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.