The Boston Celtics and Portland Trail Blazers have agreed to a trade that will send Jrue Holiday to Portland in exchange for Anfernee Simons and a pair of second-round picks, reports Shams Charania of ESPN.

The second-rounders going to Boston will be the Knicks’ 2030 pick and the Trail Blazers’ own 2031 selection, according to Jake Fischer of The Stein Line.

The move comes less than two years after the teams got together to make a trade, sending Holiday from Portland to Boston in October 2023. In that deal, the Blazers, who had just acquired Holiday from the Bucks in the Damian Lillard blockbuster, acquired Malcolm Brogdon, Robert Williams and two future first-round picks from the Celtics.

Holiday helped the Celtics win a championship in 2024, but had seen his role dialed back significantly since arriving in Boston, having taken a back seat offensively to higher scorers like Jayson Tatum, Jaylen Brown, Derrick White, Kristaps Porzingis and even Sixth Man of the Year Payton Pritchard.

In 2024-25, Holiday averaged just 11.1 points per game, his lowest mark since his rookie year in 2009-10. He also contributed 4.3 rebounds, 3.9 assists and 1.1 steals in 30.6 minutes per night, along with a .443/.353/.909 shooting line in 62 outings (all starts).

Given Holiday’s relatively modest role in Boston and a contract that will pay him $32.4M next season and $104.4M in total over the next three years, he was considered a strong trade candidate this summer for a Celtics team looking to reduce its payroll.

Boston will do just that in this deal, as Simons is on track to earn approximately $27.7M in 2025/26, which is the final year of his contract. Although that’s only about $4.7M less than what Holiday will make, the swap will generate a projected $40M+ in tax savings for the Celtics, notes ESPN’s Bobby Marks. Boston is deep in luxury-tax territory and will face more punitive “repeater” taxpayer penalties next season.

The Celtics are still projected to be about $18M above the second tax apron for 2025-26, per Marks, but they continue to engage in trade discussions involving other players on their roster, sources tell Charania, so more cost-cutting moves are likely coming.

Besides saving some money in the trade, Boston will add a talented 26-year-old guard in Simons, who has averaged 19.9 points and 4.5 assists per game with a .436/.381/.901 shooting line over the past four seasons in Portland since taking on a featured role with the club. Simons should help make up some of the offense the Celtics lost when Tatum went down this spring with an Achilles tear that is expected to sideline him for most or all of next season. Simons will also be eligible to sign a contract extension with the C’s beginning in July.

The Blazers, meanwhile, will bring in a defensive-minded veteran who will help shore up the team’s perimeter defense while serving as a veteran mentor for Scoot Henderson and Shaedon Sharpe, two young guards still on their rookie scale contracts. Holiday turned 35 earlier this month, and the back end of his contract could become cumbersome, but Portland presumably believes he can help the team take another step forward after it improved from 21 wins in 2023-24 to 36 victories this past season.

Assuming the trade doesn’t expand to include additional pieces, the Blazers will become hard-capped at the first tax apron for the 2025-26 league year as a result of taking back more salary than they send out in this deal. The team projects to be roughly $6.6M below the luxury tax line and $14.7M below the first apron once the move is finalized, notes Keith Smith of Spotrac.

The Sacramento Kings, Toronto Raptors and Dallas Mavericks were among the other teams who had interest in Holiday, reports Jared Weiss of The Athletic. They’ll have to look elsewhere for point guard help now, as the Blazers intend to hang onto Holiday in the hopes of making a push for a playoff spot next season, per Fischer.