Roy overcame mediocre teams. He won in Montreal with mediocre. He won with Colorado with a stacked team. He did both.
Unfortunately for Price, he did neither. If the Habs continue to flounder he may eventually get his number retired but it will not be anytime soon. If it is then the exceptional history is tarnished. There are plenty of good players WITH cups that didn't get their number retired.
Really, when was that?
In 1986 with a team that had the 7th best record in the league, and had 4 future HHoFers (excluding Roy) on the roster?
Or in 1993, when they had the 6th best record in the league? And while I'll grant you that there wasn't any super elite talent outside of Roy, it was a balanced team that produced very well.
And in neither season did Roy carry the team on his back and they only made it that high in the rankings because he was the only reason they won. He had two pretty good years and got some Vezina votes, but he wasn't the only reason he made it that far.
Roy almost never had to overcome mediocrity until the end of his tenure with the Habs.
When Roy was on actual mediocre teams:
1990-1991 - While the Habs finished 6th in the league, they were 11 points behind the 5th best team in the league. Lost in the second round.
1993-1994 - 9th in the league in points, first round exit.
1994-1995 - 16th in the league in points, missed the playoffs.
1995-1996 - Incomplete, traded.
Otherwise, the Habs finished with the 7th, 5th, 2nd, 2nd, 4th, 6th (1990-1991), 5th, 6th, 9th (1993-1994), 16th (1994-1995) record when Roy was here.
When he was in Colorado, his teams finished with the (excluding 1995-1996, they won) 1st (Western Conference exit), 7th (1st round exit), 4th (Western Conference exit), 9th (Western Conference exit), 1st (Champions), 4th (Western Conference exit), 6th (1st round exit) best records in each full year Roy was there. Only one mediocre team his entire time in Colorado.
So in four seasons being on mediocre teams, he's only gotten to the second round once when in Montreal and made it to the Western Conference finals on his worst team in Colorado, albeit a team that had Sakic & Forsberg miss a combined 53 games.
Roy never overcame mediocre teams and led them to victory.