Right before the start of the 2023-24 NBA preseason, the Milwaukee Bucks made an unexpected roster move. While it had been long known that Damian Lillard wanted to be traded away from the Portland Trailblazers, many assumed that the Miami Heat were his preferred destination. After all, he had said as much. However, weeks turned into months, and Portland turned down every poor offer that Miami made.
Then, out of nowhere, Bucks general manager Jon Horst swooped in and got a deal done, acquiring the now-nine-time All-Star for Jrue Holiday. Grayson Allen was sent to the Phoenix Suns, who were also a partner in the trade.
And as hard as it was for fans to say “goodbye” to Holiday, who had become a favorite due to his incredible work in the community and his contributions to Milwaukee’s 2021 NBA Championship, everyone understood why Horst made the trade: if one can get Damian Lillard, one of the 75 greatest players of all time, one goes out and gets him.
The Milwaukee Bucks Saw Jrue Holiday Rerouted to the Boston Celtics
Jrue Holiday, Milwaukee Bucks, Dalas Mavericks
Sep 24, 2024; Boston, MA, USA; Boston Celtics guard Jrue Holiday (4) talks to reporters during media day at Auerbach Center. Mandatory Credit: David Butler II-Imagn Images
Much to the dismay of Bucks fans, Holiday was not kept by the Trailblazers for very long. They turned around and traded him to the Boston Celtics, one of Milwaukee’s biggest rivals, in exchange for Malcolm Brogdon, Robert Williams, and two first round picks.
In his first season with the Celtics, Holiday averaged 12.9 points as Boston’s fourth scoring option. He had averaged 19.3 points per game in his final season in Milwaukee. And although his scoring plummeted, his overall effectiveness on the court did not. He shot 48/43/83 from the field while also averaging 5.4 rebounds and 4.8 assists per game.
Holiday finished sixth in Defensive Player of the Year voting that season, was named Second Team All-NBA Defense, and helped the Celtics win the NBA Championship.
After his initial season with Boston, Holiday received a four-year $134.4 million contract extension, indicating that the Celtics viewed him as a long-term piece of their franchise.
But that did not turn out to be the case.
Milwaukee Bucks General Manager Jon Horst Gets Criticized After Jrue Holiday Traded Again
Milwaukee Bucks, Jrue Holiday
Mar 29, 2023; Indianapolis, Indiana, USA; Milwaukee Bucks guard Jrue Holiday (21) dribbles the ball while Indiana Pacers forward Aaron Nesmith (23) defends in the second quarter at Gainbridge Fieldhouse. Mandatory Credit: Trevor Ruszkowski-USA TODAY Sports
As fans are well aware by now, Holiday was just traded by the Celtics back to Portland for Anfernee Simons and two first round picks.
There is no getting around the fact that, as great of a person that Holiday is, he is entering the third year of his monster contract and will be 35 years old when this next season starts. Many are wondering how Boston was able to get so much compensation back for a $30+ million a year player who averaged just 11.1 points, 4.3 rebounds, and 3.4 assists per game.
Additionally, many Bucks fans are wondering why Horst could not have pulled off something like this:
Brad playing 8D chess and Horst is still trying to read Goodnight Moon front to back without starting over. https://t.co/4YAAyXPoNu
— Trey (@TA1297) June 24, 2025
I’m convinced Horst just suffers from a skill issue. Boston makes this look easy. Horst backs himself into corners.
— Jonathan Gauthier (@jgauthier_23) June 24, 2025
We need Horst to enroll in the Brad Stevens school of gaslighting and scamming
— DT (@DBucksFanT) June 24, 2025
bro….. horst go get poole NOWWWW https://t.co/ZzoL9E3bhq
— bringjphome (@bucksinfour) June 24, 2025
Of course, the NBA offseason just officially started, and there is a long way to go. Horst has proven that he is not shy about making big moves, but considering the Bucks have been eliminated in the first round in each of the last three postseasons, one can understand why fans are frustrated.
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