Perhaps the biggest deal of the offseason already went down when the Milwaukee Bucks traded superstar forward Giannis Antetokounmpo and Bobby Portis to the Heat.
The Bucks received Tyler Herro, Kel’el Ware, Jaime Jaquez Jr., Kasparas Jakucionis, three first-round picks (including No. 13 in Tuesday’s NBA draft, which was used on Tennessee forward Nate Ament), one pick swap, and one second-round pick.

Two Mistakes Led to Bucks’ Star Giannis Antetokounmpo’s Trade to Heat
Obviously, the Bucks were hoping to keep the “Greek Freak” in Milwaukee forever, but after missing out on the postseason and fleeting hope they could keep Antetokounmpo, the Bucks finally pulled the trigger on the deal.
It turns out that a disappointing outing from Jrue Holiday, specifically while assigned to Jimmy Butler, may have been the “beginning of the end.”
According to ESPN’s Ramona Shelburne and Jamal Collier, Antetokounmpo wanted to guard Butler during their first-round series in 2023, but because of his bad back, he did not draw the assignment.
“Point guard Jrue Holiday, instead, had drawn that assignment and faltered,” Shelburne and Collier wrote. “Holiday had struggled in back-to-back playoff series, shooting a combined 37% in Milwaukee’s last 12 playoff games.
That frustration led to two fateful decisions that serve as the line of demarcation for the beginning of the end of Antetokounmpo’s time with the Bucks.”
The Bucks went on to lose to the eighth-seeded Heat five games. Although the Heat went on to the NBA Finals, losing to the Nuggets in five games, a one seed losing to an eight seed is never going to sit well with anyone.
Reacting to that loss, the first poor decision the Bucks made, according to Shelburne and Collier, was the firing of Mike Budenholzer, eventually leading to the hires of Adrian Griffin and Doc Rivers.
Budenholzer coached the Bucks from 2018-2023, leading the team to the Central Division title in each season he was in Milwaukee, including the 2021 NBA title. Budenholzer even went 58-24 and earned the top seed in the East, but their first-round loss to the Heat sealed their fate.
He was replaced by first-time head coach Adrian Griffin, who lasted just 43 games and was fired despite a 30-13 start. Veteran coach and former NBA Champion Doc Rivers was then hired to replace Griffin. After this season’s 32-50 finish, Rivers went 97-103 with the Bucs. He resigned following the season.
The next was sending Jrue Holiday to Portland in a deal that brought back star guard Damian Lillard.
Lillard is one of the league’s all-time great shooters and a brilliant player, but injuries, some issues defensively, and overall aging stopped Lillard and Antetokounmpo from becoming the duo the Bucks hoped for.
“Looking back on it, the one thing we did that changed everything was put Jrue in that trade,” a Bucks 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.”
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“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.”
Holiday was then dealt to the Celtics, where he helped them win a championship in 2024 (and is now back in Portland).
At the time, trading for Lillard and firing Budenholzer didn’t necessarily seem like the wrong move, although many questioned the decisions.
With the way things were going in Milwaukee, it may not have mattered much if the Bucks hung on to Budenholzer and Holiday, but you can bet they’d like to go back in time and find out.
