In 2018, the NHL had their hands tied from a concussion lawsuit that came about by a group of 318 NHL players.
To defend themselves in the lawsuit, the NHL spent nearly $100 million.
After winning the lawsuit, the NHL was looking to be insured on that money, but to this day have only received $20 million in return, which is known thanks to a post from Rick Westhead.
This isn't a terribly large amount of money for the NHL, but still, no one wants to lose $80 million.