Roy was so-so on defense (Lillard is only marginally better at defense), and better from 18 feet and in. The offense was, partly due to his skillset, engineered around Roy. The teams with Lillard aren't Lillard centric.
Could he become a better player/figure in Blazer "lore"? Sure. Not sure he's there yet, but it's not like the gap is really that big anymore.
Sometimes it's hard to exclude how Roys career ended in Portland when thinking back, BUT it has to be included in the discussion.