobby Portis.
Only time will tell if it's enough to keep the Bucks relevant in the East, but Giannis is no doubt weighing their title chances as he reconsiders his basketball future. If he doubts their status for any reason, it could lead to a devastating scenario for Milwaukee.
Now back in Portland, Lillard is getting the chance to close his journey where it began, marking a full-circle moment for the franchise legend. His time in Milwaukee may not have lived up to expectations, but it taught him a powerful lesson: the grass isn’t always greener on the other side. As the Bucks move forward with a new identity, Lillard can finally find peace playing for a team that never stopped believing in him.
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