Honestly, how the heck does the PP go so long without being addressed? How can anyone not stop and think "Okay, this isn't working, let's shake this up" at a professional level when millions of dollars are on the line and a single game can cost you a playoff berth? I'm not much of a hockey guy anymore, so I don't really follow the Leafs that closely, but even in baseball you can see the coaches and players trying something different if things aren't working after a month or so. Heck, even legendary players will be benched if they're playing that poorly.
In my experience in corporate research, usually hiring structures like that are the result of "my buddy" appointments; ie, the suits above are giving their friends the best jobs regardless of their actual skill or production. Not all that different from "yes men" appointments. I don't really know the Leafs corporate structure because I never liked them as an investment, but given how many old guys are in charge there, I wouldn't be surprised they are also hiring old school.