During Trail Blazer General Manager Neil Olshey’s contentious, often confusing, Monday press conference, a reporter asked about the possibility of trading Damian Lillard if the team does not improve in the next three seasons.
Olshey declined to answer a question that five years ago would have been egregious to ask. Why would Rip City trade the greatest player in their franchise history? But this latest off-season has put that possibility in a new light.
Lillard will be 31 years old at the start of next season.
During his nine year career, the superstar has made the Western Conference Finals once. Four of those years have included first round exits from the playoffs. Dame’s prime will last no longer than three more years before a natural decline in physicality takes old.
That’s a three-year window to not only make at trip back to the Western Conference Finals, but make a Finals appearance that’s worthy of his talent.
Neil Olshey didn’t indicate any more willingness to take big swings in free agency and the trade market. For Lillard to bring a title back to Rip City, it would require another All-Star caliber player that has defensive capabilities and complementary scoring attributes. Think Karl Anthony Tonwnes. Would Olshey and the organization take a chance by moving CJ for Townes? Olshey’s presser shouldn’t lead you to believe in the affirmative.
No matter where you fall on the “Damian Lillard Trade Spectrum,” the state of Portland’s program should be cause for concern when it comes to the Superstar’s future here.



