10 Richest Criminals Of All Time

Anyone who says crime doesn’t pay should take a look at these men and women. This collection of bank robbers, drug dealers, crime lords and general scumbags shows that if you want to get ahead, sometimes it helps to chop off a few heads… (Note: white collar criminals like Bernard Madoff weren’t considered for this list; our focus was criminals of a more hardcore caste.)

10. Joseph Kennedy ($200-400 million, a billionaire figuring in today’s inflation)

Joseph Kennedy was the harmless-looking patriarch of one of the most powerful families in America, a corporate big shot… and strongly connected to the bootleggers who made millions selling alcohol during the Prohibition Era — if not a bootlegger himself. He is widely thought to have had dealings with Frank Costello, the head of the Luciano crime family, to facilitate smuggling alcohol into the country for easy distribution during the post-WWI period. Not only did Kennedy make a profit on his river of illicit booze, but he was also credibly accused of framing one of his rivals for rape in order to acquire his business (not to mention of being a gross anti-Semite and a major supporter of Hitler). Still, with his fortune measuring in the billions in today’s money (in 1957 he was named one of America’s richest people by Fortune magazine) it probably wouldn’t have been wise for the rest of the Kennedys to have disowned him completely…