Bill Simmons and Ryen Russillo recently covered "The Bleakest NBA Team Situations" over the next five years on The Bill Simmons Podcast. The good news for Trail Blazers fans is that Portland didn't make Simmons' top-five ranking in the Western Conference.
But the bad news is that the Blazers didn't do themselves any favors regarding their long-term outlook when they surprisingly traded for Jrue Holiday.
"Honestly, I was shocked that [Portland] did that," said Russillo.
"It's starting to look worse now that we've seen some of the free agent money -- Jrue's going to make that with some of the prices that guys got. I might have been wrong on that one," Simmons added.
Free agency makes Blazers' Jrue Holiday trade even more questionable
Russillo credits the Celtics' ability to find a landing spot for Holiday, getting out of his three-year, $104 million contract without attaching any draft picks. Initially, the Blazers were the ones who somehow sent the draft capital over to Boston. The previously reported deal had Portland including two future second-round picks. That has officially been revised as the full details of the trade have been finalized.
The trade is now a one-for-one swap of Holiday and Anfernee Simons, as Aaron Fentress of The Oregonian reports that the Blazers had slight concerns surrounding Holiday's medicals (although they weren't significant enough to call off the deal entirely).
The financial and injury concerns surrounding Holiday make this an unnecessary risk for the Blazers. The salary cap is set to increase by ten percent; however, it's still hard to justify paying Holiday an average of $33.7 million annually after seeing the free agency signings.
Here are a few role players who didn't receive massive contracts in free agency:
- Dorian Finney-Smith agreed to a four-year, $53 million deal with the Houston Rockets
- D'Angelo Russell agreed to a two-year, $13 million deal with the Dallas Mavericks
- Ty Jerome agreed to a three-year, $28 million deal with the Memphis Grizzlies
- Clint Capela agreed to a three-year, $21.5 million deal with the Houston Rockets
- Brook Lopez agreed to a two-year, $18 million deal with the Los Angeles Clippers
While Holiday is more impactful than these players, he's still not going to be the needle-mover that the Blazers desperately need, especially at 35 and coming off a down season in Boston.
Trading away Simons' expiring deal wasn't the biggest question in the trade; it was whether it was worth taking on Holiday's contract. Teams must be highly selective with the deals they take on under the new CBA, reflecting these free agency prices.
Between Holiday and Jerami Grant, the Blazers have two of the worst contracts in the entire league. That's not an ideal position to be in for a team that has simply making the playoffs as their ultimate goal for next season; it's the exact type of thing that gets teams stuck in purgatory.