Not NHL related, but one of the more fascinating documentaries I’ve watched is about the Danbury Trashers (UHL) team in Danbury, Connecticut. I think it’s on Netflix.
The owner, James Gallante, was a garbage disposal mogul and allegedly connected to organized crime. He appointed his 17(!) year old son as GM to run the team. They built a team of brawlers and set a league record for penalty minutes, actually doing quite well in their two seasons. Mike Rupp and Brent Gretzky were recruited to play on the team.
However, Gallante was charged with racketeering after their second season and the team folded.