Brad Stevens’ wheeling and dealing has begun.

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’ books.

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.

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 Porziņģis, with an eye on alleviating their salary-cap dilemma, according to league sources.

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’s first-round win against Orlando.

As one of the NBA’s best and most versatile defensive guards, Holiday remains a winning player. But he could be 36 — and maybe a step or two slower — by the time Jayson Tatum returns from a torn Achilles. Holiday’s age and contract made him an obvious trade candidate for the Celtics this summer.

In return for Holiday, Boston gets Simons, an offensive-minded guard who turned 26 on June 8. Though it’s not clear yet how the Celtics view Simons as a part of their future, he will give Joe Mazzulla’s 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.

Will Holiday and Henderson fit in Portland?

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 “a great conversation.” 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’ 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 “a great position and a great spot” for him.

“It meant a lot,” Holiday told The Athletic in 2024. “Being 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’t 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.”

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.

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 — one of your supposed pillars — 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?

The Blazers were painfully void of impactful leadership — 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 — defense. Paired with Toumani Camara, Deni Avdija and Donovan Clingan, Holiday and his savvy could elevate Portland from good to great on defense.

This move would seem to indicate the Blazers believe they are ready to compete for a playoff spot, which is ambitious, but likely unrealistic … so did they just clog up their cap space for an aging and expensive player who doesn’t fit their timeline? Or are bigger moves on the horizon?

(Photo: Maddie Meyer / Getty Images)