There reason I focused on winners with superstars is because that is a huge topic of debate here -- signing or extending great players and how they correlate to trophies and banners. Of course, I'm one of those fans of this entertainment product who values the journey as much as reaching the ultimate destination (I'm selfish and want to enjoy as many journeys as I can while I can).
111 Teams in the Divisional Era (1969-2019) had at least two pitchers at 5 WAR (there were only 45 clubs with two pitchers at 6 WAR); only 6 of those teams won the World Series. So 5% of the time a team with at least two superstar pitchers wins it all. Or 95% of the time they don't...
11 teams had three pitchers at 5 WAR; only one won a ring -- 2019 Washington, with Strasburg, Scherzer and Corbin -- 9%. That also means teams lucky enough to have three Top Ten-quality starters lose their last game 91% of the time.
1969-2019 World champs with 2 pitchers of 5+ WAR: '16 Cubs, '04 Red Sox, '01 Dbacks, '85 Royals, '69 Mets.