Five questions Trail Blazers face after returning to playoffs

A season that started with the chaos of head coach Chauncey Billups' arrest ended with the Portland Trail Blazers' first trip to the playoffs in five seasons. With a new owner, a returning superstar and an unsigned head coach, the Blazers have a lot of big decisions this summer.

Here are five questions the Blazers must answer to continue their rise in the Western Conference.

1. What does Damian Lillard have left after his Achilles injury?

The Blazers brought back Damian Lillard on a two-year deal after he tore his Achilles in the 2025 playoffs and the Milwaukee Bucks bought out his contract. Lillard spent the 2025-26 season rehabbing his injury, taking the court only to deliver a surprising win at the Three-Point Contest on All-Star Weekend.

Lillard proved he is still elite at shooting three-pointers off a rack, but it's hard to anticipate how well he'll perform in NBA games as a 36-year-old coming off a devastating injury. He's never been a strong defender and has been outright bad on the defensive end since turning 30. Can Lillard fit as a complementary player, or will Portland disrupt their flow by catering to a franchise legend past his prime?

2. What will the team do about its glut of point guards?

Lillard was the Blazers' starting point guard for 11 years before demanding a trade after Portland used its No. 3 overall pick on guard Scoot Henderson. The 22-year-old Henderson has shown flashes of star potential but simply hasn't been consistent. During the playoffs, he scored 31 points in a Game 2 win against the San Antonio Spurs — and zero points in a Game 4 loss.

Portland also has point guard Jrue Holiday signed for the next two years, his age-36 and age-37 seasons, for $72M. That means the Blazers will be paying almost $62M next season just to their point guards. For financial and playing time reasons, expect at least one of those guards to be traded, with Holiday the most likely candidate.

3.  Who will be Portland's head coach?

Tiago Splitter took over for Chauncey Billups and went 42-39, leading the Blazers to their first playoff trip in five years. He needs a new contract amid rumors that the team's new owner doesn't want to pay the market price for a head coach. Splitter has made it clear he wants to stay. If the team wants to keep him, the clock is ticking as other coaching jobs open up.

4. Can the Trail Blazers improve their miserable shooting?

Portland was the second-worst shooting team in the NBA last season. They were third-worst in three-point percentage and 24th in free-throw percentage. The Blazers compensated by finishing second in offensive rebounds, and with Deni Avdija getting to the line for 9.2 free throws per game, but in the playoffs, they got outrebounded while shooting just 40.3 percent.

Perhaps Lillard's return will solve this issue. Regardless, having capable three-point shooters on the bench should be a top priority.

5. Will new owner Tom Condon spend money for a contender?

Tom Condon took over as Blazers owner just before the end of the season and made a series of cost-cutting moves, and league sources say the NHL owner was shocked at the cost of running an NBA team. Will Condon be willing to pay high salaries or exceed the luxury tax to compete? His decision on Splitter and this summer's trades will provide some clarity either way.