For the better part of the last half-decade, the Portland Trail Blazers have been mired in mediocrity, unable to reclaim the magic that once made them a perennial playoff presence in the Western Conference. Four consecutive seasons without a playoff berth created tension within the fan base and doubt across the league about whether the franchise could ever build a competitive roster again. Yet, after last year’s encouraging step forward — 36 wins, a renewed identity, and a clear commitment to their youth — Portland appears ready to declare itself a team on the rise once more.

General manager Joe Cronin set the tone for the offseason by stating that it’s “winning time” for the Blazers, and the team’s moves reflected that vision. Damian Lillard is back in a Blazers uniform, joined by Jrue Holiday and promising rookie Yang Hansen, while young stars Scoot Henderson and Shaedon Sharpe continue to develop. This roster is no longer an experimental project of mismatched parts. It’s one with the balance of experience and youth necessary to claw its way back into the Western Conference playoff race. The question is whether all of that will be enough in a brutal conference loaded with contenders.

Learning from last year’s struggles

The 2024-25 campaign ended with the Blazers finishing 36-46, a record that placed them just outside the play-in tournament. While disappointing, it marked progress compared to prior seasons and suggested that Chauncey Billups had finally found a measure of consistency with a team that was beginning to buy into his vision. Henderson and Sharpe showed flashes of becoming one of the most dynamic backcourts of the future.

Still, the roster’s flaws were glaring. The Blazers ranked near the bottom of the league in defensive efficiency, struggled to close out tight games, and often looked overmatched against more experienced squads. Depth was another concern, particularly in the frontcourt, where injuries to Robert Williams III left Portland exposed. While the season ended without postseason basketball, the trajectory was upward; a stark contrast to the freefall of prior years.

The impact of Damian Lillard and Jrue Holiday

The biggest storyline entering 2025-26 is the return of Lillard. His reunion with Portland was as shocking as his departure in the first place, but it signals one thing above all: the Blazers intend to win now. Lillard’s leadership and offensive brilliance are unquestioned, and even if his best years are behind him, his presence will transform the locker room. Pairing him with Jrue Holiday gives the Blazers one of the most seasoned and defensively sound backcourts in the league, providing a veteran foundation to balance the explosive but still-developing games of Henderson and Sharpe.

This mix of generations may be exactly what Portland needs. Lillard and Holiday bring playoff experience, late-game poise, and defensive stability, while Henderson and Sharpe bring athleticism, speed, and upside. How Billups manages the rotations will be crucial, but the blend of youth and veterans should allow Portland to avoid the inconsistency that doomed them last year.

Schedule outlook and win predictions

The 2025-26 NBA schedule presents Portland with both opportunities and challenges. They open with a favorable slate, including winnable games against Minnesota, Utah, and Detroit, but face gauntlets in December and January with back-to-back series against Golden State, Los Angeles, and Denver. For a team seeking to build confidence and establish rhythm, those stretches will be defining.

Last season’s 36 wins serve as the baseline, and it’s fair to project improvement with the roster additions and the natural growth of Henderson and Sharpe. A realistic prediction would be between 40 and 44 wins, with the midpoint projection landing at a record of 42-40. That kind of record should slot Portland somewhere between the 8th and 10th seeds in the Western Conference, making them a play-in contender and giving Rip City its first taste of postseason basketball in years.

Playoff outlook for Trail Blazers

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If Portland reaches the play-in tournament, its chances of advancing into the official playoff bracket depend on health and matchups. A play-in game against seasoned squads like the Lakers, Mavericks, or Kings would be a steep challenge, but the Blazers’ veteran additions give them a puncher’s chance. Realistically, Portland’s ceiling this year is a first-round playoff exit, but the experience would be invaluable for Henderson and Sharpe, who are being groomed to lead the franchise into the next decade.

Predictions beyond the record

Beyond the win-loss column, several predictions can be made about Portland’s season. Scoot Henderson, entering his second full season as the starting point guard, could emerge as a Most Improved Player candidate if he maintains consistency and cuts down on turnovers. Shaedon Sharpe’s athleticism and scoring could also push him into Sixth Man of the Year conversations, particularly if Billups opts to bring him off the bench behind Lillard and Holiday.

On the coaching front, Chauncey Billups enters the year with pressure. The franchise has been patient with his development as a head coach, but with a more complete roster, the excuses for underperforming are dwindling. If Portland starts slow or looks unprepared against top-tier competition, the front office could consider making a change. While a midseason firing is unlikely, Billups’ seat will grow warm if the Blazers underachieve.

As for trades, Jerami Grant remains the likeliest piece to move. If the Blazers are in contention, they may keep him for stability. But if the season trends downward, expect contenders to come calling with offers, forcing Portland to decide between chasing short-term success and planning for long-term growth.

A step forward, but not the finish line

The Portland Trail Blazers enter the 2025-26 season with cautious optimism. They’ve added veterans who bring stability, retained their promising young core, and embraced the idea that they’re done rebuilding. After years of irrelevance, Rip City basketball finally has direction again.

Still, this season isn’t about championship contention; it’s about taking the next step forward. A 42-40 record and a spot in the play-in tournament would be a success, even if it ends in a first-round playoff exit. For a franchise starved of postseason basketball, progress matters.

In the long run, the development of Henderson and Sharpe, the handling of Grant and Williams, and the eventual transition from Lillard’s leadership to a new generation will define Portland’s future. But for now, the Blazers have their eyes set on one simple goal: returning to the playoffs and proving that Rip City basketball still belongs in the Western Conference conversation.