Boston Celtics depth chart after franchise trades Jrue Holiday for Anfernee Simons and draft compensation

The Boston Celtics traded fan favorite Jrue Holiday to the Portland Trail Blazers on Monday for Anfernee Simons and two second-round picks, per NBA insider Shams Charania. Celtics president Brad Stevens retooled the roster by trading a veteran for a younger star who could re-energize the team. Simons joins a core that still includes Derrick White, Jaylen Brown and Jayson Tatum.

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Stevens managed to shed Holiday's $32.4 million salary for next season to take on Simons' $27.6 million contract. The Celtics, though, will likely give the 26-year-old guard an extension as he becomes an unrestricted free agent after the 2025-26 campaign.

Here is the Celtics' depth chart after the Holiday-Simons swap.

Anfernee Simons takes over Jrue Holiday's starting guard spot on the roster and forms a new backcourt duo with Derrick White. Sixth Man of the Year winner Payton Pritchard comes off the bench for the Boston Celtics. Jaylen Brown, who has played small forward for most of the past two seasons, keeps his spot.

Jayson Tatum's recovery from Achilles surgery could keep him out to start the 2025-26 season. When he's ready, he should return to his usual starting power forward role besides Kristaps Porzingis if Brad Stevens keeps the 7-foot-3 Latvian.

Stevens reportedly wants the Boston Celtics to drop under the punishing second apron. If that rumor holds true, Holiday's trade could just be the start. Boston is still $18 million over the second apron after swapping Holiday for Simons, per Spotrac.

Shams Charania reported roughly a week ago that Stevens looked at Holiday, Porzingis ($30.7 million) and Sam Hauser ($10.0 million) as trade chips. With the veteran point guard gone, the two could follow.

The Boston Celtics sent Jrue Holiday back to Portland

Jrue Holiday's three-year, championship-winning stint in Milwaukee ended in the summer of 2023 when the Bucks traded him to the Portland Trail Blazers. The move happened after the Bucks went after former Blazers superstar Damian Lillard.

Holiday's stay with the Blazers did not even last for a few weeks. The Boston Celtics sent Malcolm Brogdon, Robert Williams and two future first-round picks (2024, 2029) for Holiday. Brad Stevens' decision immediately paid off as Jrue Holiday played a key role in the Celtics' 2024 championship run.

On Monday, Stevens sent him back to Portland for a younger, more athletic guard.

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About the author

Michael Macasero

Michael Macasero brings a wealth of knowledge and expertise to his coverage of basketball at Sportskeeda with over 18 years of diverse work experience. This includes stints at Convergys, Interpace and RunRepeat.

Michael's background in English and Journalism has provided him with the analytical skills and precision necessary for creating content, and he is a lifelong fan of the Boston Celtics. His favorite players include legends like Larry Bird and Michael Jordan, modern stars like Tim Duncan, and Nikola Jokic, as well as emerging talent like Victor Wembanyama.

Michael respects Gregg Popovich, despite his contentious demeanor in interviews, and recognizes Popovich's genius in adapting his coaching style to maximize the talent on his roster over the years. Michael eagerly anticipates seeing how Popovich will structure the offense around emerging talent like Victor Wembanyama.

Understanding the story and details is crucial to Michael's reporting philosophy and he believes overlooking details, particularly when pressed for time, can lead to misunderstandings and inaccurate conclusions.

Aside from work, Michael's children are his hobbies, and he also likes to go running, swimming and weightlifting.

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