The Stanley Cup logo is the bear with the flying wings and a crown on its head, it came from the inventor of the Stanley William Stanley Jr. William went camping with his wife and he had a few drinks and then went back to bed. He woke up in the middle of the night and heard rustling around the tent. He saw a mythical bear with wings. He reached for his Stanley water bottle and aimed for the bear. Instead He hit his wife, his wife angrily hit him back and then they both were very dizzy and “Saw stars.” The bear left and was never seen again. 

He probably was just drunk and was seeing things and didn’t know what he was doing. Apparently the Stanley website as a letter from the creator himself. And it went like this,

Dear Stanley,

My wife and I went camping. After a few drinks and swinging some tunes around the campfire, we decided to turn in for the night. I was fast asleep and could have sworn I was dreaming when I heard something ruffling around the tent—it was a bear. I woke up with adrenaline running through my veins, reached for my Stanley, and turned in the dark to hit the bear. I was aiming to be a hero, instead I ended up hitting my wife on the head. Well, she turned and whacked me on the side of my head. While the two of us saw stars, the bear didn’t want any part of this and hit the road.

Sincerely,

The guy with a wife tougher than his Stanley bottle