I've seen people sharing stories about bosses expecting employees to pick up the cheque recently. Here's mine.
The store owner decided to have the Christmas party at a local restaurant – buffet, one free drink, raffled prizes (that turned out to have been returned items with too much packaging damage to be reshelved…here we go). At the end of the night, I was talking to my department manager when the restaurant owner asked him who would be settling the bill (for the whole party). The owner had left an hour ago, and we'd all assumed he'd already paid.
It took nearly an hour to get him on the phone, and he was annoyed that we'd bothered him. He didn't want to drive back, so could one of the managers just cover the tab and he'd pay them back (knowing him, that would never happen, at least not fully). My manager told him none of his employees have that kind of money, so owner's solution was to take a collection. The millionaire wanted his minimum wage employees to pass the hat to pay for their own Christmas party. Can't say I miss that guy.