I learned something new: The Stanley Cup has chaperones. It would be like going on a date with someone and having their mother or father join you for the process-- a little bit of a buzzkill.
Back when the trophy was first commissioned, in 1892, by Sir Frederick Arthur, Lord Stanley of Preston, or just "Lord Stanley", he mandated that the trophy be in the care of two "trustees" to make sure it was well taken care of and kept in it's proper condition. This is still true today! The players have limited time w/the Cup.
For 100 days during the year they can do whatever they want with it. Hopefully they are respectful, but some players have gone swimming with it, among a myriad of other odd things.
The rest of the time, it is w/one of the "Keepers of the Cup", a representative from the Hockey Hall of Fame. Philip Pritchard is the current representative, which he's been since 1991.