The Boston Celtics started retooling their roster Monday night when they reportedly traded veteran guard Jrue Holiday to the Portland Trail Blazers in exchange for Anfernee Simons and a pair of second-round picks.

After getting eliminated in the Eastern Conference semifinals and watching Jayson Tatum rupture his Achilles, the Celtics front office knew they would have to undergo some significant changes in an effort to avoid the second apron of the NBA’s new salary cap.

That started with trading Holiday, whose salary simply became too expensive for Boston’s liking. In exchange, they got a talented offensive guard in Simons, and assuming he sticks with the team, he will help replace the scoring production that will be missing during Tatum’s absence.

Losing Holiday is undoubtedly a tough blow for the C’s. His ability to operate as an efficient scoring option behind guys like Tatum, Jaylen Brown, Kristaps Porzingis, and Derrick White was part of what made the team so tough to defeat, and even as he prepares to enter his age-35 season, he’s still one of the best perimeter defenders in the game.

Even though he was only with Boston for two seasons, Holiday’s legacy is set in stone thanks to his contributions on the 2024 Finals team. While he reportedly is not happy to have gotten traded to the Trail Blazers, Holiday issued a heartfelt three-word message on Thursday.

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“Thank you, Boston,” Holiday captioned the photo of himself celebrating the second championship of his career.

Holiday averaged 11.1 points, 4.3 rebounds, and 3.9 assists per game for the Celtics last season while shooting 44.3% from the field. While his numbers declined during his time with Boston, he could be set to take on a bigger role in Portland’s offense moving forward.

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In a perfect world, Holiday would have finished his career with the C’s, but the new salary cap forced the team into some tough decisions. Trading away one of the top two-way guards in the league was one of those decisions, and there may be more to come with the offseason just getting underway.

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Featured image via Eric Canha/Imagn Images