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The new CBA has claimed another victim in the Boston Celtics, as they decided to trade Jrue Holiday away to the Portland Trail Blazers for Anfernee Simons and two second-round picks with the primary intention of cutting costs and ducking a huge luxury tax bill for next season.
This trade will have plenty of ramifications for both the Celtics and Blazers, two teams that are far from done wheeling and dealing this offseason. But this trade at least signals that Boston is, indeed, pivoting in a different direction, perhaps looking at the 2025-26 season as a bit of a gap year amid Jayson Tatum's recovery from an Achilles injury.
Meanwhile, the Blazers, after a strong finish to last season, appear to be gearing up for a playoff push in 2026, provided, of course, that Holiday remains on the roster and isn't re-routed. Whatever the case may be, here are some immediate trade grades for the teams involved in this stunning trade.
Celtics come out as a huge winner
Even without the crushing Tatum injury, there was already talk about how the Celtics were going to cut costs and attempt to duck under the second tax apron due to the punitive nature of the new CBA. If the Celtics were to run it back, they were at risk of footing a player payroll worth around $500 million due to tax penalties.
Any billionaire owner would already balk at that exorbitant amount. But now that the Celtics are under new ownership, the likelihood of them selling off some of their core pieces went through the roof. It then became a foregone conclusion when Tatum went down, as without him, it was unlikely for Boston to compete for a title anyway — making it rather impractical to foot a bill worth nearly half a billion for a team that, at best, could make it to the second round.
With that, Holiday loomed as a big potential casualty. His production has declined a lot (he put up 11.1 points, 4.3 rebounds, and 3.9 assists last season — with his scoring average being his lowest since his rookie year) and even with him taking a smaller role on offense, his efficiency still dropped.
At 35 years of age, it was fair to wonder just how much gas Holiday has left in the tank. Defense is his calling card, but as he ages, his athleticism declines as well, and with declining athleticism means that he's less capable of defending speedier and stronger ballhandlers on the perimeter.
That alone made Holiday an expendable piece for the Celtics. In a world where Tatum didn't injure his Achilles, it still would have been justifiable to trade Holiday because of those reasons. They had Payton Pritchard, reigning Sixth Man of the Year, anyway to fill in the backcourt void that Holiday's potential departure would have created.
But Holiday's contract relative to his production makes it all the more necessary for the Celtics to trade him away. Holiday was set to make a total of around $110 million over the next three seasons, taking him up to his age-37 campaign, and he's already in decline. That contract could be really bad as soon as the upcoming season or perhaps the next, making it difficult for Boston to trade him had it gone to that point.
So for the Celtics to not just be able to trade Holiday away, but to do so for Simons, whose contract is expiring at the end of next season, and two second-round picks? That is a big win for Boston.
It looked like the Celtics even had to attach draft capital just to get off of his contract. But instead, they have a clean pathway to shedding even more salary (Simons' expiring contract would be easy to trade to another team) and have managed to get Holiday's onerous contract off the books, all while grabbing more draft capital (even second-rounders have value) in one fell swoop.
The Celtics may not have been able to repeat as champion. But they have the front office capable of gearing up for another title push once Tatum is back to full health and this trade just proves that even further.
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Grade: A
Blazers look to take the next step
Making the leap from bad team to potential playoff contender is tough. Bringing in veterans to help establish a winning culture helps in that regard, however. For the Blazers, they seem to be replicating the step the Houston Rockets took when they brought in Dillon Brooks and Fred VanVleet by trading for Holiday.
Holiday, at this point of his career, is a huge offensive downgrade from Simons. Even then, Holiday, even in his declined state, defends much, much better than Simons could even dream about. This trade also opens up a spot for Scoot Henderson to perhaps finally seize the mantle as the team's point guard of the future, with Holiday providing the necessary veteran leadership that could help take a Blazers team that won 36 games last season and push them above the .500 mark.
This trade clogs the Blazers' cap sheet, and they're already stuck with one of the worst contracts in the NBA in Jerami Grant's. But it's not like the Blazers are about to pay a ton to keep their core together. They have future cap room, especially with Deandre Ayton in the final year of his contract, while Matisse Thybulle's deal is set to expire at the conclusion of this upcoming season as well. Shaedon Sharpe will be up for an extension, but he shouldn't break the bank too much anyway.
Thus, this trade should be a win for the Blazers as well. They managed to parlay Simons, who wasn't guaranteed to stay anyway upon the expiry of his contract in 2026, into the quintessential winning player in Holiday.
Moreover, Holiday, despite his huge cap hit over the next three seasons, remains valuable in the eyes of teams with contending aspirations, and rightfully so, since he does all the dirty work, defends like his life depends on it and doesn't ask for all the glitz and glamour. Thus, if the Blazers decide that rerouting Holiday is the best course of action, they should still get something of value for the veteran.
This may not be a huge, huge win for the Blazers, but it's hard to fault their reasoning for making this trade.
Grade: B+
