Chicago had never seen a young criminal quite like Sam “Momo” Giancana. By the age of thirteen, in 1921, he had earned the nickname “Mooney” because he was considered the wildest and most reckless of them all. He was a natural behind the wheel, famous for taking corners at full speed on two wheels, a dangerous escape maneuver that made him a legend in the Patch, the Little Italy neighborhood where he had grown up. But long before he became one of the most powerful mob bosses in America, before his alleged ties to presidents and his rumored role in the plot to kill Fidel Castro, Giancana was just a hungry, homeless boy running with a gang of teenage thieves.
Born on May 24, 1908, and baptized Momo Jimmy Salvatore Giancana, he was the son of Antonio and Antonia Giancana, immigrants from the Sicilian village of Castelvetrano. The family lived in the Patch, a stretch of Little Italy between Taylor and Mather streets that had once been dominated by Chinese immigrants. Between 1890 and 1910, the Italian population of Chicago swelled to more than forty thousand, creating intense friction with the Irish and Jewish communities. Crossing into the Irish neighborhoods along Halsted Street meant risking violence.
The Italians viewed the Irish-run police as an enemy that offered no sympathy, and they responded by clinging to their own kind and their own cultural traditions. It was a world that mirrored the old feudal order of Sicily, where armed men imposed laws arbitrarily and nobody trusted the authorities. Antonio Giancana looked at his son differently than he looked at his daughter Lena. He saw Mooney’s independence as rebellion.
When the boy’s mother died of a miscarriage in 1910, Mooney was barely two years old, but those around him noticed a marked change in his behavior. Antonio quickly remarried a serious woman named Mary Leonardy, who gave him two more children, Antoinette and Mary. His strict discipline, including physical punishment, was meant to control the boy, but it only fueled his defiance. By the age of ten, Mooney was labeled a delinquent and spent six months in the St.
Charles reformatory. When he returned home in 1918, he found a family under strain, crowded and struggling. He began sleeping in abandoned cars and wandering the streets until, in 1920, he found a place where he finally belonged: the 42ers. The gang, initially led by Joey Colloway, also known as “Babe Ruth,” was made up of bold young Italian men from the Patch.
They started with small thefts like stealing clothing and progressed to stealing cars. Over time, their activities escalated to bombings and murder, earning them a reputation as the most ruthless Italian gang in the area. They probably took their name from Ali Baba and the Forty Thieves, even though the gang never had more than about twenty members because of deaths and prison sentences. But their small numbers did not matter.
They were feared and respected in the Patch. The residents admired their ability to outwit the Irish police, whom they distrusted, and saw in the gang a familiar kind of law and order from the old country. Outside the neighborhood, the 42ers gained fame for their daring escapes and reckless leadership, often making headlines for their risky two-wheel cornering. Mooney, the homeless and hungry boy, joined this unusual group and trained himself to be the best driver among them.
Avoiding capture was essential, and the gang needed money to bribe the police if they were caught. The leader collected ten dollars a month from each member for that purpose. Mooney quickly understood that the police were not interested in justice; they were interested in money. If a cop or a judge could not be bought, they simply had not found him yet.
The usual price to drop charges was five hundred dollars, which was beyond what the young gang members could afford. They had to go to their fathers, who, despite their own financial struggles, could not abandon their sons and paid the police to keep them out of trouble. The young men looked up to famous mob figures like the sugar baron Diamond Joe Esposito, the young Al Capone and his associates, Big Jim Colosimo, and his nephew Johnny Torio. In the early twentieth century, Chicago’s underworld was crowded with varieties of gangs.
The Irish gangs, like the Market Street and Valley gangs, were led by figures such as Charles “Dino” Panian, who ran the Little Hellions and focused on robbery and pickpocketing. The Italian gangs, led by Esposito and Colosimo, used tactics like extortion and bribery to gain influence. Esposito focused on building political and union connections, while Colosimo took a different path, establishing high-class brothels that made him rich and powerful. By 1909, Big Jim Colosimo was facing challenges from the same rival gangs that threatened Diamond Joe Esposito, and he asked for help.
The request required additional organizational strength, and Esposito was inspired to bring Colosimo’s nephew Johnny Torio from New York. Torio, known for his leadership skills, ran Colosimo’s operations efficiently, including the brothels. In 1910, to strengthen his territorial control, Esposito brought the six Genna brothers, known as the “Terrible Gennas,” with the help of Joe Fusco. The Gennas quickly established themselves as enforcers, extortionists, and brothel operators under Esposito’s protection.
Neighborhood gangs like the 42ers provided a steady pool of recruits for leaders like Diamond Joe Esposito. Businessmen also recognized the value of gang tactics, often hiring gang members to protect their interests or influence potential clients. In 1919, Johnny Torio recruited Al Capone from the Five Points gang in New York to help expand Colosimo’s empire in Chicago. Torio hoped to persuade Big Jim Colosimo to shift his focus from prostitution to illegal liquor, but Colosimo resisted and refused.
Frustrated, Torio ordered his uncle eliminated, and Colosimo was murdered in May 1920. Chicago’s gangs occasionally tried to cooperate, but greed, betrayal, and ethnic tensions ignited a full-scale territorial war. During this chaotic period, Esposito exercised unchallenged authority in the underworld. His gang controlled the distribution of sugar from Cuba, a vital ingredient for alcohol production during Prohibition.
His alleged license from President Calvin Coolidge in 1923 gave him a neutral status, allowing him to rise above daily gang conflicts and influence criminal and official policy across the country. By 1923, when Mooney was fifteen, he was working for Esposito, smuggling sugar and alcohol. Esposito employed the Genna brothers to oversee the region’s distilling operations, managing hundreds of stills and producing alcohol worth more than a million dollars a year. Italian immigrants in the area were paid generously for their participation, which ensured their loyalty.
Esposito’s dominance even extended to exploiting young brides, demanding to spend their wedding nights with them before their husbands, though many harbored thoughts of killing him. Still, his rule went unchallenged for twenty years, marked by his foul behavior and brutal control of the Chicago underworld. By the end of 1924, Diamond Joe Esposito was the most powerful man in Chicago, and perhaps all of North America, with close ties to figures like Al Capone and Johnny Torio. Although he preferred neutrality, his Italian heritage forced him to support Torio and Capone, creating a formidable alliance against rivals, or so he thought.
Tensions escalated within the Torio and Capone gang over the distribution of wealth, particularly between Capone and Torio. With support from Ricker and Humphrey, Capone orchestrated Torio’s retirement in 1925, using strong young men like Mooney and Leonard “Needles” Gianola to deliver the message. After Torio’s retirement, Capone’s forces targeted the Genna brothers, eliminating them. Angelo Genna was killed in a car ambush, and his brother Mike was captured and fatally wounded in a shootout with police.
Tony Genna, the last remaining obstacle, was tracked down and killed by Capone’s men, including Mooney and Gianola. According to more contemporary accounts, Capone survived an ambush in January 1925, and twelve days later Torio was ambushed outside his home and left seriously wounded. Torio then retired, handing control of the gang to Capone and fleeing to New York. Another account attributes the deaths of Angelo and Tony Genna to the North Side gang, the same men who ambushed Torio.
Mooney rose within the 42ers by informing the police about Colloway, who was later shot dead, which strengthened the 42ers’ position as a de facto arm of the Chicago gang. In July 1925, Mooney’s life took a turn when he and Joey Sifer and Dominic Caruso decided to rob an upscale dress shop on the North Side. Although they stole more than fifty dresses, police officers on patrol thwarted their escape, leading to a chase. Mooney showed off his driving skills but lost control of the car, resulting in the capture of Caruso and Sifer, who confessed under interrogation.
The next morning, Mooney was arrested and charged with burglary, with bail set at five hundred dollars. His father arranged the money from Diamond Joe Esposito to secure his release. In September 1925, at seventeen, Mooney was arrested and convicted of auto theft, sentenced to thirty days in Joliet prison. In mid-September 1926, Mooney and two others attempted a robbery in the Levee district that resulted in the murder of a shopkeeper.
They were charged with robbery and murder, with bail set at twenty-five thousand dollars. Antonio again secured money from Esposito to free Mooney. Although acquitted of the dress shop burglary, Mooney’s days were darkened by the upcoming murder trial. As the trial approached, Mooney waged an intimidation campaign against the witness Alex Birber, resorted to bribery, and eventually ordered Rico to kill Birber.
With no witnesses, the case was dropped. Afterwards, Mooney focused on rising in the underworld. The next time the Capone gang summoned Sam Giancana, he received a message bearing his great betrayal. They told Diamond Joe Esposito to leave town or be killed.
On March 21, 1928, Esposito was shot and killed in a drive-by shooting while returning home with two friends. On February 14, 1929, Mooney and his friend Needles were picked up by police for questioning. Mooney was one of the first to be taken downtown, but he was released shortly after. At home, he was reading the newspaper with visible pleasure.
The front page showed horrific images of what Chicago was calling the worst gang massacre in history: the St. Valentine’s Day Massacre. It arranged everything in Capone’s favor and cemented his position as the undisputed boss of Chicago. Despite his high standing, Sam Mooney Giancana was sentenced to three to five years in Joliet prison for burglary.
As Sam Giancana’s influence grew within the Chicago gang, so did his involvement with the American government. But when the CIA contacted him to play a pivotal role in a secret mission to assassinate Fidel Castro, Sam found himself in a precarious position. The same government that once turned to him for help had now turned against him.