Al "Scarface" Capone, notorious Chicago gangster and probable architect of the 1929 St. Valentine's Day Massacre, had his fingers in numerous illicit "pies": illegal gambling, prostitution, and, most famously, bootlegging. In his book Blowing Smoke, author Michael J. Reznicek writes that Capone himself estimated that he spent about $30 million (USD) per year -- half of his profits -- on bribes to public officials to escape arrest and prosecution. That's nearly $398 million (USD) in 2015 dollars.
Capone was finally arrested for tax evasion, and that was the only charge that ever stuck. Because of his enormous power and influence in Chicago, witnesses were reluctant to testify against him, and he dealt in cash, never leaving a paper trail that could be traced back to him. In fact, when the St. Valentine's Day Massacre was going on, he was at his winter home in Florida. He even had a doctor write a note saying he was bedridden, and therefore he couldn't have had anything to do with the murders. George "Bugs" Moran, Capone's arch-rival, who was supposed to be in the garage on the day of the murders, told reporters, "Only Capone kills like that."
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