"Trader Bob" was the last GM that the Blazers have had who had the balls to take risks. He shot for the moon and nearly got there in 2000. His famous quote was "I'm not a chemist" when asked about how the players he gave Mike Dunleavey would fit together. He went out and got the best players he could find and trusted the coaching staff to make the puzzle pieces fit.
Every GM that the Blazers have had since then has been calculated, weak, scared. They either remember or were told the last time the team crashed and burned (2004-2007), they nearly sold the team/defaulted on the RG mortgage/moved to another market. Portland NEEDS the arena to be filled. They NEED the merch sales to be strong. They NEED local TV ratings to be high. Otherwise the talk will start again. And the team is scared shitless of that happening again, so they'll do whatever it takes to keep the on-court product competitive, playoff-good but not championship-good. Play up the "us against the world" mantra to compensate. Celebrate first round series wins like the season was a success. But they'll never take those Trader Bob risks again. And us as Blazer fans have to accept that.