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History of Brad Stevens' biggest trades as Celtics exec

Brad Stevens was a great head coach for the Boston Celtics. But you could make an argument he's been an even better executive for the franchise.

Stevens moved from head coach to president of basketball operations in June of 2021, and he has excelled in that job, most notably putting the finishing touches on a championship roster for the 2023-24 NBA season.

After the Celtics lost at home to the Miami Heat in Game 7 of the 2023 Eastern Conference Finals, Stevens made two bold moves in the following months -- acquiring point guard Jrue Holiday and center Kristaps Porzingis.

The Porzingis deal saw fan favorite Marcus Smart depart Boston. It was a tough blow to lose Smart, but Stevens has shown an impressive ability to put emotions to the side and make the moves that are best for the team.

Both Holiday and Porzingis played key roles for the Celtics during their run to the 2024 NBA Finals, where they defeated the Dallas Mavericks in five games to claim the franchise's 18th championship.

But those weren't the only major moves Stevens made that helped put together Boston's title-winning squad.

His first major trade as a Celtics exec happened in June of 2021 when he acquired Al Horford, Moses Brown and a second-round pick for Kemba Walker, a first-round pick and a second-round pick. The C's were able to shed Walker's high salary and contract, and the return of Horford -- who played in Boston from 2016-17 through 2018-19 -- helped the team's outside shooting, defense and leadership in a profound way.

Stevens made a surprise move at the 2022 trade deadline to acquire guard Derrick White from the San Antonio Spurs. White has become a very reliable 3-point shooter and defender. He has a great all-around skill set and has shown tremendous improvement since joining the C's. He also was a huge factor in the Celtics' title run in 2024.

Not every move Stevens has made could be viewed as a home run -- although his batting average is pretty strong.

Trading for Malcolm Brogdon made sense in the summer of 2022, when the C's gave up a first-round pick, Aaron Nesmith and other assets to get the veteran guard from the Indiana Pacers. Brogdon won Sixth Man of the Year in his first season with the Celtics, but an injury limited his effectiveness in the 2023 playoffs. Nesmith has become a good 3-and-D wing for the Pacers, who just lost to the Oklahoma City Thunder in Game 7 of the 2025 NBA Finals.

The latest major trade Stevens has pulled off came Monday night, when he reportedly sent Holiday to the Portland Trail Blazers for Anfernee Simons and two second-round picks. The deal saved the C's about $5 million as they attempt to get under the second apron of the luxury tax.

The Celtics still need to shed about $18 million in salary to get under the second apron. What other moves could Stevens make? The next few weeks could be exciting for basketball fans.

Here's a full recap of Stevens' most notable trades as Celtics president of basketball operations.

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