36 years old and all, I would definitely consider Jrue Holiday to still be a coveted asset on any NBA roster.
He is arguably one of the most underrated guards in league history, with his combination of lockdown defense, elite playmaking, and quality scoring to complement it all. Holiday was already a wily guard back in his youth, but he only got better with age as he was a core pillar in two eventual championship triumphs — the Milwaukee Bucks in 2021 and the Boston Celtics in 2024.
Now, Holiday finds himself as a veteran leader for the Portland Trail Blazers. The Blazers boast several key youngsters like Deni Avdija, Shaedon Sharpe, Toumani Camara, Donovan Clingan, and Scoot Henderson. However, Portland made a stunning summer splash to acquire Ja Morant through trade, while they also await a healthy Damian Lillard to make a spirited comeback to Rip City.
With the clear guard logjam, the status of Jrue Holiday on this team moving forward was something that began to become a talking point amongst basketball circles. In fact, right after the Ja Morant deal went down, I got right on the jump of raising the idea for Toronto to go all-in on Jrue Holiday. The idea of adding Holiday certainly looked more alluring after the Raptors got inserted in this Kawhi Leonard trade hoopla, a deal which is still in the midst of being finalized, but should all things go to the Raps' plans — they will definitely be a team to watch next year.
The real question or questions regarding a Raptors–Jrue Holiday link was how they could realistically get there? Holiday's current salary is roughly $35 million with a near $38 million player option on the horizon next offseason, which is certainly a high price to pay for an old-timer, but Toronto does have the money on their books to try and get there. Although, there was perhaps a slim chance circulating that Holiday could be a buyout candidate, which would absolutely be the more ideal path for the Raptors to throw their name in the hat.
Unfortunately, a recent update on that idea from NBA insider Marc Stein dampens any hopes of it becoming a possibility.
A Jrue Holiday buyout that would make him easily available to the Raptors is unlikely
Stein writes in a late-night intel piece for his Substack on August 3 (subscription-required link here): "[...] recent speculation about a Jrue Holiday buyout from the Trail Blazers is erroneous. It has become a popular online pastime to suggest that such an arrangement is percolating that helps route Holiday back to the team that drafted him — which obviously fancies itself as a Superteam now after the Sixers acquired Brown and James — but league sources say Portland is not about to just usher Holiday onto the open market. The Blazers have been messaging for some time that they would like to keep Holiday … even after trading for Ja Morant and with Damian Lillard poised to make a comeback after losing a full season to an Achilles tear."
As a Raptors fan, I naturally wish for a seasoned veteran like Holiday to be playing in Toronto — arguably their best pure point guard since Kyle Lowry. But at the same time, I completely understand Portland's reasoning. The Blazers aren't some rebuilding team looking to thin out; despite the tough Western Conference, they're aiming to be a sleeper team to watch (just like the Raps are trying to be out East).
Having a player of Holiday's caliber on the roster is a luxury they wouldn't want to relinquish easily. That being said, I would still keep an eye on Holiday as a potential trade candidate as the season unfolds, as we could see entirely new developments emerge by the trade deadline.
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