Kyle has tied himself inextricably to the core and the Big Four salary bias. Those players themselves are less responsible for the lack of post season success than their salaries which put down force on the rest of the lineup. All that comes back to the GM because it isn't those four forwards, its $40M on four forwards. I don't see how another bad playoff doesn't cost him his job as that would require MLSE to accept "sorry about the last five playoffs, I am going to move the big piece(s) I said I would never do and build somebody else's dream lineup". If they need a new direction, I can't see any reason why they would choose KD to take them there. His salaries, his lineup, his coach, his goaltending solution.
It seems counterintuitive that ownership wouldn't start at the top because that seems to be the norm in pro sports. Just because it hasn't been leaked to a media insider doesn't mean this isn't the 11th hour. There is still time to fix things but they have a much tougher path ahead of them than last year.