Should Blazers fans be worried about Jrue Holiday’s health after adjusted trade

The last time the Trail Blazers traded for Jrue Holiday, it led to a championship. Not for them, but still! Is there reason to be concerned this time around?
Apr 20, 2025; Boston, Massachusetts, USA; Boston Celtics guard Jrue Holiday (4) has words with crew chief Zach Zarba during the second half against the Orlando Magic at TD Garden. Mandatory Credit: Bob DeChiara-Imagn Images
Apr 20, 2025; Boston, Massachusetts, USA; Boston Celtics guard Jrue Holiday (4) has words with crew chief Zach Zarba during the second half against the Orlando Magic at TD Garden. Mandatory Credit: Bob DeChiara-Imagn Images | Bob DeChiara-Imagn Images

For about half a week in 2023, Jrue Holiday was a Portland Trail Blazer. This was a very big deal. Many people were happy. Some cried, but it was okay because it was the happy kind of crying.

These times did not last long, however, and Jrue was gone as quickly as he came. He won a championship with his new team in Boston. Some say Portland would have won that championship if he stayed. They are wrong.

But sometimes wounds can be healed and relationships can be repaired. Jrue Holiday has once again been traded to the Portland Trail Blazers. Again, there were tears. I haven’t checked the Vegas lottery odds, but I have to imagine Portland is the favorite to win in 2026.

Everything looked great! Rumors came out about Jrue not being happy which is how he shows he’s happy, the Trail Blazers young defenders got a point-of-attack legend to learn from, and, gosh dang it, there was a champion in the building now. Nothing could be better.

But then:

To recap. Jrue Holiday was coming to the Portland Trail Blazers from the Boston Celtics in exchange for Anfernee Simons and two second round picks. After the Blazers did the pretty-gross-to-think-about thing where they medically assess the incoming player’s physical state and potential for deterioration, they decided “Whoops! Body bad!” Suddenly, those two second round picks became too much to include in the deal. Due to a concerning grade on a “what is your physical condition as a human being test,” Jrue was no longer worth those two second-round picks in addition to Anfernee Simons.

It’s weird to think about when it’s all laid out like that.

Is the Jrue Holiday trade news even a bad thing?

One way to look at this was that Jrue and the medical team took issue with this whole process and conspired to make it look like Jrue had Bad Body Syndrome and was therefore a health risk. That way Portland didn’t have to give up as much and Jrue is actually totally fine, guys, trust me. Maybe he was mad at the Celtics for trading him. I don’t know.

We can’t depend on that being true. I think the easier truth to swallow is that even a slightly diminished Jrue is a wonderful player and wonderful person to have on your team. Having the space to take on Jrue’s contract let you be the team that could take advantage of Boston’s crunch under the second apron. Even if Jrue isn’t going to give you 2024 Jrue, or Milwaukee Jrue, he’s going to give you something you wouldn’t have otherwise.

And if this team does turn into something, if it takes another step this year, well, the core that does eventually take the following steps from play-in, to playoffs, to contender probably doesn’t include either Anfernee or Jrue.

I would be very happy for Simons to prove my estimation of him wrong, though. Maybe Boston will make him great.

But getting Jrue Holiday at all was an awesome thing in the first place. Downgrading from “awesome” to “quite awesome” is still pretty awesome.