As each day of the off-season goes by, Damian Lillard's future grows more uncertain. Each week, we get reports of Lillard wanting a trade, only for Dame or a source close to him to come out and deny those reports. But it looks like Lillard is the more credible authority at the moment. Lillard has had opportunities to leave the Trail Blazers but chose to stay with them because of his love and loyalty for the franchise.
Realistically speaking, Lillard will find it difficult to help the Blazers create a championship-caliber squad in Portland because of the fact that it is a small market and not a major free-agent destination. But despite this, all indications are that Lillard will continue to play for the Blazers next season, barring any surprises.
In fact, Neil Olshey, an executive with a close relationship with Damian Lillard says he expects him to stay. In an interview with Jason Quick of The Athletic, Olshey noted that he expects Lillard to stay because of his legacy with the franchise. But despite his desire to stay, the front office cannot get complacent.
They need to make moves in the off-season with the assumption that Lillard will leave to bolster the urgency of their process. Olshey and Lillard have always had an open channel for communication, with Lillard often discussing the franchise's plans during the off-season with him.
“I don’t think he wants to leave. He has built an empire here. But we have to assume he is leaving to make sure he is not leaving.”
Olshey will be a good authority on where Lillard stands on his future with the franchise. The two met twice during the summer so far, including one meeting that involved new head coach Chauncey Billups. And if Olshey didn't get any indication that Lillard wants to leave, then he can continue to work to improve the team around him.