jokeboy86 wrote:Only question I have is for Blazers fans.  If Dame plays out this contract but never reaches the Finals or a conference final again would the loyalty and longevity make you put him over Drexler and Walton?
In a word, no.
Clyde Drexler still is the all-time leader or in the top five in a lot of team categories despite leaving Portland nearly 30 years ago. He also led Portland to its greatest three-year streak of three consecutive Western Conference finals (1990-92) and two NBA Finals against two legendary squads (Bad Boy Pistons in 1990, Michael Jordan's Bulls in 1992). Drexler also was MVP runner-up to Jordan in 1992 and has the historical reference of being on the 1992 Dream Team (meaning he's been inducted into the Naismith Memorial Basketball Hall of Fame twice).
Bill Walton led Portland to its first playoff appearance in 1977 and it culminated in the Blazers' sole NBA title, a win over the juggernaut Philadelphia 76ers team featuring Dr. J, George McGinnis and Doug Collins. Walton also was the league MVP the following season and the Blazers were 48-10 before he broke his foot.
Since Damian Lillard has been the top player since LaMarcus Aldridge left, Portland has been to the playoffs six times and eliminated in the first round four times. The Blazers never have been more than a team that had a second-round peak with Lillard as the best player. Even with the 2019 Western Conference finals team, it seemed like a second-round team that got a favorable break (won the tiebreaker with Houston to avoid Golden State in the early rounds), and the Blazers barely beat a young Denver team in the second round where C.J. McCollum led Portland from a large Game 7 deficit while Lillard went 3-for-17.
Also, from a historical sense, I regard Drexler as one of the top five or six shooting guards in NBA history. I don't believe anyone will look at Lillard as being one of the very best point guards in NBA history. 
Walton is one of the great "What If?" stories in NBA history where Portland fans still think the Blazers could have won more titles with a healthy Walton. Walton also has been the poster child of Portland's laid-back, counterculture spirit for decades and always will be known for putting the TrailBlazers on the NBA map with the 1977 title. Lillard leading multiple teams to first-round exits and the 2019 team getting swept by Golden State can't compete with that.