The Business of Al Capone

Retired Intelligence Detective Gary Jenkins brings you the best in mob history with his unique perception of the mafia. In this episode, we take a deep dive into the book “The Outfit” by Gus Russo, which explores the life of Al Capone and sheds light on the hypocrisy of the American justice system and the robber barons of the era. Capone ran his bootleg empire like a corporation, complete with divisions, managers, and a division of labor. He even had a political lobbying arm and a succession plan in place. Frank Nitti, who came from the Brooklyn to Chicago gangster pipeline, played a significant role in Capone’s organization. Starting as a barber, Nitti eventually became a top-shelf whiskey smuggler and took over as boss when Capone went to prison. However, the pressure of being the boss took its toll on Nitti, and he tragically committed suicide after taking the fall for a Hollywood extortion scam.

Capone often compared his organization to supposedly legitimate companies and robber barons of the time, highlighting their mistreatment of employees and battles against labor unions. It was an era with few federal regulations, allowing businesses to operate as they pleased. Capone even influenced dairy companies to put expiration dates on milk bottles after his niece fell ill from rancid milk. These parallels between so-called legitimate companies and mobsters are fascinating, as they both operated with little concern for the well-being of others.

In another part of our conversation, we delve into corruption involving banks and robber barons. During the time of the failing banks, certain individuals encouraged people to put their money into another bank that would also fail, yet no legal consequences were faced. We also discuss Joseph P. Kennedy, who engaged in unethical practices to acquire a chain of film theaters and was involved in bootlegging. Although he was initially convicted on false charges, his conviction was later reversed.

Regarding Joe Kennedy’s involvement in bootlegging, there is limited concrete evidence, but we do know that his father had a bar and a wholesale liquor business. Kennedy seized the opportunity to capitalize on liquor sales during Prohibition until it was lifted. He then made a significant profit through exclusive contracts with British distillers. In comparison, Al Capone had a different approach to illegal activities.

We want to give special thanks to Ben Ellickson for providing us with valuable reading material on this subject. Ben has also proven a great friend through his thoughtful gift of a Prohibition-era glass whiskey bottle and his expertise in operating a backhoe.

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