I thinking retiring jerseys should be very exclusive. Like, era-defining star exclusive. If I were in charge, I'd probably only have Walton's, Drexler's and, eventually, Lillard's jerseys retired. No one else's. Pippen (my favorite player of all-time) wasn't a superstar in Portland, Roy didn't last long enough, Aldridge wasn't really era-defining--either for the NBA or even for the Blazers. I think Roy and then Lillard were more defining for the stretches of Blazers success that Aldridge was around for.
Now, if the Blazers established a Ring of Honor or a team Hall of Fame, I'd put more players into that. Roy for sure. Aldridge for sure. Sheed for sure. Maybe Pippen. All the core players from the championship team. Terry Porter. That kind of thing.