Just one day after trying (and failing) to land Avalanche free agent Ryan O’Reilly with an aggressive offer sheet, Jay Feaster and the Calgary Flames found themselves in the center of a controversy over whether they’d almost committed an all-time blunder.

According to a report, the Flames would have had to place O’Reilly on waivers as soon as they signed him. That means Calgary would have given up the draft pick compensation and the $2.5 million signing bonus, only to see its new player immediately wind up elsewhere. That didn’t end up happening, because the Avalanche matched the offer sheet, robbing us all of what would have no doubt been a fascinating legal scramble, but the incident embarrassed the Flames and has fans calling for Feaster’s head.

All of which puts Feaster & Friends in good company. After all, NHL hockey is complicated business, and the Flames’ offer-sheet saga certainly wasn’t the first time that somebody in the hockey world found themselves getting tripped up by a legal loophole.

Whether it was through confusion, dishonesty, or just plain old incompetence, here are some infamous moments in NHL history that had fans and team officials alike scratching their heads and checking their rulebooks.

Welcome to a weekly blog post of thoughts and observations from the past few days and/or decades of NHL hockey.

The Three Stars of Comedy

Recognizing the three moments or personalities from around the league that produced the most comedic fodder for fans this week.

The third star: Ryan O'Reilly’s dad
It’s always entertaining when a young player’s parents decide to get involved in his contract dispute. For some reason, it’s even better when they decide to do so via Twitter. I’m just disappointed we didn’t have social media when Carl and Bonnie Lindros were in their prime.