I know a guy that did. He mentioned to someone I know that he would like to pay her rent for a month because he knew she had been struggling, but he told her not to ask him any questions and it was going to take a few weeks to get the paperwork processed. She told me about it, and we kind of figured he'd somehow been scammed. A few weeks went by, he showed up with paperwork in his hands, and said once he had contacted his lawyer to look over the paperwork, he'd be able to pay her. Since he had paperwork & a lawyer now, it seemed more legit.
A few months later, he told her he had been scammed. He had gotten a phone call saying he'd been chosen as a sweepstakes winner for a large sum of money and they were sending him the paperwork which he needed to fill out and have overlooked by a lawyer but in the meantime, they wanted him to pre-pay the processing fees and to set him up with installment payments on the taxes to "satisfy the IRS until he got the large sum of money & could then pay the rest of the taxes owed".
He gave them his banking info, etc. They ripped him off & was gone before the lawyer could tell him he'd been scammed. The poor guy was devastated, he's retired and lost money that he couldn't afford to lose. He said he always enters all the contests he sees, so when he got the call saying he won, he really thought he did.
I keep track of the contests I enter now, and the prizes, and their method of contacting the winner and I keep it to no more than 6 a month from reputable businesses/websites.