The Portland Trail Blazers shocked much of the league on Monday night when they traded Anfernee Simons to the Boston Celtics in exchange for veteran guard Jrue Holiday. What initially looked like a salary-dump for Boston quickly turned into a move that could reshape Portland’s future — and fast.
While the Celtics clear cap space and add a rising scorer in Simons, the Blazers quietly may have walked away with something even more valuable: direction.
Portland has missed the playoffs four years in a row, failed to eclipse 37 wins in any of those seasons, and struggled to stay relevant in an increasingly competitive Western Conference. But this trade signals a shift — one that blends veteran leadership with a promising young core.
Enter: Jrue Holiday
Adding Holiday isn’t just a move for locker room presence — it’s a full-scale investment in winning now. The two-time NBA champion brings defensive intensity, playoff experience, and a no-nonsense approach that Portland sorely lacked.
Yes, he’s 36. Yes, his contract is steep. But what he offers — on the floor and behind the scenes — could set the tone for a young team trying to turn a corner.
More importantly, the trade shifts the spotlight back onto Portland’s front office, which suddenly appears more aggressive, intentional, and ready to retool on the fly. Re-signing head coach Chauncey Billups in April laid a foundation. The Holiday trade begins to build on it. And the moves might not be done yet.
Jerami Grant & Deandre Ayton: What comes next?
Two of Portland’s most seasoned veterans — Jerami Grant and Deandre Ayton — are now firmly on the radar as trade chips.
Jerami Grant:
Grant has been a solid contributor since arriving in Portland, averaging 18.9 points on 44 percent shooting from the field and nearly 39 percent from deep over the last three seasons. But he’s struggled to stay healthy, appearing in just 101 of 164 games over the past two years. Set to make $32 million next season, his value is complicated by both injury history and age.
Still, the presence of Holiday could serve as motivation for Grant to stay sharp and engaged. If he’s healthy, he’s a plus starter. If not, Portland may explore flipping him to a contender in need of veteran scoring on the wing.
Deandre Ayton:
Ayton’s situation feels more tenuous. The 26-year-old center has failed to meet expectations since joining the Blazers, posting 14.0 points and 10.2 rebounds last season. Like Grant, injuries have kept him off the court — just 95 of 164 games played since his arrival.
With a $35 million price tag next year and unrestricted free agency looming in 2026, Ayton is the likeliest of the two to be moved. Especially with the emergence of rookie Donovan Clingan, who has already flashed advanced defensive instincts and positional awareness — and, more importantly, is on a team-friendly rookie deal through 2028.
Clingan doesn’t just represent the future — he might already be the better option.
The playoffs are the Goal — and it’s within reach
This isn’t about a deep playoff run. Not yet.
For a franchise that’s spent four straight years on the outside looking in, just getting to the play-in tournament would be a win. It gives fans a taste of competitiveness. It gives the roster real stakes. And it gives the front office a reason to keep building.
Whether the final version of this team features Holiday, Grant, Ayton, or a few new names, the Trail Blazers are doing something they haven’t done in years:
Trying to win.
And if they keep pushing the right buttons, they might not be a punchline anymore. In fact, they might just be a sleeper out West.