The Milwaukee Bucks’ decision to waive and stretch veteran Damian Lillard’s contract over the next five years came as a shock to many. But not to Skip Bayless. After Lillard was brought in as a proven costar alongside Giannis Antetokounmpo, the Bucks have done nothing but underperform. Injuries have certainly played a large factor, but more was expected from this pair of future Hall of Famers. With Dame already sidelined for the entirety of next season, Bayless wasn’t surprised that Milwaukee cut ties with him.
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There was no avenue for Milwaukee to recoup the assets it gave up for the former Portland Trail Blazer. But by spreading Lillard’s contract out over several more years, the franchise was able to scrounge up enough cap space to make a game-changing replacement. Myles Turner is a very different player from Dame, but he’s undoubtedly among the most valuable talents in his position.
Skip explained that the Bucks essentially swapped Lillard for Turner, disregarding the ramifications the move could have in the future. Right now, Milwaukee’s most pressing priority is keeping the face of the franchise happy. Considering Giannis has kept quiet throughout free agency, it seems the Bucks are doing just that.
“You know and I know Giannis signed off on this,” Bayless said on his show. “In the end, all the Bucks management really cares about is keeping Giannis in Milwaukee. And obviously, Giannis did not love playing with Dame. Did you happen to notice what happened the last few weeks of the regular season when Dame was out? He went MVP-style crazy.”
The longtime sports personality has a point. When Lillard first joined the Bucks, he struggled not only to fit into his role but also to fit into his new home. It took some time for the nine-time All-Star to acclimate to his new surroundings. Still, there was no doubt that Dame was helping the Bucks when healthy. He was an All-Star in both of his seasons with the team, after all.
But regular season dominance is no longer enough for Antetokounmpo, who got his first taste of championship glory in 2021 and hasn’t come close to savoring it again since. At 30 years old, Giannis is in the prime of his career and prioritizes winning over all else.
“And when [Dame] and Giannis were on the floor together, that team just never had the look of a contender,” Skip continued. “Obviously, they didn’t win even one playoff series together in two years. They just never really clicked. They never quite fit together. And by the way, you heard that here first. I first guessed that before it ever started.”
Given that most of the team’s championship core was either gone or past its prime, Milwaukee recognized the need for change. By moving on from Lillard and swapping Brook Lopez for Turner, the Bucks have quickly assembled a younger roster. The key question now is whether that youthful infusion can reverse a trend of several disappointing playoff runs.
Adding Turner alone won’t be enough to push Milwaukee back into title contention. Aside from him and Giannis, the roster is largely made up of inconsistent role players. If the Bucks want to reestablish themselves as contenders and keep their franchise cornerstone, the front office will need to further take advantage of their newly freed-up financial flexibility.
