The team is its own worst enemy.
Decades of players, coaches, GMs, presidents, owners, philosophies, strategies, etc. Nothing works. Everyone in a leadership role is out for themselves. The league sees the franchise as a cash cow and nothing more, willing to openly spit on them, because they know they will get their money no matter what.
Bettman looks at the Leafs and sees dollar signs. Owners and managment look at the Leafs and sees dollar signs. The media looks at the Leafs and sees dollar signs. The players look at the Leafs and see dollar signs. The fans bend over and hope something will change.