I am a McLaren fan here and regarding 2008 it would have been totally undeserved for Massa to win the title at that time.Every single duel on track against Hamilton he came out as a loser and he had the better car back then,Ferrari was just a bit better than McLaren.It was only luck that sought Massa to fight for the title and the funny thing was the local Brazilians gifted to Hamilton a Vasco de Gamma T-shirt meaning they were the eternal seconds in Brazil Serie A so hopefully even Hamilton was going to have a fate like that.Hamilton accepted it and he didn't care at all about that superstition and he became World Champion.
For 2021 I cannot say that Lewis deserved the title more than Max or Max more than Lewis but circumstances brought the title to Max and that is it,just that.
I already don't remember whole 2008 season as good as you, so, I won't argue whether Massa was worth to win it or no. But the way he lost title was really heartbreaking. Winning last race at home track, Ferrari already started to celebrate title and then Timo Glock happened.
And I didn't hear story about Vasco de Gamma T-shirt, that's interesting story.