Before his fall, the man who would one day rule Chicago’s underworld had already learned the value of silence. When a congressional committee pressed him in the 1950s about whether he disposed of opponents by stuffing them into trunks, he answered with a simple refusal. His reply, he said, might tend to incriminate him. Asked again whether he would tell them anything about his operations, he giggled before repeating the same answer.
A senator remarked that only little girls giggled. Sam Giancana, known to his friends as Mooney, said nothing more. By the 1960s, Giancana stood as a titan of Chicago’s criminal empire, commanding the notorious outfit with absolute authority. His reach extended deep into legitimate businesses and political circles, drawing both admiration and fear.
Allegations swirled around him: covert operations, political intrigue, and even suspected involvement in a plot against President John F. Kennedy alongside Santo Trafficante. His life was a labyrinth of danger and mystery, and the road that carried him to that pinnacle ran through more than two decades of violence, betrayal, and relentless ambition. In the aftermath of the St.
Valentine’s Day Massacre, Al Capone was convicted of income tax evasion on October 17, 1931, and sentenced a week later to eleven years in federal prison. Frank Nitti, Capone’s enforcer, took over the public face of the organization. But Giancana’s own turn was quieter. Released from prison on Christmas Eve 1932, he married twenty-three-year-old Angeline Toal on September 23, 1933.
By June 1935, the couple had their first child. To satisfy his probation officers, Giancana took a job at his brother-in-law’s factory earning forty dollars a week. In reality, he often helped Murray Humphries, the gang’s shrewd Welshman, with labor issues that required persuasion. From 1934 to 1935, he occasionally drove for Jack McGurn, benefiting from the women McGurn introduced him to.
By 1936, however, McGurn had lost favor, and Mooney carefully avoided showing support for him in front of Paul Ricca. When McGurn was killed on February 13, 1936, nobody mourned his loss. Mooney had developed a deep admiration for forty-five-year-old Paul Ricca, a man who had arrived in New York around his twenty-first birthday. Ricca worked for Diamond Joe Esposito in Chicago alongside the Genna brothers, running moonshine and serving as a waiter at Esposito’s Bella Napoli, where he earned the nickname Paul the Waiter.
He climbed quickly, winning Esposito’s favor and becoming closely aligned with Al Capone. According to Giancana, the media might proclaim Frank Nitti Chicago’s new boss, but that was a ruse. Those on the inside knew better. Paul Ricca ran the show while Nitti took the public-facing role, drawing attention from the press.
Ricca operated behind the scenes alongside Murray Humphries, using money as the enforcer. What started as extortion, squeezing businessmen for labor peace, evolved into a lucrative enterprise. They targeted unions for control, enlisting Willie Bioff and Johnny Roselli to lead groups of thugs for intimidation. In 1934, the Chicago gang expanded into Hollywood after backing Joe Kennedy’s entry into the film industry.
They went national, placing George Browne and Willie Bioff in key positions within the stage employees’ union, securing Chicago’s control over Hollywood and its theaters. With lax regulations on union funds, the syndicate gained immense wealth and power. By 1936, all major unions in Chicago were under their control. By 1937, it was widely known in Chicago’s underworld that Ricca had substantial influence over local, county, and state politicians.
His supporters claimed he even had access to the White House. The syndicate had matured into a formidable organization, consolidating control over various industries. Giancana’s own journey took a new turn as he revealed talents beyond driving and enforcement. His knack for numbers became valuable.
His focus shifted to collecting protection money from patch shop owners, building his own little group of racketeers. By 1937, he had established his empire in the Patch, delving into car thefts, burglaries, moonshining, and other illegal activities. His association with the syndicate granted him immense power, enabling him to provide jobs or take them away at will. Impressed by his capabilities, Ricca and Humphries saw him as astute and calculating.
Mooney, in turn, admired their leadership, having witnessed how they orchestrated political maneuvers and even intervened to save Joe Kennedy from a contract on his life. As Prohibition ended, the syndicate diversified. Mooney became involved in various profitable ventures, expanding union rackets. The syndicate focused on selling alcohol legally, rebranding and marketing it as premium or imported.
Much of Joe Kennedy’s high-quality Scotch was actually rebranded syndicate alcohol. In the summer of 1937, Mooney tasked Guido Genely with establishing a moonshine operation in Garden Prairie, Illinois. By January 1938, they were producing enough alcohol to supply connections along the East Coast, turning a significant profit. Their success was short-lived.
In January 1939, treasury agents raided the still, arresting Mooney and his cohorts. In May, he changed his plea to guilty, was convicted on nine counts, and received a four-year sentence with hefty fines. While Humphries expressed intentions to study English and geometry in prison, Mooney embarked on an unexpected path. Released before Christmas 1942 on early parole, Mooney met Eddie Jones, boss of the numbers racket in Chicago.
Jones told him he ran the biggest of thirty policy games in the city. Mooney brought the idea of taking over the black policy games to Paul Ricca, but Ricca and Tony Accardo were caught up in a federal indictment, the Bioff case. Three years earlier, federal agencies had investigated the stage employees’ union, uncovering significant corruption. Bioff and George Browne were convicted of labor racketeering.
Another accomplice, producer Joe Schenck, who Mooney claimed had funneled over half a million dollars to Roosevelt’s campaign for the syndicate through Postmaster General Farley, was imprisoned for tax evasion. Chicago maintained its Hollywood operations following Bioff’s conviction, with Johnny Roselli taking charge. Bioff’s testimony threatened to expose the highest levels of the syndicate. Surprisingly, Mooney appeared pleased about the potential fallout, having received approval that winter to expand his gambling operations, especially into the policy rackets.
He wasted no time. He structured his territory based on race and city wards: the colored section for policy, the white neighborhoods for traditional gambling. He appointed Fat Leonard Giannola to manage the expansion. Under Mooney’s guidance, Fat Leonard set up bookmaking joints in legitimate taverns and restaurants, many offering back rooms for poker.
Competitors were given a simple choice: join forces with Mooney or face serious consequences. After dealing with a few who resisted, others quickly fell in line. Before long, Mooney controlled around two hundred operations in Chicago and another two dozen in the county, each generating an average of two thousand dollars per month. The colored policy rackets proved more challenging.
Progress was slow until Eddie Jones, upon his release, offered his support. Colored gamblers were hesitant to participate in operations run by whites, and few policy men were willing to collaborate with the aggressive Italians. In March 1943, news of indictments against Paul Ricca, Frank Nitti, and several others shook the underworld. Ricca instructed Nitti to take the fall, but Nitti chose suicide instead.
Following a ten-year prison sentence for Ricca, Tony Accardo became the new boss, with Humphries and Guzik as advisors. Mooney recognized this as his chance and quickly worked to strengthen his position. As the war intensified in the spring of 1943, Americans faced stricter rationing measures. Mooney seized the opportunity to profit by hustling stolen ration coupons.
He then decided to assert his dominance by kidnapping Jake Guzik in April. After holding him hostage for two days with a gun to his head, Mooney offered a choice: accept the money and support Mooney, or face a bullet. Guzik wisely chose to support him. By 1946, Mooney had become underboss to Tony Accardo, a position earned through the success of his gambling operations and his network of associates.
He traveled frequently to Florida, California, Cuba, and New York. In May 1946, he orchestrated the kidnapping of Eddie Jones, giving him a similar choice as Guzik three years earlier. Jones needed no convincing. Before his release, he produced $250,000 in unmarked ransom money and agreed to surrender his entire operation.
Two weeks later, Jones and his family departed for Mexico. Teddy Roe, a rival, boldly proclaimed he would sooner die than let the Italians take over his operations. No attempts were made on his life that summer. Instead, Mooney leveraged his political and police connections to intensify pressure, eventually forcing Roe to shut down.
By August, apart from Roe’s operations, Mooney had gained complete dominance over the policy rackets. Meanwhile, Accardo tasked Guzik and Humphries with expanding into the national gambling scene, targeting states like Iowa, Kansas, Indiana, and Michigan. They aimed to establish operations in Dallas, Texas, and finalized the takeover of Continental Press, a wire service in Cleveland. Despite their efforts, the Dallas sheriff declined a $150,000 bribe and exposed their plans, leading to bribery charges and a setback.
Mooney had another card: Jack Ruby, who was to open a seedy night spot that would help the syndicate bypass the sheriff. In December 1946, Lucky Luciano convened a meeting of the commission in Havana, assembling the thirty-six most prominent mob leaders in the country. Mooney’s presence affirmed his acceptance into the syndicate and recognized his position within the Chicago hierarchy. In March 1951, Mooney faced scrutiny from the IRS and was indicted on sixty-seven counts of gambling.
Around this time, he encountered his old rival Teddy Roe once more. On June 19, 1951, an ambush on Roe failed, resulting in the death of Mooney’s associate Leonard Giannola. On August 4, 1952, Roe was shot and killed, allegedly on Mooney’s orders. Mooney never faced trial on the indictments.
On April 10, 1954, Mooney’s wife suffered a cerebral embolism and died. By the middle of 1955, Tony Accardo and Paul Ricca were under scrutiny from the IRS. Accardo felt especially nervous and eager to disappear from public view, much like how the Bioff scandal had opened Mooney’s path to power over a decade earlier. The pressure on Accardo and Ricca provided the final push.
Accardo stepped aside, and during a private gathering at the Armory Country Club in North Chicago, Sam Giancana was officially named the boss of the Chicago outfit.