I don't think it's fair to say how things will play out with any level of certainty (which is, of course, part of what makes the Stanley Cup playoffs interesting).
There are so many examples of the razor thin edge between winning and losing, greatness and mediocrity--and of us imposing the narrative after the fact.
That Bruins team that we lost to in 2013 was by any definition a good team; they had a great lineup and went all the way to the Cup final...but just to get out of the first round they needed a totally improbable third period comeback and OT win against an inferior Leafs team that hadn't made the playoffs before under that regime and didn't make it again. If Matt Frattin scores on that breakaway...or James Reimer makes one more save in the 3rd period...or Joffrey Lupul scores in OT instead of hitting the post and the Leafs win that game/series, were they any better than the team that didn't but instead collapsed so embarrassingly?
In 2018, when they won the Cup, the Capitals fell behind to Columbus in the first round 2-0 and Game 3 went to double-OT. If they give up the OT winner in that game (which of course they easily could have) and go down 3-0, they almost certainly lose that series and go out early yet again. Instead they completed the comeback, won the series, and never looked back. The legacy of the Ovechkin Capitals is totally different if things go just a little differently in that Game 3. History now sees them as a team that overcame adversity and learned how to win instead of a perennial choker. But that's B.S., really; they just took advantage of the right break at the right moment and went on a run at the right time.