Jrue Holiday hasn't played since November 14th, when he suffered a right calf strain in the Portland Trail Blazers' blowout loss to the Houston Rockets. The veteran guard was initially given a reevaluation timeline of one to two weeks. Since then, the Blazers have lost seven of their last nine games, falling to tenth in the Western Conference standings with an 8-13 record.
This recent stretch has shown how vital Holiday's playmaking and veteran presence are for a young Blazers team. At the same time, it's also exposed flaws in the Blazers' approach to acquiring an aging, somewhat injury-prone star in the first place.
There were supposed to be both short and long-term benefits from swapping Anfernee Simons for Holiday with the Boston Celtics this summer. In many ways, Holiday was going to be what Fred VanVleet was to an up-and-coming Houston Rockets roster, serving as a bridge to help them return to the postseason while the young core continues to develop. However, as this latest losing streak has shown, Portland's young core is nowhere near what was brewing in Houston.
Blazers risk purgatory with Jrue Holiday trade
At 35 years old, Holiday is only getting older and more expensive. The Blazers owe him $32.4 million this season, and $34.8 million next year, with a $37.2 million player option in 2027-28 he'll almost certainly pick up. That's a lot to invest in a player who has averaged 64.2 games played over the last six seasons (he wouldn't even be eligible for end-of-season awards!)
As his stints in Milwaukee and Boston have shown, Holiday is a great two-way guard and the ideal piece to put a contending team over the top. But in Portland's case, given their rebuilding timeline and his contract, this is an unnecessary risk to take on, both in terms of availability and the potential for a decline in play due to his age and these injuries.
The Blazers are a better team than this recent stretch has indicated and should be able to right the ship when their roster gets healthier and the schedule lightens up. But what does righting the ship even look like for this season? Making the play-in tournament?
The Blazers were expected to be in the Cooper Flagg sweepstakes last season, yet finished with 36 wins and ended up with a project in rookie Yang Hansen. The strong 2026 draft class also presents a golden opportunity for them to finally land that missing star via the draft, yet the Blazers are trending towards another late lottery pick, in large part because of the Holiday trade.
If this recent stretch played out over the entire season, that would be great for their draft lottery odds. If their strong start to the season were maintained for 82 games, that would be great for their playoff chances. But neither is reality with Holiday on the roster -- not at this point in his career.
Portland is now in no man's land, struggling to straddle these two timelines as a team that made a win-now move while maintaining a long-term mindset.