Ok, ok, try this.
The Montreal Canadiens are a massive money-making machine irrespective of performance. As we've seen with franchises like TO and NYR, this can create a culture in which, while everyone involved would like to win, winning isn't internalized as life or death. This results in people in management playing internal political games, jockeying for influence, protecting their allies from accountability, making hockey decisions based on ego rather than excellence, etc, etc.. Over time this corrodes the entire operation.
That we have seen zero accountability in management - Therrien being protected long past the point when a serious organization would have canned him, Lefebvre remaining firmly in place despite a dismal track record - and dumb hockey moves driven seemingly by ego (Subban, Markov) - all suggest that this dynamic is a major factor in explaining the Habs' stagnation.