by Sam Giancana
Colosimo’s downfall began in 1918 when the United States Congress enacted the Volstead Act, outlawing the sales and consumption of all alcohol inside the country’s borders. Satisfied with a criminal regime built on prostitution, gambling, and extortion, Big Jim was reluctant to dip his organization’s beak into the business of bootlegging illegal liquor. This stance on America’s newest and most popular growing racket was very unpopular with his men—especially his nephew Johnny Torrio, who saw the prohibition of alcohol in the country as a huge cash crop just waiting to be properly cultivated.
Big Jim’s aversion to changing with the times would end up costing him his life. In May 1920, just days after returning from a European honeymoon he had taken with his 20-year-old bride, a dancer he had met at the club, Colosimo was gunned down while entering his office by assassins from New York City, who were acting under the order of none other than his nephew Johnny the Fox.
With his uncle out of the picture, Johnny Torrio took the reins of the Chicago underworld and jumped full force into the bootlegging industry, building his South Side-centered gang into one of the largest liquor cartels operating in the United States. Under Torrio’s command, the organization made a number of key alliances with other syndicates around the country and created a network of area bootlegging gangs, assigning each one its own territory in an attempt to cut down on violence.
This concept worked for a while, but soon the stability that existed among the various factions started to dissolve. The primary trouble began to fester around the later part of 1924 in suburban Chicago Heights, where each gang had most of their distilleries. Heated disputes over brewery expansion erupted, and lines were drawn in the sand; it was Torrio’s South Siders against a North Side gang led by Dion O’Bannion, a violence-prone Irish gangster who owned one of the city’s largest flower shops. O’Bannion’s lieutenants started intercepting Torrio’s product shipments and destroying his organization’s liquor-cutting plants. In retaliation, a murder contract was placed on O’Bannion’s head, and in the week leading up to Thanksgiving 1924, he was killed outside his flower shop by Torrio-dispatched gunmen, once again brought in from New York City.
Torrio’s rule atop the Chicago underworld would come to an end soon thereafter when, in January 1925, he was shot several times and brought to the brink of death on orders from Dion O’Bannion’s successor and new North Side boss, Earl “Hymie” Weiss. After his recovery, Torrio abdicated the throne to the city’s kingdom of crime to Al “Scarface” Capone, a twenty-six-year-old import from the East Coast, who would go on to become the most iconic organized crime figure in the nation’s history.
Born and bred in Brooklyn and mentored by notorious Coney Island mob boss, Francesco “Frankie Yale” Ioele, Capone moved to Chicago in the early 1920s and joined the Torrio gang. Getting his start as a bouncer at the legendary Four Deuces bar and brothel located in the city’s red light district, the man they called Scarface eventually worked his way up the organizational ladder until he was Johnny Torrio’s right-hand man and second in command.
Capone built Torrio’s already burgeoning empire into a colossus of riches. He ruled with an iron fist; filled the ranks of his crew with the city’s best young hoods (future Outfit leaders Anthony Accardo, Sam Giancana, and Joey Aiuppa among them), plucked from the area’s toughest youth gangs (like the Circus Gang and the 42 Gang); and indulged in a life of opulence few in the American gangland landscape had ever seen or experienced. And he did it all while courting the press, a strategy never previously employed in his line of work; thus Capone became the country’s first true media gangster, using newspapers and radio broadcasts to enhance and parlay his reputation to heights he could not have reached in his rule of the street alone. With the aid from a fast-growing and headline-happy mainstream media, Capone built a legacy as big as his bank account. Estimates place the Capone empire at reeling in close to $100 million a year, an astronomical feat at that time.
Even though Torrio was long gone from the Windy City—retiring to a homestead on Long Island—Capone continued to wage war with the North Side Irishmen, who steadfastly refused to get in line behind the South Sider’s and acquiesce to the territory restrictions put in place by Torrio at the beginning of the decade. Maintaining a vice grip on every area of the city except the North Side, Capone became obsessed with corralling it under his gang’s banner. After the murder of Hymie Weiss in October of 1926, the leadership of the Irish syndicate shifted to George “Bugs” Moran, a man who held little respect for his South Side foes and showed no deference to Capone. Moran had his lieutenants continue their assault on Capone’s liquor shipments and breweries, killing anyone who got in their way.
By early 1929, Capone had reached his boiling point and decided a mass execution of Moran and his men was the only way to win the treacherous street war and conquer the last portion of the city that he needed to complete a monopoly over the entire Chicago underworld. Arranging for his allies in Detroit’s infamous Purple Gang, an all-Jewish mob headed by the four Bernstein brothers, to set up a faux meeting on Valentine’s Day in a North Side garage under the premise of giving Moran’s gang a truckload of discounted illegal alcohol, Capone’s plan was to kill everyone present.
Dressed as policemen, Capone’s men stormed the garage, acting as if they were raiding the location, a well-known Moran gang headquarters. Lining up all seven of Moran’s men that were there, the South Side assassins machine-gunned each of them to a bloody death, leaving behind only a barking German shepherd to alert those outside of the blood-soaked carnage within. Luckily for Moran, he was late for the meeting that morning and escaped a gruesome fate. Following the massacre, Moran gave in and surrendered control of his territory to the Capone gang. Scarface finally had all of Chicago under his thumb.
The massive publicity the ghastly event garnered, dubbed by the press The St. Valentines Day Massacre, put a huge target on Capone’s back, and a law enforcement task force, named “The Untouchables,” was created for the sole purpose of bringing him to justice. Unable to nail the South Side crime lord on criminal charges, they went after his financial records and eventually convicted him for not paying his income taxes. Jailed in 1931, Al Capone turned over the keys of his organization to his first cousin and the gang’s unofficial business manager, Francis “Frank the Enforcer” Nitti. Capone would never rule the streets of Chicago again. Released from prison in 1939, his mind ravaged by syphilis, Capone retired to Florida before finally succumbing to the disease in 1947.
EVEN before Al Capone’s incarceration, the nation’s underworld was undergoing a major facelift. Following the conclusion of a prolonged gang war that played out in the streets of New York City, Charles “Lucky” Luciano found himself as the newly crowned king of the East Coast mob. Not wanting to assume complete and total control of the region’s crime syndicate for fear of meeting the violent and untimely deaths of his two predecessors, Luciano called for a meeting of all the country’s various mob bosses to lay out a proposal he created that would install a nationwide criminal combine. The conference of crime bosses was held at a hotel in Atlantic City and attended by over thirty mob heads of state. Luciano spoke of geographically designated “families,” ruled over by three-man administration teams, all of which would be overseen by a national board of directors, called “The Commission,” that would govern the entire entity and mediate disputes that arose between the twenty-six regional factions. He called his vision “La Cosa Nostra,” Italian for “this thing of ours”; after an unanimous vote, it became the new face of American organized crime. The modern-day mafia was born.
Although the boys from Chicago went along with Luciano’s vision at the conference, they tweaked the model a bit when applying it to themselves and their newly installed hierarchy. They adhered to the basic rules laid out by Luciano, but their application of those rules was significantly less stringent. For example, in the years to come, the position of consiglieri, in all other families the third person in charge, actual
ly held the most weight when it came to decision making. Where in most other families the power that could be achieved by non-Italians was capped, in The Outfit—a moniker adapted for the Chicago mafia in the late 1930s—non-Italians were able to hold very influential posts in the administration, even oversee full-fledged Italian members. This slight change from standard mob operating procedures consistently worked in favor of The Outfit, making it considerably more difficult for law enforcement to identify and take down the family’s real power brokers.
UNLIKE Capone, who took over an organization that was thriving, when Frank Nitti assumed command of the Chicago crime syndicate in 1932 it was stagnating. Capone’s legal woes and his departure from the city left a huge void and lingering questions regarding the vice conglomerate’s stability. And with the repeal of the Prohibition laws in 1933, the gang was perceived to be on the decline. Though undaunted by the prospect of breathing new life into the organization, Nitti faced an uphill battle in rebuilding and reshaping the legendary unit of Windy City outlaws.
Aided by the likes of veteran Capone gang members Jake “Greasy Thumb” Guzik, Murray “The Camel” Humphreys, and his own personal protégé Paul “The Waiter” Ricca, Nitti focused his attention on expanding his new crime family’s reach into labor racketeering, local politics, gambling, and loan-sharking as a means of bringing in the money lost due to the re-legalization of alcohol. Guzik, a Jew and the syndicate’s point man in city hall, spearheaded the infiltration of the local labor unions, Humphreys, spawning from Welsh descent, headed the takeover of all illegal gambling being run in the area. Ricca, with the aid of Capone’s former bodyguards, Tony Accardo and Phillip “Dandy Phil” D’Andrea, took the responsibility of getting in line all of the loan-sharking operations taking place within the city limits.
Nitti’s strategy paid quick dividends, and by 1935, the organization was back to equaling its profits from the heyday of Prohibition. And because he went out of his way to stay out of the spotlight—a big contrast to the days of Scarface Capone—Frank the Enforcer was poised for maximum growth in the future.
His ten plus years at The Outfit’s helm came to an end in March 1943, when Nitti committed suicide, after being indicted in a wide-reaching ploy by the Chicago mafia to extort money from a number of Hollywood movie studios and having been diagnosed with terminal cancer. Replacing Nitti, at least for the short term, was his underboss and protégé, Ricca. The Waiter, originally named Felix De Lucia, came to the United States in 1920 from Italy, on the run from the law on murder charges. Indicted in the same Hollywood extortion case as his former boss, Ricca was sent to prison in 1944. As he headed to prison, he tapped his best friend and the family’s primary enforcer, Tony Accardo—nicknamed “Joe Batters” by Capone for his skill at using a baseball bat as an enforcement tool—to run The Outfit in his stead. It would be a role Accardo would keep one way or the other until he died almost fifty years later, having never spent a day in jail.
Under Accardo, The Outfit continued to flourish. An innovative leader, he was not one to rest on his or the syndicate’s laurels and became intent on expanding the family into new and profitable horizons whenever an opportunity presented itself. The first thing he did was reemphasize the street tax—extorting tribute payments from any and all illegal businesses being conducted in the city; Frank Nitti employed this at the onset of his reign in the 1930s but extortion had not been actively enforced over the preceding years. Also known as “The Big Tuna,” for his love of fishing, Accardo made certain everyone in Chicago knew that The Outfit was the only ball game in town, and that the day of independent vice merchants operating without cutting them in for a piece of their rackets were now over. Then he set his sights on staging a takeover of the local wire services, businesses that provided horse racing and professional sports’ results to the area’s bookmakers. Joe Batters didn’t want any middlemen cutting into his organization’s profit margins. The last of the independent wire operators, James Ragen—someone who scoffed at the notion of giving into Accardo’s strong arm tactics—was killed in June 1946, and The Outfit’s acquisition was complete.
As the end of the decade dawned, Accardo, firmly entrenched in the boss’ chair and his syndicate running at its highest level ever, remained on the lookout for even more gangland avenues to exploit to his advantage. In the most daring move of his career, he decided to muscle in on the city’s traditionally African American policy lottery, better known as the numbers racket. Centered in the all-black South Side ghettos, policy was a cash cow participated in by over 80 percent of the residents in the rundown housing projects that dotted the neighborhood.
The idea to go after the lucrative numbers business was actually not Accardo’s. His close confidant and childhood pal Sam Giancana, recently sprang from prison, hatched the plan while being housed with several black policy leaders. One of them was Edward “Eddie the King” Jones, who Giancana became friendly with in jail and who explained to him how the racket worked. Within days of gaining his freedom, he met with The Big Tuna and laid out his idea. Accardo fell in love with Giancana’s scheme and tapped him to oversee its application, knowing it would not be an easy task to accomplish. It wasn’t.
A percentage of the South Side crime lords refused to give in to the mafia without a fight. The flames of war raged between The Outfit and the black numbers czars well into the early portion of the 1950s, with both sides suffering casualties.
The mob’s most ardent adversary was Theodore “Tough Teddy” Roe, a vicious crime lord who would not budge at The Outfit’s demands and was unafraid of using violence against the Italians to protect what he saw as his rightful turf. When Giancana sent his brother, Chuck, and his bodyguard, Leonard “Fat Lenny” Caifano, to try to negotiate with Roe, he shot Caifano to death. At that point, Accardo and Giancana pulled out all the stops and designated all their possible resources into killing Teddy Roe. They finally did in August 1952, and, with his demise, officially took over the South Side and its policy operation.
Next, Accardo, with counsel from trusted boardroom lieutenants Murray Humphreys and Gus “Slim” Alex, made the move to expand The Outfit’s gambling interests outside of Chicago and into the vice hotbeds of Las Vegas and Havana, Cuba. Using the mob’s access to the Teamsters Union pension fund to help finance the building of the Vegas Strip and his personal influence in political and East Coast mafia circles to infiltrate Havana, the Windy City don had now taken his crime family international. By the late 1950s, he was arguably the most powerful mob boss in the entire country. But instead of seeking to bask in the overwhelming glow of his incredible exploits, he made a decision that shocked a great deal of people, both inside the underworld and out—he sought to get out of the game all together.
KNOWING the heat from law enforcement was building against him and knowing that if he remained don he would most likely end up in prison, Accardo wanted to retire. Paul Ricca, now a free man, semiretired, and acting as Accardo’s top counselor on family affairs, advised him against an all-out departure from the syndicate. Instead, Ricca theorized Accardo should move into the role of consiglieri, name a front boss, and pull the strings from behind the scenes, safely removed from the mob’s day-to-day affairs and the police scrutiny that goes with it. Buoyed from his directing the successful takeover of the city’s numbers business only a few years earlier, Giancana, nicknamed “Mooney” or “Momo” for his often gutsy and sometimes crazy behavior, was the logical choice to take Accardo’s place atop The Outfit food chain. Holding the post for nine years, Giancana ushered in an era of excess that harkened back to the days of Capone.
Like the venerable Scarface himself, Giancana craved media attention and exploited the ability his new status as boss gave him to live as lavish a life as possible. He courted Hollywood femme fatales; cemented friendships with celebrities, most notably Frank Sinatra; and even dabbled in big-time politics, allegedly helping the Kennedy family rig the 1960 presidential election and helping the CIA in a plot to kill Cuban
dictator Fidel Castro. While Accardo remained comfortably in the shadows, Giancana flaunted his mob credentials at every opportunity. And the press ate it up, making him world famous. Accardo, on the other hand, began to tire of his longtime friend’s attention-grabbing routine and in 1966, with the support of several other Outfit elders, had him deposed.
Unhappy with his treatment in Chicago, Giancana fled the country for Mexico. While in exile, he established numerous overseas gambling ventures that made him even wealthier than he was when he was a don. A bearded Giancana ended up back in the Windy City in 1974, only to be killed shortly thereafter by his former mafia partners for intending to testify in front of a Senate committee investigating the Castro assassination plot and for not sharing profits from the gambling operations he ran while out of the country.
BETWEEN 1966 and 1970, The Outfit would go through three bosses, all while Accardo sat in the background silently directing family affairs from his slot as consiglieri, living half the year in Chicago and the other half in Palm Springs, California. First, Accardo chose Sam “Teetz” Bataglia, a West Side crew chief who made his name on the streets as a feared enforcer, to take the reins. When Battaglia was sent to prison, he appointed Felix “Milwaukee Phil” Alderesio, the head of The Outfit’s enforcement unit, as the new boss. After the government nailed Alderesio on charges of trying to defraud a local bank, Accardo called on his former driver and ace protégé John “Jackie the Lackey” Cerone to take over as don. But he too was soon removed from life as a free man, convicted on a charge of transportation of stolen goods across state lines when one of his lieutenants, Lou Bombacino, flipped and testified against him in court.