Blazers' Jrue Holiday worries just got worse after full trade details finalized

Apr 20, 2025; Boston, Massachusetts, USA; Boston Celtics guard Jrue Holiday (4) reacts after a play during the second 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) reacts after a play during the second against the Orlando Magic at TD Garden. Mandatory Credit: Bob DeChiara-Imagn Images | Bob DeChiara-Imagn Images

The Portland Trail Blazers' trade for Jrue Holiday was initially reported to be sending over Anfernee Simons and two future second-round picks. However, this became a one-for-one swap with no draft capital attached because of Holiday's medicals.

A source told Aaron Fentress of The Oregonian that the review of Holiday's medicals wasn't "substantial enough to warrant the trade being negated," but that it was enough to alter the terms of the deal.

Initially, you'd assume that this revised trade is a win for the Blazers -- they landed the player they wanted all along and at a cheaper value than they were previously willing to commit to. But evaluating it further, it's actually a negative update for the Blazers.

Blazers' Jrue Holiday trade is an unnecessary risk

The draft capital was a sweetener rather than the focal point of the deal. The most significant question in Portland making this trade is whether Holiday justifies his three-year, $104 million contract.

As Fentress notes, Portland's rebuilding timeline doesn't align with the 35-year-old guard, meaning they could try to flip Holiday to a contender at the deadline. But this trade is a significant and unnecessary risk for Portland to take on when they could have just flipped Simons at the deadline last season instead.

Holiday has averaged 63.2 games played in the past five seasons, and his stats have rapidly declined over the past two years in Boston. Last season with the Celtics, Holiday averaged 11.1 points, 3.9 assists, 4.3 rebounds, and 1.1 steals per game on 44/35/91 shooting splits. Part of that was due to his decreased role on a championship roster, so those numbers may improve in Portland. However, the eye test also suggested that Holiday's age and injuries were responsible for the declining production.

The fact that something in Holiday's medicals is worth revising the trade over shouldn't be overlooked, especially given the steep amount Portland has invested in him financially. If Holiday's injuries hamper his play and availability, finding someone willing to take him on at the deadline will be much more challenging. They'd have a Jerami Grant situation all over again -- a veteran who doesn't fit their timeline and is overpaid on a long-term contract.

The Blazers were well-positioned to clear cap space with Anfernee Simons expiring deal. Instead, they took on an expensive mentor for Scoot Henderson in a win-now move to end a four-year playoff drought. They never should've taken on this risk, given the massive disparity between where they are in their rebuilding timeline and where Holiday is in his career.

And the fact that he's not fully healthy coming over when the deal was already a win for Boston in the first place makes it all the more lopsided.