Jrue Holiday Trade Grades for Boston Celtics, Portland Trail Blazers
It looks like this NBA offseason could be relentless.
Last week, the Memphis Grizzlies traded Desmond Bane to the Orlando Magic. On Sunday, with Game 7 of the Finals looming, Kevin Durant was dealt to the Houston Rockets. And now, just one day after the campaign officially ended, the Portland Trail Blazers are acquiring Jrue Holiday from the Boston Celtics for Anfernee Simons and a pair of second-round picks.
ESPN's Shams Charania had the news first.
At first glance, this feels like a classic win-win move that will save the gap-year Celtics some money, while pushing the up-and-coming Blazers closer to the play-in, but it's hard to know for sure before going to the report card.
Grades for both sides can be found below.
Boston: A
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The motivation here is clear. The moment Jayson Tatum went down with a ruptured Achilles in the second round of the playoffs, Boston's $227.8 million payroll and $238.2 million luxury tax bill (which combined to make the Celtics' roster the most expensive in the league) became untenable.
Boston won't contend without Tatum. And there was no way to justify paying that for a team that won't contend, especially with Holiday post-prime, too.
Trading Holiday's salary ($32.4 million this season) for Simons' ($27.7 million) saves the Celtics $40 million in luxury tax and gets them within shouting distance of being able to duck the second apron line.
That alone probably would've made this a win for Boston, but there are other bonuses here.
Simons is on an expiring contract, which means it could be easier to flip him in a subsequent deal. It also means that if things don't go well and the Celtics can't move their new guard, they can just let him walk in free agency.
On the other hand, Simons is only 26. He's talented. You don't average 19.9 points, 4.5 assists and 3.2 threes, while shooting 38.1 percent from deep, over a four-year stretch in the NBA without that.
If he buys into Boston's team- and defense-first culture, the Celtics may have just turned the clock back on that roster spot by nine years.
Add a couple second-round fliers, and it's easy to hand out this "A" grade. Some potential suitors almost certainly would've insisted on the Celtics being the ones who'd have to give up assets to get off Holiday's contract (which runs through 2027-28, when he has a $37.2 million player option).
Portland: B
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Even though they're the team giving up the younger player and a couple second-round picks, it's mostly upside for the Blazers, too.
Portland likely already made the calculation that it wasn't going to commit a ton of money to Simons in free agency. There's plenty of still-developing talent in the backcourt in Shaedon Sharpe and Scoot Henderson to potentially replace the scoring. And Deni Avdija is clearly ready for more of an alpha role.
This trade makes official what the above just made possible. Simons' free agency is officially off the table, and his replacement won't take many touches and shots from the younger core.
Holiday has proven more than capable of sharing the floor with ball-dominant teammates, hitting open catch-and-shoot opportunities and focusing on defense.
His game will fit easily in Portland, but it may be his leadership and championship experience that proves even more valuable.
In the short term, Holiday can push a team on the fringe over it. The Blazers had an 18-11 stretch from mid-January through mid-March that suggested their ready to contend for, at the very least, a play-in spot. Holiday can help them do that.
So, why aren't they getting an "A" grade, too?
Well, giving up draft assets (multiple) for a 35-year-old guard who just saw his scoring average dip to 11.1 in 2024-25 (and 9.5 in the 2025 playoffs), even if they're second-rounders, isn't ideal.
And perhaps more importantly, Holiday's contract has the potential to age poorly. There are three seasons left. He'll be 38 when it ends (assuming he picks up the $37.2 million option for 2027-28). And in the West, there's no guarantee Portland even makes the playoffs during the life of Holiday's deal.
None of that is enough to drop the Blazers' mark lower than a B, though. The cost isn't prohibitive, and Portland proved worthy of win-now deals toward the end of 2024-25.
