Respectfully disagree.
The Bruins during much of Orr’s career are seen as a “what could have been” team, winning two Cups when they should have won four in the early-1970s. They are even the first established/O6 team to lose in the finals to an expansion team (Flyers in ‘74). Honestly, despite two Cups, that Orr/Esposito led team is often viewed as a major underachiever.
The Red Wings, on the other hand, were never even once the SC favourite after their 1955 finals win over the Habs. Nevertheless, even after Jack Adams systematically destroyed the dynasty team’s roster, Howe led the team to the finals 5 times in 11 seasons (‘56-‘66, when Howe was 28-38 years old). For his career, the Wings lost in the finals 7 times (twice to the late-40s Leafs dynasty, twice to the 60s Leafs dynasty, twice to separate Habs dynasties, and once to the Bobby Hull led Hawks).