There have been four players to lead Portland to the WCF: Walton, Drexler, Sheed, and Dame. Four ever. In fifty years. The best players Portland's ever had were either drafted by them or acquired by them via trade very early in their careers.

Portland's not a huge free agent market. They won't sign the Brons and Durants. They are as good as the talent they develop can make them. It's in their best interest to tell Lillard, "You're a lifer." Because they don't have realistic alternatives.