The Portland Trail Blazers have put themselves right in the middle of the league’s most interesting conversation heading into the 2026-27 season.
After a surprise run to the playoffs last year as the No. 7 seed, Portland spent the summer going for more. The headline move was adding Ja Morant, and the Blazers also get a healthy Damian Lillard back in the mix. That gives them a guard group that suddenly looks crowded, with Jrue Holiday and Scoot Henderson also in the picture, but it’s the kind of problem teams usually dream about having.
What makes Portland so intriguing is that it didn’t settle after last season’s quick exit against the San Antonio Spurs. The Blazers had a plan, and they followed through on it. They took a swing on Morant as a buy-low star, betting that a change of scenery could help unlock something closer to his best version again.
That’s the gamble. Morant has been trending down over the last four seasons, and he’s nowhere near the All-NBA level he reached in 2021-22.
Still, Portland didn’t pay a steep price to get him, which keeps the move from looking reckless. If he climbs back toward that old level, he could wind up looking like a steal.
The same logic applies to Lillard. If he can give the Blazers 80% of the player he was with the Milwaukee Bucks, that would be tremendous value for what Portland is paying him.
If the pieces fit, the Blazers’ likely starting group would feature Morant and Lillard together, alongside Holiday, Deni Avdija, and Donovan Clingan. That’s a lineup with enough talent to make Portland a real dark horse in the playoff race.
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Sidy Cissoko is suddenly part of that conversation, alongside Vit Krejci, as the Blazers look for bodies who can handle real rotation work. Portland also brought in Jeremy Sochan on a non-guaranteed deal, so there is still competition for those minutes, but the door has opened wide enough for Cissoko to make a case for himself if the opportunity holds. [Read more 🡒]
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What makes the conversation linger, though, is how much it echoes the road Portland kept choosing at the time. McCollum was eventually dealt to New Orleans in the 2021-22 season as the Blazers doubled down on Damian Lillard, only for Lillard to later be gone after the 2022-23 season. McCollums contract story is another reminder of how close the team came to a different version of its core, and how many of those old decisions still hang over the franchise. [Read more 🡒]
Shaedon Sharpe Suddenly Feels Caught In Portlands Biggest Roster Squeeze
The Blazers backcourt is starting to look like a crowded, complicated puzzle, and Shaedon Sharpe is suddenly one of the pieces that does not fit as cleanly as it once seemed. Portland still has not made a call on Scoot Hendersons rookie-scale extension situation before the 2026-27 season, and the front office is trying to sort out a roster that needs more shooting and defense while also figuring out which young guards are truly part of the long-term core.
Sharpes place in that mix is especially murky because of how his season has unfolded and what his injury timetable could mean for the teams plans. If he is not back until late winter, the Blazers may have to weigh a February trade deadline decision without seeing much of him in game action, and his role has already been uncertain after falling out of the rotation under two head coaches. For a team trying to balance development with upgrades, that leaves Sharpe in the middle of one of Portlands most pressing roster questions. [Read more 🡒]