The Portland Trail Blazers had a vision for their team this season. An elite defense paired with enough offense to make the playoffs in a competitive Western Conference. Unfortunately, as their season unravels around them, their moves this summer look like a collection of grave mistakes.
In 2020, the Milwaukee Bucks traded for Jrue Holiday, a move that proved to be the finishing touch they needed for a championship roster. They promptly went all the way to the NBA Finals and won the title, with Holiday playing a key role as the starting point guard.
In 2023, the Boston Celtics traded for Jrue Holiday, a move that proved to be the finishing touch they needed for their championship roster. They proceeded to mow through the Eastern Conference en route to the NBA Finals and a championship, with Holiday's two-way play a key part of their dominance.
In 2025, the Portland Trail Blazers somehow convinced themselves that what they needed was to trade for Holiday. He is an incredible human being and veteran player who can absolutely still help a team win. He is also 35 years old and making $104 million over this season and the next two. He should have had negative trade value given his age and contract, but the Blazers decided to pursue him at positive value.
Squint, and you understand the vision. Holiday would be a defensive dynamo in the backcourt and pair well either alongside Scoot Henderson or in place of him. A lineup including Donovan Clingan, Deni Avdija and All-Defense forward Toumani Camara alongside Jrue Holiday may be so good defensively that the offense almost didn't matter.
Trading for Jrue Holiday was a mistake
Unfortunately for the Blazers, things have not worked out as they envisioned. Rather than being a surprise playoff team, they sit at just 12-18, in 10th place and likely to slip down even further as the teams behind them put out their own fires. Their offense is unsurprisingly 22nd in the league, but their defense is shockingly just 22nd in the league. They have been a disaster on that end.
Part of that is that Holiday has been limited to just 12 games due to multiple injuries. He remains out currently due to a calf injury that has him listed day to day. Yet that is also another indictment of their win-now moves: they took on the salary of Holiday despite his age and injury history.
This clearly was not a group ready to win now, despite uncovering Camara and overseeing Avdija's leap into stardom. Viewing Holiday as the win-now move they needed to push up the ladder was incorrect, as they were not in a position to do that, but even in the best-case scenario, they were not a contender. Holiday is a finishing touch, not a midstream luxury.
The Trail Blazers have multiple players with upside to grow into more, and they have found keepers across the frontcourt line. Yet to take the next step they need patience, patience they did not display this summer. And given how much Holiday makes over the next few seasons, their impatience could prove to be a grave mistake that stunts their growth rather than accelerates it.
Portland's front office may deserve coal this Christmas.