What follows is the almost unbelievable life story of an uneducated immigrant from Sicily who arrived in the United States penniless, unable to either read or write English, but whose God-given talents and natural savvy eventually catapulted him to tremendous business success, wealth and power.
Born in Sicily in 1903, Carlo Pietro Caputo had little formal education and was largely illiterate when he arrived in America. Yet during the course of his lifetime, this quiet, unassuming little man became an extremely accomplished businessman and one of Madison, Wisconsin’s wealthiest citizens…maybe its wealthiest.
Early on, most people probably wouldn’t have batted an eye at the little Italian immigrant walking the streets of Madison. But as the years went on, those same residents came to understand exactly who Carlo Caputo was — and the tremendous influence he wielded over their city.
This is his story.
Or, more precisely, one part of it.
Caputo possessed an unrelenting determination and tenacity to succeed, coupled with an acute business acumen for organization and a keen logic that allowed him to rise far beyond his humble beginnings. By the 1940s and 1950s, he had become Greenbush’s real estate giant, building a legitimate business empire that eventually dwarfed even his mysterious meteoric rise to “official” Cosa Nostra boss over Madison’s criminal underworld.
Button Guys has written extensively about Carlo Caputo before, including his underworld activities and his rise to become the “official” Cosa Nostra boss of Madison. But this story has a different focus.
Was Caputo a core member of that shadowy Sicilian-oriented criminal fraternity? Absolutely. But this isn’t another “bang-bang” shoot-em-up gangland tale about rackets, racketeers, mayhem and murder.
This is the story of what Caputo built. How a penniless Sicilian immigrant took the profits from his early criminal activities and parlayed them into legitimate businesses, then used those profits to build an increasingly vast business and real estate empire.
In many ways, it is the story of one mafioso’s pursuit of the so-called “American Dream” — a man determined to advance himself, his wife and his children far beyond the humble circumstances from which he began.
If ever there was a mafioso or gangster who fit the bill as “a puzzle, shrouded in a riddle, wrapped in a mystery, hidden inside an enigma” — Carlo Caputo was that guy!
A Life Built Around Shadows and Mystery
Born September 21, 1903 in the little town of Bagheria, on the outskirts of Palermo, Sicily, after immigrating to the United States at age sixteen Caputo made his way to the City of Chicago, Illinois.
This is where he would start his new life in America. It is also where Carlo is believed to have first become affiliated with members of the newly transplanted Sicilian underworld.
With the advent of the Volstead Act, implemented by the U.S. Congress in 1920 which made it illegal to manufacture, possess, sell, or drink alcoholic beverages of any kind, the multibillion-dollar bootlegging racket started to take hold as a major new business for America’s criminal underworld.
And among thousands of others to capitalize on this new “industry” in the coming years, Carlo Caputo is believed to have become extremely active as a Chicago-area bootlegger.
Often Imitated. Never Duplicated. Button Guys of The New York Mafia...There's Only One!
