Milwaukee Bucks got Damian Lillard in 2023 by letting Jrue Holiday go but the Portland Trailblazers decided to trade him to the Boston Celtics where the latter won his second championship.
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Feb 6, 2023; Portland, Oregon, USA; Portland Trail Blazers guard Damian Lillard (0) drives the lane against Milwaukee Bucks guard Jrue Holiday (21) in the second half at Moda Center. Mandatory Credit: Jaime Valdez-USA TODAY Sports
The Celtics failed to defend their title after they exited in the second round in the hands of the New York Knicks. Rebuilding for them has started and first casualty is Holiday who will now join the team he was first traded to by Milwaukee.
Shams Charania announced that the Celtics have traded the two-time All-Star to Rip City for Anfernee Simons and two second-round picks.
Portland makes an aggressive move to re-acquire Holiday, who the franchise originally received from Milwaukee in the Damian Lillard trade in 2023 and later moved to Boston for a deal that included two first-round picks to Blazers. Simons joins Boston on an expiring contract. https://t.co/2TMs5Cd8qn
— Shams Charania (@ShamsCharania) June 24, 2025
Anfernee Simons vs Boston Celtics
Mar 23, 2025; Portland, Oregon, USA; Portland Trail Blazers guard Anfernee Simons (1) dribbles the ball during the first half against Boston Celtics forward Jayson Tatum (0) at Moda Center. Mandatory Credit: Troy Wayrynen-Imagn Images
The Cs probably got better with this move through a young scoring guard. He is expected to have a featuring role in Joe Mazzulla’s offense with the absence of Jayson Tatum who will only join the team by the latter part of the next season.
Jrue Holiday’s awful end to Celtics stint
The 2024-25 season is statistically the worst season Holiday has had since his rookie year when he averaged just around eight points per game.
He averaged only 11 points per game and career’s second-worst 3.9 assists per game. In the playoffs, he was not much of a threat.
Although the team failed to go for back to back titles, he thought the team is still good enough to contend.
Jrue Holiday, Boston Celtics, Milwaukee Bucks
Nov 10, 2024; Milwaukee, Wisconsin, USA; Milwaukee Bucks forward Giannis Antetokounmpo (34) and Boston Celtics guard Jrue Holiday (4) reach for a loose ball in the fourth quarter at Fiserv Forum. Mandatory Credit: Benny Sieu-Imagn Images
Jrue Holiday said he wants to stay with the Celtics and believes their championship window remains open. Stressed how much talent they have not just on the roster, but on the coaching staff and all the way up to Brad Stevens.
— Jay King (@ByJayKing) May 17, 2025
Holiday, who was part of the Bucks’ 2021-title winning team, will join a team that is stuck in rebuilding mode from being a top player in a legit title contender.
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