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The Portland Trail Blazers entered the 2025 offseason coming off a brutal 2024-25 campaign, finishing with just 36 wins and sitting near the bottom of the Western Conference standings. The season saw extended absences for young cornerstone Scoot Henderson, inconsistency from Shaedon Sharpe, and a lack of veteran leadership following the post-Lillard era.
For a franchise that spent over a decade with a defined identity under Damian Lillard, the Blazers looked like a team wandering in search of itself. Changes were inevitable, and it came fast. What followed was one of the most unexpected offseasons in franchise history. The Trail Blazers didn’t chase stars or cap out their flexibility. Instead, they brought back a franchise icon, added proven defense-first veterans, and retained a promising young core. This is how you rebuild with dignity — not by tanking recklessly, but by setting a high cultural floor and developing with purpose. Below is the breakdown of every free agency signing with grades and notable trades.
The return of the king: Damian Lillard signs with Blazers
Back where it started ⌚️ pic.twitter.com/bqtmFjr9Lm
— Portland Trail Blazers (@trailblazers) July 19, 2025
In a surprising and emotional turn of events, Damian Lillard returns to Portland just one year after being traded to Milwaukee. Signing a three-year deal worth $42 million, Lillard’s return wasn’t just a nostalgic move — it was strategic.
After a short and ultimately unfulfilling stint with the Bucks, Lillard chose to return to a city and franchise that still viewed him as its spiritual leader. From Portland’s perspective, bringing Lillard back accomplishes several things: On the court, Lillard might no longer be in his MVP prime, but he can still average 22-25 points per game with elite shot creation. Off the court, his impact on team culture and the locker room can’t be overstated.
While the move might hinder long-term development minutes for younger guards, Lillard’s presence ensures the Blazers don’t spiral into irrelevance. For a team still reeling from losing its identity, this is a huge win.
Grade: A
Rayan Rupert re-signs on a team-friendly deal
Composed. Controlled. Clutch. pic.twitter.com/PA8ZsHfiXV
— Portland Trail Blazers (@trailblazers) July 16, 2025
A less flashy but very smart move was re-signing Rayan Rupert to a 3-year, $24 million extension. The 6-foot-7 French wing showed flashes of elite defensive instincts and three-point shooting toward the end of the season. At just 21 years old, he profiles as a potential 3-and-D specialist who could one day be a full-time starter.
The deal is low-risk, high-reward. Even if Rupert tops out as a rotation wing, the contract is more than fair value. If he blossoms into a 10-point-per-game 3&D specialist, it’s a steal.
Given how Portland’s recent draft picks have fared, locking in a young, improving talent like Rupert without overpaying shows smarter cap management than in past years.
Grade: B
Matisse Thybulle re-signs
Thybulle, a restricted free agent, opted into his player option to stay in Portland. While his offensive limitations remain glaring, he’s still one of the best perimeter defenders in the league. For a team investing in young scorers, having a defensive specialist like Thybulle balances the equation.
The short-term nature of the contract means flexibility — Portland can easily move on if better options emerge. But Thybulle can still start in certain matchups and provide elite wing defense, especially when paired with Jrue Holiday.
Grade: B-
Defensive backbone: Jrue Holiday acquired via trade
10 toes to the ground. pic.twitter.com/IPxcCBDZnV
— Portland Trail Blazers (@trailblazers) July 7, 2025
The other seismic move was trading for Jrue Holiday, who was acquired from the Boston Celtics. At 35, Holiday is still one of the best defensive guards in the NBA. Pairing him with Lillard recreates one of the most balanced backcourts in the league, albeit with an older timeline. This move signals that Portland isn’t tanking — they’re aiming to compete now, at least as a scrappy play-in contender.
Holiday also gives head coach Chauncey Billups a reliable two-way presence that can help stabilize young wings like Sharpe and Rupert.
The only knock? This could cost development minutes for Henderson, unless the Blazers go three-guard heavy. Still, the deal shows a real commitment to turning the page on their bottom-tier status and returning to professionalism and effort on both ends.
Youth, veteran balance, and the Blazers' new direction
This 2025 offseason marked a philosophical shift for the Blazers. Rather than going all-in on a youth rebuild, the front office chose a hybrid path: one that blends veteran leadership with development.
The return of Lillard and the acquisition of Holiday provide a sense of direction and urgency, while younger players like Scoot Henderson, Shaedon Sharpe, Rayan Rupert, Kris Murray, and Duop Reath are still being groomed.
It’s not a championship roster — and it probably won’t even be a playoff team — but for the first time since Lillard’s departure, Portland looks like a franchise with a clear ethos: compete hard, defend consistently, and develop from within.
The Trail Blazers are still going to give their young guys plenty of time to make mistakes, but this is a year in which they want to see some progress. They're going to start making decisions on who they want to build around.
