In the first two decades of the twentieth century, a scourge to the familia of Little Italy were the Black Handers. Sicilian themselves, their modus operandi was simple but deadly: Residents would receive a knock on the door in the dead of night; when they answered, they would find naught but a letter left on the threshold demanding so-much money to be paid to an anonymous entity who would return on such and such a day. That’s all there was to it...except to say that if the money was not paid, the addressee would die. The letters were unsigned, except for an ink imprint of the caller’s hand (thus the term "black hand"). It never concerned the extortionists that the victim might be unable to pay; if they didn’t...well, they would serve well as posthumous warnings to anyone else refusing "Papa Black Hand".

Top extortionists like "Big Jim" Colosimo or "Diamond Joe" Esposito would use the gained funds for a number of purposes -- as bribe money to officials to look the other way while they ran their brothels and gaming houses openly, or merely to sustain their individual lavish lifestyles. Oddly enough, even though most of the Patch knew who the Black Handers were, no one fingered them. Not out of fear -- but social respect! The working class prey seemed to forgive Esposito and Colosimo because, in reverse nature, they were always there at Christmas and on other holidays religiosa to fund neighborhood soup kitchens and distribute presents to area children.

But, the threats, taunts, breaking of arms and murders continued year long. "Enforcers," the men who did the dirty work, emerged from among the rank and file of the Patch whose own families were promised immunity. The 42 Gang proudly supported Diamond Joe; thugs like "Needles" Gianola and "Fat Leonard" Caifano were some of the first in line with brass knuckles and stolen armament. Momo, too, found the hunt thrilling and the business lucrative. Without conscience, he quickly became one of the Padrone’s most reliable henchman.

The year 1920 brought a relief of sorts to Little Italy, for when the nation adopted the Prohibition Act, which forbade the manufacturing, distribution and consumption of alcohol, the Black Handers found another, easier way to earn a living. Because Americans demanded liquor despite the ridiculous law, the Underworld found a golden key by supplying that commodity. Certain whiskies were imported illegally from Canada, but much of it was homemade in breweries and distilleries assembled overnight across the nation. More than New York, more than Detroit, more than New Orleans, more than anywhere else, Chicago flourished.

One of the most enterprising bootleggers in the early 1920s was Diamond Joe, who brought from Sicily a regimen of top Mafioso muscle to oversee his operations. Among them were the five Genna brothers whom he charged with running a network of small basement distilleries throughout Little Italy. The community was given the equipment and the ingredients, and although the odors of cooking whiskey hung over the streets of the Patch night and day, the Irish cops who used to pummel the Italians now found the Genna’s bribe money quite satisfactory. It is estimated that the residences within Genna’s territory produced 300 gallons of rotgut whiskey per week. Awful stuff, but it served the purpose.

It was Momo’s job to collect the whiskey in tin drums and deliver it to a series of central warehouses around Chicago, from where it would be disbursed to customers’ homes and businesses. If a family failed to meet its weekly quota, Momo blackened an eye or busted a nose.

While Esposito had foreseen the value in Prohibition, and cashed in, Jim Colosimo on the South Side had decided his whores and gambling brought in more than he needed. His lieutenants like Johnny Torrio were unhappy watching the dollars slip through their hands while Esposito and the Gennas grew wealthier. In true gangland solution, Colosimo was found shot to death in the foyer of his famous Ristoranti on Wabash Avenue. Suddenly, Torrio became the man to watch. Making up for lost time, he wasted few moments to become overlord of not only the South Side but all of Chicago. He established a well-managed "business" of professional distilleries and breweries that stretched throughout the city and suburbs. He rounded up an army of "managers" to run the operations and divided his territory into "precincts" to be overseen by these men. Esposito claimed Little Italy.

Torrio also brought in Al Capone, a muscular and fearless gunsel he had known from his native Brooklyn. Capone became a trusted ally and served as a bodyguard and secretary for Torrio, maintaining his whores, bagging the revenue from his casinos, making sure the lawmen were well paid to ignore the channeling of whiskey and beer from one end of the city up the other, and eliminating any devil’s advocates. Under Big Al’s watchful eye, things ran smoothly.

It was in the Four Deuces, a dingy saloon and brothel off 22nd Street, that Momo met Al. He had heard of him and knew him immediately by his girth and the scar that marred his left cheek, a scar put there in a knife fight in New York. Momo ingratiated himself with Capone and it wasn’t long thereafter that Capone called on Momo to perform an important task.

Most history books state that Al and Torrio were inseparable. When Torrio was nearly killed outside his home in 1925 by a rival North Side Irish mob, and decided to quit Chicago, turning his operations over to Capone, it was supposedly with reluctant heart that Al accepted it. By all reports, he wept to see his beloved "Papa Johnny" leave. But, one surprising allegation emerges from the book Double Cross, written by his brother Chuck, and based on his conversations with Momo.  According to Chuck Giancana, Capone -- and not the rival gang -- had been behind the attempted Torrio assassination. Capone had grown ambitious and wanted the business for himself, claims Chuck Giancana

Momo had been the lead triggerman and although Torrio did not die, barely surviving his wounds, the results were what Al wanted: to rid himself of Torrio in a tidy way. The North Siders were blamed for the attack and Torrio, afraid of further wrath, had fled. Momo had done his job well.

That done, it was now time to eliminate other partners who had grown too politically strong and might prove roadblocks on Al’s path to total autonomy. Among these were Diamond Joe Esposito and the Gennas. Momo eradicated them for Al, one by one. To Capone’s amusement, Momo again shifted the blame to the North Side Irish.

Because of Momo’s "in" with the Big Guy, his prestige rose quickly. Others in the Outfit like Frank Nitti, Capone’s chief aide-de-camp, and "Machine Gun" Jack McGurn, top triggerman, called on him to annihilate opponents.

Momo, tired of roaming, had moved back in with his father. He demanded respect and commandeered his father’s home as his headquarters. (There would be no more beatings on the oak tree.) While his father, stepmother and striplings barely made do, Momo sported the latest fashions, drove the most expensive cars, ate at the most expensive restaurants, and, when he called a meeting with his partners in crime at the house, the rest of the family had to leave for the day.

The neighborhood respected its most successful son and out of fear and in pursuit of favors, fell over him as if he were royalty. They stepped aside when he strolled the streets of the Patch, whispering "there goes Capone’s boy," and offered him fruits, vegetables and items from their two-by-four shops. Now that Esposito was history, Momo was King of Little Italy. He settled local disputes for his cumpari, bumped off antagonists and kept the alderman and ward healers content and voting for corrupt officials like Mayor Bill Thompson at election time. He egotistically called himself "Justice of the Peace".

In 1929,  Jack McGurn was handed the task of finally eliminating Capone’s last rivals, the no-longer-useful but ever-interfering North Side gang now under the direction of George "Bugs" Moran.  The result was to be known as the St. Valentine's Day Massacre.  While no other source mentions Momo's participation in the massacre, Chuck Giancana claims in  Double Cross that Momo was asked to serve double duty as both driver and assassin. McGurn’s plan was to herd together the central members of the Moran faction into one place for wholesale slaughter. A McGurn ally promised a very large delivery of shanghaied whiskey to Moran at his warehouse on North Clark Street that day, providing Moran’s boys help unload the cache. The Irishman agreed. Once McGurn knew they had all assembled --seven of them total -- the plan went into effect. Dressed as policemen, the murderers, including Momo, stepped into the warehouse unquestioned. The North Siders relented to the annoying frisk and lined up grumbling against a wall. None of them anticipated what happened next. When they became conscious of the staccato of machine guns behind them, it was too late.

Again, Momo had served well. Of Momo, McGurn was supposed to have told Capone, "A good wheelman is hard to find, but a good wheelman with the smarts and guts to kill is a gold mine."

The opportunities of the Roaring Twenties had provided Momo Giancana with the stuff a gangster’s dreams are made of. And Momo took every advantage to heart and in hand. By pleasing the right people and by killing the right people, his life’s foundation was laid, his visions set in granite.