2023-24 season: 21-61

Highlight of the season: A six-game stretch in mid-March when Deandre Ayton averaged 26.8 points and 15 rebounds and looked like the player they thought they were getting last offseason.

How it ended

Pretty much as expected. The franchise made a conscious effort to pivot toward something new, trading former All-NBA guard Damian Lillard to the Milwaukee Bucks, thus empowering third-overall selection Scoot Henderson to take over the most difficult job in the NBA at the age of 19, while inexplicably hanging on to multiple veterans, who weren’t flipped at February's trade deadline.

Not helping matters for Portland’s backcourt was the fact that second-year guard Shaedon Sharpe played just 32 games, veteran guard Malcolm Brogdon 39 and high-scoring guard Anfernee Simons 46. Injuries also hit the Blazers' frontcourt rotation with Robert Williams going out after just six games, the aforementioned Ayton playing in just 55 games, and Jerami Grant playing 54 games.

Injuries aside, the Blazers weren’t going anywhere interesting even if healthy, nor should they have tried to. This season should have been a showreel for Brogdon, Williams and Grant in particular, with the idea of pumping up their trade values and moving away from them at the deadline for young players or draft-pick compensation. That goal can still be achieved this summer, for Grant at least, but major questions hover over the oft-injured pair of Brogdon and Williams, with teams likely to demand significant discounts in taking on those contracts.

As for Portland’s biggest story this year, that being the play of Henderson, reviews were not exactly flattering. The rookie averaged a modest 14 points and 5.4 assists on the year, finishing just 50.3% of his shots near the rim, which is a low, low number for a guy who was billed as a Derrick Rose/John Wall combo. Henderson did get better as the season progressed and found some much-needed success in the mid-range area that’s likely to carry over to next season. But as the Blazers probably presumed they’d found their star player for the next decade, expectations likely have been tempered on that front.

There is a good story coming out of Portland, though. Duop Reath, an undrafted 27-year-old who attended LSU in 2018, made the roster and carved out a niche role for himself as a floor-spacing big man. Reath appeared in 68 games and averaged over nine points per game on effective shooting, making him an attractive trade piece this summer for teams that are looking for cheap bench upgrades. Reath, who will earn around $2 million next season, fits that bill, and the Blazers can justify asking for significant compensation.

As the Blazers move forward, they must not waste time by hanging on to expensive veteran contracts. Grant, 30, shouldn’t have a role on this team long term, as it's trying to develop Henderson and Sharpe, both projected to be high-volume shot-takers for the franchise for years. Getting him and Brogdon out of town, in return for younger pieces, has to be the priority.

Biggest offseason need

With no player coming close to 2,000 minutes played this season, a new medical team would be a start. If that isn’t in the cards, the team could stand to use a high-level wing who can grow with the core of Henderson, Sharpe and potentially Ayton. The Blazers have a high pick in this year’s draft and need to continue to find quality assets with upside.

Draft focus

Portland has two lottery picks and an early second rounder, so there's a lot to work with. Henderson started to figure things out toward the end of the season, and the backcourt is set with Simons and Sharpe. It opens things up to target an inside-out player, like G League Ignite forward Matas Buzelis, or add a bigger body to go against the size in the West, like UConn's Donovan Clingan, Purdue's Zach Edey or Ulrich Chomche, a 6-11 forward from the NBA Academy Africa. — Krysten Peek.

Draft picks: Nos. 7, 14, 33 and 40

Salary cap breakdown

The salary cap is likely to check in at $141 million, and the Blazers currently have $145 million locked up in their seven most expensive players. Long story short, they will not have cap space, which further underlines the need of getting out of Grant’s deal, which has four years left on it, and Williams', which has another two years left on it.

The Blazers might believe they have time to sort all this, and they could be right. But for a rebuilding team that is sorely in need of assets, not being able to rent out cap space is a massive competitive disadvantage. General manager Joe Cronin might have to excuse himself from a lot of summer parties this year, as his phone should be fully attached to his hand at all times.

Key free agents: None.

Next season’s goal

The Blazers are in sore need of some roster symmetry and some constructed hierarchy. Half the players don’t know if they’re staying or going, and the players that do have an inkling of their long-term place have yet to carve out their roles for the future. Building a roster that helps each understand his spot on the team will be crucial, and that means lessening the guard glut and presenting a team with more obvious roles that will come more naturally to each party. Finally, while winning shouldn’t be the main driver for next season, they will need to find a way to experience more success. Young players stuck in a web of constant losses, while not knowing what’s next, rarely tend to develop at the rate needed.

What can move the fantasy needle

Simons stressed the need to win in his exit interview. However, that's a challenge without chemistry in the starting unit. The Blazers had 41 different starting lineups this season, ranking second in the league behind the Memphis Grizzlies. Continuity is critical to turning around a franchise searching for a post-Damian Lillard identity. It doesn't help that their financial situation is in shambles, so I'd expect them to move some vets — which would be great news for players like Henderson, Reath, Jabari Walker and Kris Murray. — Dan Titus