4. Damian Lillard
Lillard has requested a trade and wants to join the Miami Heat. The Blazers have not shown interest in their best package, and things could get complicated quickly. Dame has a player option in the summer of 2026 for $63.2 million. The seven-time All-Star is locked up long-term, which limits his leverage. If Portland cannot find a deal, Lillard will have to stay with the team, expand his list of destinations, or hold out.
The 6’2 guard likely reports to camp and helps the Trail Blazers until they can find a suitable package closer to the deadline. It may not be the desired outcome for either party, but it appears most likely if no deal is in place before the start of training camp.
Lillard wants to leave Portland after 11 years to play for a contender. The Trail Blazers have missed the playoffs two straight years and figure to be back in the lottery in 2024. If Dame expands his list of teams expect it to feature teams ready to make deep playoff runs.
Ramona Shelburne reported he had “deep respect” for the Spurs back in July. If Victor Wembanyama can quickly become a star, Lillard could be interested in coming to San Antonio. The Spurs need a point guard and have a mountain of draft capital to flip to help them jump into contention. Do not rule it out.