Al Capone

Al Capone's criminal empire in 1920s Chicago generated an estimated $100 million per year — roughly $1.5 billion in today's money. His organization controlled bootlegging, gambling, prostitution, and protection rackets across the city with such efficiency that it functioned essentially as a Fortune 500 company with a murder department. At age 26, Capone was one of the wealthiest people in America. He paid for it with an 11-year prison sentence and syphilis-induced dementia.

The IRS angle is what makes Capone's story a financial masterpiece. Federal prosecutors had mountains of evidence for murder (including the St. Valentine's Day Massacre), racketeering, and bootlegging — but couldn't make any of it stick because witnesses kept dying. So they sent accountants. IRS agent Frank Wilson spent years tracing Capone's spending — the custom suits, the diamond belt buckles, the $7,000 dinner parties — and proved that his lifestyle exceeded his reported income of zero. Capone was convicted of tax evasion in 1931 and sentenced to 11 years in federal prison. The most feared crime boss in American history was brought down by a spreadsheet.

Capone's actual net worth at the time of his conviction was likely $50-100 million. By the time he was released from Alcatraz in 1939, syphilis had so deteriorated his brain that he had the mental capacity of a 12-year-old. He died in 1947 at his Florida estate, still technically wealthy but completely incapable of enjoying it. His family maintained a comfortable lifestyle on his remaining assets for decades. The lesson: Capone wasn't undone by rivals, police, or prosecutors. He was undone by the IRS — which remains, to this day, the one organization in America that literally everyone is afraid of.