The Athletic Gives Trail Blazers A “C” Grade For Jrue Holiday Trade

750 The Game Staff The Trail Blazers made a splash late Monday night with the trade of...

The Athletic Gives Trail Blazers A “C” Grade For Jrue Holiday Trade

NEW YORK, NY - MAY 16: Jalen Brunson #11 of the New York Knicks handles the ball while Jrue Holiday #4 of the Boston Celtics plays defense during the game during Round Two Game Six of the 2025 NBA Playoffs on May 16, 2025 at Madison Square Garden in New York City, New York. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and or using this photograph, User is consenting to the terms and conditions of the Getty Images License Agreement. Mandatory Copyright Notice: Copyright 2025 NBAE (Photo by Brian Babineau/NBAE via Getty Images)

750 The Game Staff

The Trail Blazers made a splash late Monday night with the trade of Anfernee Simons and a pair of second-round picks for Boston Celtics guard Jrue Holiday.

Most public conversation around the trade has been skeptical of Portland’s strategy with this trade. While Simons was entering the final year of his contract and Portland was unlikely to re-sign him, Holiday is 35 years old and expensive, with two years and a player option remaining on his current contract worth over $110 million.

The Athletic’s NBA writer Zach Harper wrote on the trade and handed a “C” grade to the Trail Blazers.

I … do not understand this trade for the Blazers. It’s possible they just didn’t see a future with Simons. Maybe he didn’t want to sign an extension there. Perhaps they didn’t think he fit into a defensive mentality they seemed to occasionally form last season. Maybe they wanted to open up more minutes for Shaedon Sharpe. The keys could now be fully handed over to Scoot Henderson, who played well in the second half of last season. Regardless, sending out Simons and two second-round picks so you have the privilege of paying a 35-year-old Holiday $32.4 million for the 2025-26 season, $34.8 million the following season and then praying his 37-year-old self doesn’t pick up a $37.2 million player option in 2027 confounds me.

If the Blazers received a pick in the deal, I would better understand it. Instead, though, they took on more salary for a player who looked like he was breaking down last season. If Holiday can bounce back, it’s a great addition. He can teach Henderson a lot and pair nicely with him. He can still knock down shots and lock down scorers when he’s healthy. But he’s missed 63 games over the last four seasons, including 20 last season.

Maybe the Blazers believe Holiday will get healthy and look great on the floor before they can flip him again? It worked well last time, but the contract, age and health seemed much more attractive to potential trade partners in that instance. Losing Simons isn’t necessarily a bad thing. He’s a good player, but he’s not someone you have to keep forever. I just don’t know if this version of Holiday is the guy you give that up for.

Grade: C