Under no circumstances should you find yourself purchasing a briefcase that has wheels. In fact, there aren’t enough alternate planes of existence in the entirety of endless space to ever find one single instance where I will say, “Yes, you should put that briefcase on wheels.”
But, for the sake of argument, let's say you do you find yourself at that crossroads, contemplating whether or not you should buy a briefcase with wheels, do us all a favor and retire. Go fishing or something. Go play chess at the park or throw bread at the ducks or complain about the price of a pound of cauliflower to no one because you're the worst and you have no friends. Just please do not buy one of those goddamn rolling briefcases so you can roll over my toes and break them into a million pieces and ruin my goddamn day.
In case that rambling unstructured and unintelligible opening wasn't enough a reason to never buy a rolling briefcase, after the jump are five more reasons why you should never, ever own a rolling briefcase.