From Nitti Through Accardo
After Capone was jailed for tax evasion, his hand-picked successor, Frank Nitti, a former barber and small-time jewel thief, only nominally assumed power. In truth, power was seized by Nitti's underboss, Paul Ricca, who was acknowledged as "boss" by the leaders of the growing National Crime Syndicate. Ricca would rule the Outfit, either in name or in fact, for the next 12 years.
Over the next decade, The Outfit moved into labor racketeering, gambling, and loan sharking. Geographically, this was the period when Outfit muscle extended its tendrils to Milwaukee and Madison, Wisconsin, Kansas City, and especially to Hollywood and other California cities, where The Outfit's extortion of labor unions gave it leverage over the motion picture industry.
In 1943, the Outfit was caught red-handed shaking down the Hollywood movie industry. Ricca wanted Nitti to take the fall. However, Nitti had found, years earlier while in jail for 18 months (for tax evasion), that he was claustrophobic, and he decided to end his life rather than face more imprisonment for extorting Hollywood. Ricca then became the boss in name as well as in fact, with enforcement chief Tony Accardo as underboss. Around this time, the Outfit began bringing in members of the Forty-Two Gang, a notoriously violent youth gang. Among them were Sam "Momo" Giancana, Sam "Mad Sam" DeStefano, Felix "Milwaukee Phil" Alderisio and Fiore "Fifi" Buccieri.
However, later in 1943, following the "Hollywood Scandal" trial, Ricca was sent to prison for his part in The Outfit plot to control Hollywood. He, along with a number of other mobsters, was sentenced to 10 years in prison. Through the "magic" of political connections, the whole group of Outfit mobsters was released after three years, largely due to the efforts of Outfit "fixer" Murray "The Camel" Humphreys. As a condition of his parole, Ricca could not associate with mobsters. Accardo nominally took power as boss, but actually shared power with Ricca, who continued behind the scenes as a senior consultant.
Accardo joined Ricca in semi-retirement in 1957. From then on, Ricca and Accardo allowed several others, such as Giancana, Alderisio, Joey Aiuppa, William "Willie Potatoes" Daddano and Jackie "the Lackey" Cerone to serve as front men over the years, this due to some "heat" that Accardo was originally getting from the IRS, in the 1950s. Most of the front bosses originated from the Forty-Two Gang. However, no major business transactions, and certainly no "hits," took place without Ricca and Accardo's knowledge and approval. By staying behind the scenes, Ricca and Accardo lasted far longer than Capone. Ricca died in 1972, leaving Accardo as the sole power behind the throne.
The Outfit reached the height of its power in the 1960s. With the aid of Meyer Lansky, Accardo used the Teamsters pension fund to engage in massive money laundering through the Outfit's casinos, aided by the likes of Sidney Korshak and Jimmy Hoffa. The 1970s and 1980s were a hard time for the Outfit, as law enforcement continued to penetrate the organization, spurred by poll-watching politicians. Off-track betting reduced bookmaking profits and illicit casinos withered under competition from legitimate casinos. Replacement activities like auto theft and professional sports betting did not replace the lost profits.
Operation PENDORF (codenamed for penetrate Allen Dorfman) and the "Strawman" case ended the Outfit's skimming and control of their Las Vegas casinos. These events are fictionalized in the film Casino.
Operation GAMBAT proved to be a crippling blow to the Outfit's tight grip on the Chicago Political Machine. Pat Marcy, a made man in the Outfit, ran the city's First Ward which represented most of downtown Chicago. With the help of Alderman Fred Roti and Democratic Committeeman John D'Arco Sr., close Outfit associates, Marcy and company controlled the circuit courts from the 1950s until the late 1980s. Together, the First Ward fixed cases involving everything from minor traffic violations to murder. Attorney and First Ward associate, Robert Cooley, was one of the attorneys that represented many mafiosi and associates in which cases were fixed. As a trusted man within the First Ward, Cooley was approached and asked to take out a city police officer. Cooley, who was also an addicted gambler and in debt to certain undesirables, approached the U.S. Justice Department’s Organized Crime Strike Force, declaring he wanted to "destroy Marcy and the First Ward." Cooley was soon in touch with the FBI and began cooperating as a federal informant. Through the years, Cooley kept close with Marcy and the big shots of the First Ward. He wore a wire, recording valuable conversations at the notorious "First Ward Table", located at "Counselor's Row" across the street from Chicago City Hall. The results in Operation Gambat (Gambling Attorney) were convictions of 24 corrupt judges, lawyers and cops.
Accardo died in 1992. In a measure of how successfully he'd managed to stay out of the limelight, he never spent a day in jail (or only spent one day, depending on the source) despite an arrest record dating to 1922. Compared to how organized crime leadership transitions take place in New York City, Chicago's transition from Accardo to the next generation of Outfit bosses has been more of an administrative change than a power struggle.