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Reaction To Jrue Holiday-Anfernee Simons Trade

June 24th 2025 at 8:08pm CST by Dana Gauruder

The Celtics pulled off a tremendous swap by not only getting off of Jrue Holiday‘s contract but also getting draft capital in return, John Hollinger of The Athletic opines.

Holiday has three years and $104.4MM left on his deal and it was fair to wonder whether the Celtics would have to attach a first-round pick or two to deal him, Hollinger writes. Instead, they’ll receive Anfernee Simons and two second-rounders from the Trail Blazers.

Boston could extend Simons’ deal — he’s got one year left on his contract, Hollinger notes. It’s also quite possible Simons could be flipped for a player with a lower cap hit as Boston looks to continue shedding salary. The Celtics reached an agreement on another cost-cutting deal on Tuesday, dealing Kristaps Porzingis to the Hawks in a three-team deal that will drop them under the second tax apron.

On the flip side, Hollinger believes this is a baffling move for Portland. The Blazers could have spent another year acquiring young talent and developing players. Instead, they’re trading one of their key sources of offense and handing the point guard duties to Scoot Henderson, who has struggled through his first two seasons.

Aaron Fentress of The Oregonian believes top executive Joe Cronin and coach Chauncy Billups are now in a must-win situation with an ownership change looming (Twitter link). The acquisition of Holiday could help the team reach the postseason and his long-term contract is irrelevant to the current regime, Fentress suggests, since Cronin and Billups might not survive an ownership change if the franchise endures another losing campaign.

The Trail Blazers don’t view themselves as a rebuilding team anymore, according to Sean Highkin of The Rose Garden Report (Substack link), who notes that making the postseason was a stated goal when Cronin and Billups received contract extensions after the team won 23 of its last 41 games.

According to Highkin, Holiday is the type of player that Billups has pined for since Damian Lillard was dealt. Holiday is not only a tough, defensive-minded guard but will provide much needed leadership in the locker room.

Highkin also points out that Cronin effectively picked Henderson over Lillard two years ago by drafting him with the No. 3 overall pick and is now choosing Henderson over Simons. Additionally, Highkin believes Holiday will be more willing to come off the bench behind Henderson than Simons would have been during his walk year, though Fentress (Twitter link) expects Holiday to end up in the starting lineup.

Finally, it’s worth noting that Steve Bulpett of Heavy.com has a source who claims Holiday is upset about being sent to Portland.

“If he winds up staying there, I’m sure he’ll be the professional he’s always been and make a positive contribution,” that source told Bulpett. “But he’s not happy with this deal. I’ll be surprised if Portland doesn’t move him on if they can, because right now he does not want to go there. I’m sure if he has to go to Portland, he’ll end up going and it’ll be OK, but right now they want to be somewhere else. But with that contract, it’s not going to be that easy.”

The idea that the Blazers would give up multiple draft picks to acquire Holiday only to try to trade him to another team doesn’t really pass the smell test, nor does it align with the reporting in the past 24 hours. We’ll see if any other reports corroborate the claim that Holiday is unhappy about the deal, but for now, the comments from Bulpett’s source can probably be taken with a grain of salt.

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