Jrue Holiday is headed to the Trail Blazers again. This time, it appears the six-time All-Defensive team selection is a part of Portland’s plan.
Late Monday night, the Celtics agreed to send Holiday to the Blazers in exchange for Anfernee Simons and draft compensation, according to ESPN’s Shams Charania. The deal comes less than two years after Holiday was rerouted from Portland to Boston after being a key part of the deal that sent Damian Lillard to the Bucks.
Holiday, 35, immediately becomes a key veteran for an up-and-coming Blazers team while Simons will provide both a scoring boost and cap relief for the Celtics.
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Here’s how the deal grades out for both sides.
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Jrue Holiday trade details
Trail Blazers receive:
- Jrue Holiday
Celtics receive:
- Anfernee Simons
- Two second-round picks
Trail Blazers trade grade
Quiet as it’s kept, Portland was one of the more pleasantly surprising teams during the 2024-25 season, and the team may be closer to postseason contention than some realize.
With head coach Chauncey Billups leading the way, the Blazers finished with a 36-46 record and were within five games of a Play-In Tournament spot. They’ve also begun to create an identity with a young nucleus headlined by Deni Avdija, Toumani Camara, Donovan Clingan, Scoot Henderson, and Shaedon Sharpe.
Holiday does not exactly fit the young identity, but he is an adult in the room and famously one of the game’s more malleable players. Offensively, he can play on and off the ball, and defensively, still brings it at an elite level, albeit not necessarily as much as he did during his younger days.
Due to that reputation, many immediately noted the scary defensive potential of Holiday and Camara, who earned the first All-Defensive Team selection of his career this past season. Holiday will also be an incredible mentor for Henderson and can be an extension of Billups’ coaching on the court.
Jrue Holiday and Toumani Camara on the same team. Portland’s defense might set a record for 8-second violations next season.
— Mr. Statistician Face Man (@tomhaberstroh) June 24, 2025
Parting ways with Simons creates more room for the growth of Portland’s ball-dominant wings, putting the ball in Henderson and Sharpe’s hands more.
Positives aside, Portland is paying a hefty price for Holiday, who is owed $104.4 million over the remainder of a contract that runs through the 2027-28 season. He is entering his 17th NBA season, and last year, he turned in his lowest statistical output since he was a rookie.
It’s not exactly a lateral move, but it’s also difficult to look past the fact that Portland is taking on more years on a contract of a player who does not fit the franchise’s developmental timeline. The Blazers could eventually move on from Holiday down the line, but the deal is eyebrow-raising in that sense.
This is right on the line of being a B, but there are too many questionable components of it to overlook.
Trail Blazers grade: C+
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Celtics trade grade
There are layers to this deal for the Celtics.
On the court, Boston is headed into a season of uncertainty as All-NBA forward Jayson Tatum will be sidelined indefinitely to rehab his torn Achilles. The Celtics need a scoring punch without Tatum’s 26.8 points per game, and Simons provides that.
Over the past four seasons, Simons is averaging 19.9 points and 4.5 assists per game while shooting 38.1 percent from 3-point range at a high volume. Stylistically, he provides a much different look in Boston’s backcourt, but Simons is set to thrive in Joe Mazzulla’s free-flowing offense, which prioritizes the 3-ball.
Simons is 26, and the Celtics also get much younger with the deal. They’ll have an opportunity to fully assess his fit within the system to decide on his long-term fit in Boston. With the bigger picture in mind, the financial component is the biggest takeaway.
In the trade’s aftermath, ESPN’s Bobby Marks outlined the cap relief the Celtics will receive from the deal. Simons, who is extension-eligible, has just one year and $27.7 million remaining on his contract.
As explained by Marks, the Celtics will save a projected $40 million and are now just $18 million of the second apron of the NBA’s luxury tax. With this in mind, it would appear that this move won’t be Boston’s last of the offseason.
Here are the salaries going out
To Boston
Anfernee Simons: $25.9M, $27.7M (UFA, 2026)
* The Celtics get off the combined $72M owed to Holiday in 2026-27 and 2027-28
* Projected $40M in tax savings in 2025-26
* $18M over the 2nd apron
* Simons is extension eligible
To…
— Bobby Marks (@BobbyMarks42) June 24, 2025
Simons isn’t the perfect fit, but he addresses a need and should thrive in Boston. Between that, the financial relief and the assumption that the Celtics are not done dealing, this is a trade to be encouraged by.
Celtics grade: B
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