It's astonishing that any large company would look at a track record of high-level, very well compensated managers and see nothing but failed expectations and say, "Okay, guys, keep it up and we'll see you at the end of next quarter."
What better way to push a team to finally get past whatever is holding them back by continuously patting them on the back? If there is no accountability for failure, and clearly there isn't when it comes to the president, GM and coach, then how worried are the players about being held accountable?
DeBoer and Trotz miss the playoffs after taking their teams deep twice in previous seasons and they're fired this year for missing the playoffs. Keefe, coaching a stronger (regular season) team than both Vegas and the Isles, leads his team to a first round exit 3 years running (all against lower seeds) and he's given a pat on the back and "Don't worry buddy, you're going to be a great coach in 10 years!"
As for the players, just one of many examples, how worried is Nylander that despite repeatedly doing everything he can to avoid physical contact throughout his career and never once (that I recall) even being benched for a shift or two to send a message, that somehow he has to change that? He's not worried, he's learned that in the Leafs organization, there is no accountability, no one that will call him out.
When people talk about the Leafs team being soft, it is little wonder why? The organization is soft, from the very top down.