Brad Stevens\u2019 wheeling and dealing has begun.<\/p>\n
In their first trade of what promises to be an active offseason, the Boston Celtics agreed Monday to send Jrue Holiday to the Portland Trail Blazers for Anfernee Simons and two second-round picks, league sources confirmed to The Athletic. The deal, which will save Boston about $4.7 million in salary next season, will also clear significant future salary off the Celtics\u2019 books.<\/p>\n
Holiday still has three years and $104.4 million left on his contract, including a player option for the 2027-28 season. Simons will be on an expiring contract of $27.7 million next season.<\/p>\n
Even after the move, the Celtics still need to trim nearly $20 million to get under the second luxury tax apron and another $20 million beyond that to escape the luxury tax entirely. Because of that, league sources believe the Holiday trade will be only the first domino to fall for Boston. The Celtics are still shopping other players, including Kristaps Porzi\u0146\u0123is, with an eye on alleviating their salary-cap dilemma, according to league sources.<\/p>\n
That salary-cap dilemma was a significant factor in their decision to trade Holiday, 35, who helped deliver a title during his first season with the Celtics but encountered offensive slippage during his second. His scoring and assist averages dropped. His 3-point shooting dipped from 42.9 percent to 35.3 percent. After stepping up during the 2024 playoffs, he averaged just 9.5 points per game in the 2025 postseason. A hamstring injury sidelined him for the final three games of Boston\u2019s first-round win against Orlando.<\/p>\n
As one of the NBA\u2019s best and most versatile defensive guards, Holiday remains a winning player. But he could be 36 \u2014 and maybe a step or two slower \u2014 by the time Jayson Tatum returns from a torn Achilles. Holiday\u2019s age and contract made him an obvious trade candidate for the Celtics this summer.<\/p>\n
In return for Holiday, Boston gets Simons, an offensive-minded guard who turned 26 on June 8. Though it\u2019s not clear yet how the Celtics view Simons as a part of their future, he will give Joe Mazzulla\u2019s team another dynamic playmaker and dangerous 3-point threat. Simons, who averaged 19.3 points and 4.8 assists per game last season, is a 38.1-percent career 3-point shooter. He has graded out as a poor defender throughout his career, which might have been one of the reasons Portland moved on from him. The Blazers have another young guard in Scoot Henderson and envision Holiday helping him both on and off the court.<\/p>\n
Will Holiday and Henderson fit in Portland?<\/p>\n
The Trail Blazers briefly acquired Holiday in the 2023 trade that sent Damian Lillard to Milwaukee, but redirected Holiday to the Celtics less than a week later. During the brief period Holiday was technically on the Portland roster, he and Chauncey Billups connected over what Billups has called \u201ca great conversation.\u201d Billups, who was traded by the Pistons four years after helping them win the 2004 championship, helped Holiday deal with getting blindsided by the Bucks\u2019 decision to trade him. During that chat, Holiday also expressed that he would prefer to be moved to a contender. Billups wanted to help the veteran reach \u201ca great position and a great spot\u201d for him.<\/p>\n
\u201cIt meant a lot,\u201d Holiday told The Athletic in 2024. \u201cBeing able to see a coach that has my best interests (in mind). And you could see it and you could hear it, which a lot of times maybe some players don\u2019t get a chance to see that from a coach. So he definitely had my best interest (at heart) from the beginning. And he just always looked out for me.\u201d<\/p>\n
This time, the Blazers appear to intend to keep Holiday, and he could help them with his defense and leadership. Dealing away Simons also appears to clear the path for Henderson, the third pick in 2023, who only started 10 games in his second season. Simons started all 70 games he played.<\/p>\n
On the other hand, it is a curious move for Portland to take on that much money ($104 million over the next three seasons) at a position where Henderson \u2014 one of your supposed pillars \u2014 is itching to start and take on a bigger role. Are the Blazers paying that much for a mentor? Or do they have reservations about Henderson being ready to take the reins?<\/p>\n
The Blazers were painfully void of impactful leadership \u2014 their two veteran leaders (Jerami Grant, Anfernee Simons) were introverts, and Holiday brings championship experience and a respected voice. He also adds to what is a developing identity of these Blazers \u2014 defense. Paired with Toumani Camara, Deni Avdija and Donovan Clingan, Holiday and his savvy could elevate Portland from good to great on defense.<\/p>\n
This move would seem to indicate the Blazers believe they are ready to compete for a playoff spot, which is ambitious, but likely unrealistic \u2026 so did they just clog up their cap space for an aging and expensive player who doesn\u2019t fit their timeline? Or are bigger moves on the horizon?<\/p>\n
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