Moving Jrue Holiday’s three-year, $104.4 million contract simultaneously became the straightest path to the Celtics downsizing their payroll this summer — and their biggest offseason challenge. Reported suitors like the Mavericks and Clippers faced difficulties in making the money work for a deal, and a Kings roster in flux never sounded like a strong suitor. All along, the chance existed that the Celtics would need to sweeten a trade with draft compensation due to Holiday’s age.
Yet Boston stood firm on the Brad Stevens mantra from his media day. He positioned the Celtics’ roster situation as a strength, they have a lot of great players, and Holiday generated enough of a market to make a team part with assets to acquire him.
The Blazers late on Monday traded Anfernee Simons, a 2030 Knicks second-rounder and their own 2031 second to Boston for Holiday. The Celtics did not need to attach draft compensation to offload him. A win for Boston even if the roster became worse without Holiday.
Trading Holiday for Simons slashed $4.7 million from the $20 million that the Celtics need to reduce their payroll by to avoid the second apron this season. While Boston executed the trade before the end of the 2024-25, the Celtics’ status as a 2025 second apron team finalized at the end of the regular season. This move sets up a second apron reset for 2026, and luxury tax savings that amount to $41 million off their estimated $238.2 million bill if they maintained their current roster. Now, there’s more work to do.
Simons, 26 this season, could move again in another trade. Reports following the Holiday trade indicated Boston’s willingness to begin the season with Simons or assess other deals. Simons is signed for $27.7 million in 2026, just south of Holiday’s salary, but the Celtics cleared Holiday’s $34.8 million deal from their 2026-27 roster and his $37.2 million player option in 2027-28, when he turns 37.
While the Celtics still probably want to shed some salary from their 2025-26 books, they already set up significant flexibility next summer with this move. Simons and Kristaps Porziņģis combine for $58.4-million in expiring money next season. That’s useful for trade flexibility or having the ability to comfortably slide below the luxury tax in two years. That creates less urgency to dodge the tax entirely in 2025-26, though Boston could do that too.
More likely, some combination of Simons, Porziņģis and Sam Hauser moves this week while opportunities emerge closer to the NBA Draft to further downsize the team’s payroll. But Boston also has the flexibility to remain patient with any of those players into the season. If the Celtics keep Simons, he’ll provide a different dynamic than they’ve had in their back court since Kyrie Irving and Terry Rozier patrolled the hard court.
Simons is a shot creator coming off his final Portland season averaging 19.3 points, 2.7 rebounds and 4.8 assists per game while shooting 42.6% from the field and 36.3% from three on 8.5 attempts per game. Over the past three years, Simons took 8.8 threes each night at a 37.4% efficiency. He’s one of the most efficient volume shooters in basketball, finishing 13th in total three-point attempts and tied for 15th with Lauri Markkanen and James Harden, taking 8.5 threes per game. Only Jayson Tatum and Derrick White attempted that many for Boston.
Last season, Simons produced 1.12 points per possession while spotting up, which ranked in the 69th percentile in the NBA. He ran 7.1 pick-and-rolls per game at 0.99 PPP, which finished in the 79th percentile.
Defensively, he struggled, allowing 1.00 PPP in isolation (30th percentile), 1.08 PPP against pick-and-rolls (6th percentile) and 1.04 PPP against spot up shooters (54th percentile). Opponents shot 50.6% against Simons last season, the worst mark of any regular contributor on a Blazers defense that climbed to 16th in defensive rating late last season. Portland ranked eighth defensively over its final 15 games. During that stretch the Blazers still lost Simons’ minutes by 2.5 points per 100 possessions. That could force Payton Pritchard to start in place of Holiday this season.
It also explained the Blazers’ inability to return significant value for Simons beyond salary-matching in this deal, and needed to attach two second-rounders to Boston in the deal. The Celtics’ defensive rating improved by more than 3.0 points per 100 possessions with Holiday on the floor compared to off last season. Portland’s defense worsened by three points per 100 with Simons on the floor. It’s no surprise that Simons, at 6-3, 201 pounds, won’t fit as comfortably into the Celtics’ switching defense as Holiday, one of the all-time great NBA defenders, did.
So the question remains whether Simons fits into what Boston wants to do this season and beyond. They need more offensive creators and athletes to stay afloat this season without Tatum, and like the case for keeping Porziņģis, it wouldn’t be difficult to move an expiring salary in-season if Simons begins the year on the roster. If not, the process toward downsizing salary always involved several steps for Boston. And Simons can return one or multiple players who earn roughly $1-7 million less than what he makes. The Celtics will inevitably operate in those negotiations as they did with Holiday — preferring not to attach picks with him and searching for a legitimately valuable return.
In any Holiday scenario we imagined, Dallas, LA and otherwise, no player as singularly intriguing as Simons came back to the Celtics. Boston not parting with any draft capital, and actually gaining some for the distant future made this a win for Stevens, who tapped back into his relationship with Blazers GM Joe Cronin, who originally sent the Celtics Holiday in 2023 following the Damian Lillard deal.Stevens and Cronin partnered on the Dalano Banton salary dump that helped Portland, and now, the Blazers hope Boston delivered them the player who can help them become a surprise playoff competitor.
While not what he imagined either, the Blazers might prove the best fit for Holiday too, who can defer to Shaedon Sharpe and Scoot Henderson as primary creators while Holiday spaces the floor in role similar to what he played in Boston.
Holiday leaves the Celtics as a 2024 champion, All-Defensive Second Team that year and the author of one of that run’s defining plays to cap the comeback at Indiana that looks all the more impressive after this month’s Finals.
