Jrue Holiday started his Portland Trail Blazers tenure on an incredibly strong note. He appeared to be an ideal fit for this young roster, providing valuable mentorship and underrated playmaking, among several other things that translate to winning basketball.
Unfortunately, that honeymoon phase ended on Nov. 14, when Holiday suffered a calf strain. That injury has lingered into 2026 as Holiday remains without a timeline to return.
It's the combination of Holiday's age, contract, and injury history that makes analysts like Bobby Krivitsky of Hardwood Houdini wonder if trading for Holiday was truly in Portland's best interest.
"Even so, seeing Holiday, at 34, play with heavy legs and watching his production dip may have signaled to the Celtics that, as much as they love the person and the player, it was in their best interest to trade him," Krivitsky writes.
Blazers' Jrue Holiday trade could backfire
It was expected that Portland would trade Anfernee Simons to proactively get ahead of his expiring contract. That's a problem that the Celtics currently face with Simons, who remains a trade candidate leading up to the Feb. 5 deadline. Still, that is not as concerning as the Holiday situation Portland is currently dealing with.
He's already 35 years old and is on the books until the 2027-28 season, where he has a massive $37.2 million player option. As Krivitsky notes, that leaves many Blazers fans worried about how this contract will age.
"Naturally, the organization and Portland's fan base may worry about how the potential future Hall of Famer will age over the rest of his contract. He's on the books for $34.8 million for the 2026-27 season. Holiday has a player option worth $37.2 million for the following year."
Of course, there were benefits to bringing in Holiday. He makes much more of a two-way impact than Simons, even when factoring in his declining athleticism. The fact that Holiday was able to bounce back from his underwhelming Celtics season, in which he averaged just 11.1 points and 3.9 assists, is a promising sign that he still has gas left in the tank.
It's also challenging to put a number on the actual value he provides when factoring in what he brings to the table both on and off the court for a Blazers team that desperately needed his veteran leadership after head coach Chauncey Billups' messy situation.
Still, all things considered, there was a lot of unnecessary risk associated with bringing in Holiday. His recent injury has exposed some of those risks, and it should have Blazers fans concerned about how the remainder of his career plays out on an already overpaid salary.
"Still, with 16 years of mileage on his tires, even while loving what he brings to the locker room, at 35, the concerns about what's to come for his playing career won't subside."