Interestingly, of those three finals (1985/1986; 1988/1989 and 1992/1993) it was the finals that they lost (1988/1989) where Montreal had the strongest (best) team. While I may receive derision from some for my reasoning, I can say that the reasons for the outcomes ( both good and bad) largely rested on Roy, who was at the time, arguably, the best goalie in the world. While supremely helped in their Cup victories in 1986 and 1993 by the upset defeats of the then Stanley Cup Champions , the Oilers and Penguins respectively, the Canadiens couldn't have taken advantage of those opportunities without the play of Roy who won the Conn Smythe Trophy in each of those years. 1989 was a different case. Montreal had assembled what clearly was their best team since the dynastic teams of the late 1970s. They were better on paper than the Flames. Roy was simply outplayed by Mike Vernon in the finals. It looked, at times, like Roy was intimidated by Al MacInnis' shot.
Nevertheless, the Canadiens of 2024, bear some similarities to the reviving Canadiens of 1984 which was able to win the Cup in 1986. Both teams had a core of young, productive veterans, with Canadiens of 1986 having Chelios, Carbonneau, Ludwig, Smith and Naslund and the current team having Suzuki, Caufield, Matheson and Newhook. The 1984 Canadiens had a host of emerging stars and prospects: Richer, Corson and Lemieux while the current team boasts Slafkovsky, Dach, and Guhle and a prospect pool that includes: Demidov, Hage, Reinbacher, Hutson and the Xhekaj brothers which is far deeper and has more upside than what the 1984 team possessed. The greatest question is in nets. It is unlikely that Montreal will be able to obtain a goalie of the caliber of Patrick Roy. That type of goalie only comes along every twenty years. But between Montembleaut and Fowler, the team should have enough efficiency in net to compete.
The future for the current team looks bright, as it did for the gallant, but undermanned 1984 version of the team.
