Really dumb "loopholes" people you know tried to do legally/criminally and failed miserably

Well, how will they know it’s stolen until they process the payment? And then the bail is paid, checkmate!

“Hey, while you’re at it, can you just put two bails on that card? K Thx Bye!”

This one doesn’t actually meet the “people you know” criteria of the thread, but some of the schemes in this thread reminded me of a story I heard about the housing bubble of the 2000s: A group of friends were just selling the same house to each other repeatedly, for more money each time. So Person A would sell the house to Person B for say $400K. B would make a couple of mortgage payments, then C would take out a mortgage and buy it from him for maybe $450K. B would pocket the profit, and then a few months later C would sell it to D for $500K. Then D would sell it back to A and they would go around again.

That whole scheme really smacked of “They really didn’t think it all the way through, did they?” Did they really think they could just keep going around like that forever? They had no apparent end game. Obviously at some point the bank was going to expect the mortgage to be paid back. Maybe each of them assumed they weren’t going to be the one holding the bag when that happened. Or they figured they’d just default and let the bank take the house when that finally happened, which of course is what actually happened.

Was that Mrs. Nussbaum?

And this got a lot of banks in trouble, exactly for doing it to add on overdraft fees. US Bank got hit with it, now all deposits go in before debits.

I could see this being useful as part of a pump-and-dump scheme. Buy up 10 similar properties, pump up the price of one of them like this, pocketing some cash at each stage, and then sell all the houses in one big move. “Sure, I only paid $400K for this house, but you can see the average home value has been increasing steadily for the last 5 years! So you must pay $800K. Don’t worry, if the trend holds, it’ll be worth a million in two years!”

Washington Mutual pulled that BS on me in the late 90s when I was just starting out on my own. Things were tight but OK. I hadn’t accounted for a $25 overdraft fee from them purposefully processing the check before my direct deposit. Before I knew it, I had two additional overdraft fees from small debit card purchases that I should have been able to cover.

So it worked?

They did that to me, too. Worse was when Chase bought them, gave us “free checking for life,” and then a few years later introduced a monthly fee to the “free checking for life” accounts (which is when I closed my accounts with them).