Gambling Man
My supervisor at a company that does contact work inside plants, we’ll call him “M.” M is notoriously bad with money, not malicious, just sometimes he really doesn’t realize what he’s doing.
Anyways, he “borrowed” $500 from the company to treat our clients to a nice meal while he was on an out of town trip, ended up blowing it all at a casino. Company found out. All they made him do was pay it back. He still works there, and this was not his only mistake. Story credit: Reddit / mjsusko