Capone made as much as $100 million a year (equal to $1.3 billion in 2016 dollars). At one point in the 1920s he paid out $500,000 per month (worth about $6 million today) to police to let him operate his illegal booze trade.
Kennedy, whose nine children included President John F. Kennedy, and U.S. Senators Robert and Edward Kennedy, made his early fortune as a bootlegger during Prohibition.