I thought Ford was pretty generous on this one. The Blazers went from a mid-to-late lottery team to a mid-to-late lottery team. I loved the Blazers' draft (even though Meyers Leonard will primarily be a rebounder/shot blocker for his first few seasons), was thrilled to see the Blazers finally bring Joel Freeland and Victor Claver from the Spanish League, and Olshey didn't destroy the Blazers future cap room.
But ultimately, none of that can disguise the fact the Blazers failed to make any significant moves to make them into a championship contender. Barton, Hickson, Claver and Freeland will be decent, cheap backups, and Lillard has a chance to be very good. But the Blazers missed out on Roy Hibbert and failed to land any other All-Star caliber talent.
Did the Blazers have a bad offseason? No. But they didn't rebuild nor did they reload. All Olshey did this offseason was reshuffle, and didn't do anything to push them back towards relevance.