I’m not sure the NHL has a weirder annual award than the Mark Messier Leadership Award for Outstanding Achievement in the Field of Leadership.
It’s not quite a slam dunk, because the Lady Byng exists. But at least that award has been around for a century, and is voted on by a pool of writers who’ll always get it right because democracy never fails. The Mark Messier is a relatively new award that, as far as anyone can tell, just goes to whoever Mark Messier himself deems worthy. What’s the criteria? Nobody really knows. Leadership, apparently.
The award started off in 2006 as a monthly honor, before quickly being retconned into a more traditional annual award.