The Portland Trail Blazers are looking to assemble a championship-caliber team centered around their star player, Damian Lillard. In pursuit of this goal, the team made a flurry of trade deadline moves this season to acquire future assets, despite the potential for short-term roster imbalance.
The Blazers have encountered many difficulties in the 2022-23 season, but they remain focused on building a contender moving forward.
They recognize the need to bolster their roster to achieve their ultimate goal. The Blazers will need to make some smart moves this offseason to add depth to their roster and become a true championship contender.
There are many potential roster changes on the horizon, with several Blazers becoming unrestricted free agents soon. The front office will need to make some tough decisions about which players to retain and which to let go in order to build a team capable of bringing a title to Portland.
1. Justise Winslow
Justice Winslow was part of the questionable Norman Powell trade. While he’s brought energy to the team in games he’s played, he may not be a Blazer next season.
Winslow’s contract with the team is expiring. He has only played 29 games this season due to injury, and this lack of availability could make the Blazers hesitant to commit to him long term.
The team would likely prefer giving a contract to a player it can count on after injuries contributed to Portland’s poor record this season. Overall, Winslow’s injury history and contract status may make it challenging for him to remain with the Blazers next season unless he’s willing to take a minimum contract.

2. Nassir Little
There are a few reasons why Nassir Little may not be with the Trail Blazers next season. If the Blazers retain Cam Reddish and Matisse Thybulle with qualifying offers, Little’s role on the team may be redundant. Although a young player with potential, Little may not have the same level of established skill as Reddish and Thybulle, making him more expendable on a crowded roster.
Additionally, Little’s team-friendly contract could make him an attractive asset in trade discussions for a star player. The Blazers would need Reddish or Thybulle to agree to a trade if they sign their QO’s, but they wouldn’t need Little’s input.
Ultimately, while Little has shown flashes of potential, the Blazers may prioritize using him to acquire a player who fits better with Dame’s timeline.

3/4. Anfernee Simons and/or Shaedon Sharpe
Shaedon Sharpe and Anfernee Simons are beloved players and are key pieces on a rebuilding team. With the Blazers attempting to build a contender while Lillard is still in his prime, though, Sharpe and/or Simons may not be with Portland next season.
Rather than wait for Sharpe and Simons to fully develop, the Blazers may view them as highly valuable assets that could be used in trade discussions for a superstar player. As talented young players with high upsides, Sharpe and Simons may be the most enticing pieces for any potential trade partner.
If the Blazers truly prioritize a win-now mentality and a superstar becomes available via trade, Sharpe and Simons are the two best players they can offer.
Ultimately, while both players have shown promise and potential and are loved by fans, their value to the Blazers as trade assets may lead to their departure from the team in pursuit of a star player.
Ideally, though, the Blazers retain one of the two to take the shooting pressure off of Dame in the backcourt.

5. Jerami Grant
Budding star and fashion icon Jerami Grant may not be with the Trail Blazers next season. Although the Blazers have shown interest in retaining Grant by offering a max contract, he is on an expiring deal. If the Blazers are not able to agree with Grant on a new deal, he may choose to sign with another team in free agency.
Grant may not believe that the Blazers have a realistic chance of contending for a championship soon. If he views his current situation as a potential roadblock to achieving his goals as a player, he may choose to seek out other options that he feels are more aligned with his objectives.
Ultimately, Grant’s future with the Blazers may hinge on the team’s ability to demonstrate that they are committed to building a winning culture and have a clear path to contention. If he feels confident in the Blazers’ direction, he may choose to stay with the team, but if not, he may seek out other opportunities.

