The NBA title is the hardest title in Major sports to win.

The big difference with hockey is that a hot goalie can make a difference waaaaay out of proportion to the percentage of the players on the ice (one out of six at a time, or one out of 19 total, if you are shifting three lines of defensemen and four lines of forwards). If you look at the number of times that lower-seeded teams (five or below, assuming eight teams from each conference) make the Cup finals, you'll see the effect a hot goalie can have.

On the other hand, while great players can and often do have a tremendous effect on the outcome (one thinks of Michael Jordan or "Shaq & Kobe"), these players are usually on teams that were also top-tier teams during the regular season, showing the same level of personal dominance in leading their teams in all phases of play, as opposed to a specialty position like goalie.

So yes, to me it is fairly clear that the NBA playoff system is the one most likely to produce a champion that is a deserving team based on its regular season play, and thus the hardest to win.

The NFL is a clear second, and baseball (hot pitchers) and hockey (hot goalie) are much, much more likely to make the regular season meaningless.

Wouldn't the fact that the regular season is meaningless in the NHL mean that it's harder to win the Stanley Cup? If playing hard all season does not necessarily lead to playoff success then it seems to me that it is harder to win. In the NBA the team that is dominant in the regular season is usually dominant in the playoffs which means it's not really that hard for them to blow through the playoffs. On the other hand, an NHL team that dominates in the regular season can run into a hot goalie or two making it much harder for them to win the Championship. That in my book makes it harder to win the Stanley Cup.