Portland’s Jrue Holiday Gamble Backfires as Blazers Struggle to Find Their Identity
The Portland Trail Blazers entered this season with a clear vision: build a defense-first identity strong enough to compete in the loaded Western Conference, while letting the offense develop around young talent. But nearly halfway through the season, that plan has unraveled-and fast. What was supposed to be a bold step forward now looks more like a misstep that could set the franchise back.
At the heart of that gamble? A blockbuster trade for veteran guard Jrue Holiday.
On paper, it had echoes of past success stories. In 2020, Holiday was the final piece that helped the Milwaukee Bucks capture a title.
In 2023, the Boston Celtics made a similar move, adding Holiday as the finishing touch to a championship roster. In both cases, he brought elite perimeter defense, veteran leadership, and the kind of poise that elevates contenders.
But Portland isn’t Milwaukee in 2020. And they’re not Boston in 2023.
The Blazers aren’t a piece away-they’re a team still trying to figure out who they are. That’s what makes the decision to acquire Holiday, now 35 and owed $104 million over the next three seasons, so puzzling.
He’s still a high-impact player when healthy, but at this stage in his career, he’s not someone you build around-he’s someone you add when you’re ready to win now.
The Blazers, clearly, are not.
The vision made some sense in theory. Holiday anchoring the backcourt defensively, flanked by rising talents like Donovan Clingan, Deni Avdija, and Toumani Camara, could’ve made Portland a defensive nightmare. Add in Scoot Henderson’s development and maybe-just maybe-they’d have enough on offense to sneak into the playoff picture.
But visions don’t win games. Execution does. And so far, the Blazers have struggled on both ends of the floor.
They’re sitting at 12-18, clinging to 10th place in the West, and trending in the wrong direction. Their offense ranks 22nd in the league, which isn’t shocking given their youth and lack of offensive firepower.
But the real disappointment has been the defense-also 22nd in the NBA. That’s the part that was supposed to keep them afloat.
Instead, it’s been a liability.
Holiday’s limited availability hasn’t helped. He’s played in just 12 games due to a string of injuries, the latest being a calf issue that has him listed day-to-day.
And while injuries are part of the game, Portland’s front office knew what they were signing up for. Holiday’s age and mileage were no secret, and committing long-term money to a player with his wear-and-tear was always going to be a risk.
The bigger issue is philosophical. This wasn’t a team ready to make a win-now move.
Yes, they’ve uncovered some promising pieces-Camara looks like a defensive gem, and Avdija has taken a noticeable leap. But the core is still young, still raw, and still learning how to win in the NBA.
Holiday isn’t the guy to lead a rebuild-he’s the guy you bring in after the rebuild is done.
That’s where the disconnect lies. Portland treated Holiday like a shortcut to contention, when in reality, they needed to stay the course.
Instead of letting their young roster grow together and build chemistry, they tried to accelerate the timeline. And now, with Holiday’s massive contract on the books and no clear path to playoff relevance, they’re stuck in a tough spot.
None of this is a knock on Holiday himself. He’s a consummate pro, a proven winner, and one of the league’s most respected veterans.
But timing matters in the NBA. And this move-however well-intentioned-was mistimed.
The Blazers aren’t without hope. They’ve got intriguing talent across the frontcourt, and Scoot Henderson still has the tools to be a franchise cornerstone.
But to unlock that potential, they’ll need patience-something that was in short supply this past offseason. Instead of nurturing their young core, they made a move designed for a team that was already close to the finish line.
Now, they’re left trying to recalibrate on the fly. And with Holiday’s contract looming large over the next two seasons, that recalibration won’t come easy.
Portland’s future still holds promise. But this season’s detour might end up costing them more than just a few wins-it may have delayed the very progress they were so eager to accelerate.