A list of the wealthiest Americans who failed in politics, with photos. These are wealthy individuals who tried to win public office with their vast wealth, but failed. As this list shows, wealth is anything but a guarantee of winning a government election. Ross Perot spent an estimated $64.4 million of his own money. This list is not adjusted for inflation, but all of the entries are relatively recent. Wealth may sometimes lead to power, but for the would-be politicos on this list it certainly didn't.