How Spitzer Was Caught:
Of all the ironic aspects of the Elliot Spitzer scandal, I think the most remarkable is how he got caught. Based on stories like this and this, it looks like Spitzer got caught because the prostitutes he hired were so expensive that he needed to shuffle several thousands of dollars around each time. Spitzer knew that banks report suspicious money transfers to the IRS to combat financial frauds and money laundering, so he tried to structure his money transfers to avoid suspicion. But the banks thought his activity was still suspicious, so they reported him and the IRS opened an investigation under the assumption that Spitzer was trying to launder money he had obtained from bribes. But he wasn't laundering money — he was paying prostitutes. So Elliot Spitzer, aggressive former white collar crime prosecutor, was brought down because he couldn't outsmart banks looking for evidence of white collar crimes.