You can trace a lot of what happened next back to one deal. The Milwaukee Bucks sent Jrue Holiday to the Portland Trail Blazers in the 2023 Damian Lillard trade and, according to people inside the organization, that single move unraveled the entire identity of the team.
Holiday was never the loudest star on that 2021 championship roster. But he was the one who made it work. A Bucks source told ESPN’s Ramona Shelburne and Jamal Collier that losing Holiday broke something fundamental.
“Looking back on it, the one thing we did that changed everything was put Jrue in that trade,” the source said. “Jrue was such a leader on and off the floor. He would do things like if Giannis was holding the ball too much, Jrue would just bring it up and play with everybody else without making it a thing. He was a pro at it.”
The logic at the time was simple. The Bucks thought they needed more offense. They needed another scorer alongside Giannis Antetokounmpo. So they swapped a two-way guard for a pure bucket-getter in Lillard. But the math didn’t add up.
“But Jrue was in the deal [for Lillard] because we thought we needed offense over defense. But once he was gone, we lost our whole defensive identity. It’s not so much that getting Dame was a mistake. He would’ve been perfect if we still had Jrue,” the source said.
The Luka Factor and a Star’s Shift
The season after Holiday left, the Bucks couldn’t get out of the first round. They haven’t been back to the Eastern Conference Finals since 2021. Holiday, meanwhile, got rerouted to Boston and won a ring with the Celtics in 2024.
Then the Luka Doncic trade happened in February 2025 and everything changed again. Seeing the Mavericks ship their franchise player to the Lakers without warning made Antetokounmpo rethink everything, according to the Milwaukee Journal Sentinel’s Jim Owczarski.
“In a way, for Antetokounmpo, pushing ownership to its limits flipped the script, verifying the organization’s belief in him. That changed in February 2025 with the surprise trade of Dallas star Luka Doncic to the Lakers, which crystallized in Antetokounmpo’s mind how little real control superstars had,” Owczarski reported. “So, Antetokounmpo began to separate himself. One step was physical. For years, he haphazardly collected his trophies at his suburban Milwaukee home. But in the 2025 offseason, he packed them up and took them to Greece.”
The message was clear. He was done waiting.
What Comes Next
This wasn’t a dramatic exit or a trade demand. It was quieter than that. Antetokounmpo played out his final season in Milwaukee with the understanding that his time there was ending on his own terms. The Bucks never recovered the balance they had with Holiday on the floor. And without that defensive anchor, the foundation just cracked.
Antetokounmpo is set to start a new chapter with the Miami Heat in the 2026-27 season. One trade started all of this. The Bucks knew the risk. They took it anyway.
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