They simply spend beyond their means.
You have a great tagline!
I haven't had a negative net worth since the first couple of years out of college, and I didn't get an especially auspicious start to my career. These are supposed to be fairly accomplished people. No wonder they're prone to corruption, they can't rub two nickels together.
I imagine much of the negative net worth is actually huge jumbo mortgages on big fancy houses. Sure they can't afford them, but they get the best rates (with supporters buying the view lots next door, like Obama has) so in a sense it's just another too-good investment not available to ordinary citizens. Like Clinton's cattle futures.
Great tagline...don't you mean public school?