That's the most annoying comment in the world right up there with, "you can't rebuild in Montreal"
Okay, #1
No, of course tanking doesn't work EVERY TIME. Why? Because you need a smart management team in place. You need some bounces to go your way from lottery balls, to puck luck. Sometimes the other tanking teams do it better than you. There's also 31 teams in the league, only one winner every year.
If tanking worked every time, then literally every team would be doing it the minute they got bounced in the first round. Which then, if you have 5 tanking teams, with new teams tanking every year, the math doesn't add up.
#2
You absolutely can rebuild in Montreal. You just have to be up front with the fans about it. Knowledgeable people accept a plan that is well thought out and has a definable strategy. Not something like "get better attitude and more character" and then "if I told you, I would have to kill you."
#3
You can't win the Stanley Cup without a legitimate #1 C. It doesn't happen. Cinderella runs also almost never end up in a Stanley Cup win. The last time I can think of one was the Carolina Hurricanes, they were still a tank team, lead by #1C Eric Staal, and they happened to have the stars aligned where they also met a cinderella team in the Cup Finals.