“Three can keep a secret, if two are dead.” - Carlos Marcello.
Chicago Mobster Sam Giancana and his colorful and itinerant deputy Johnny Roselli sit atop an empire which controls unions, bribery, extortion, gambling, money-laundering, prostitution, racketeering and loan-sharking that envelopes most of the country, and includes the emerging casinos in Las Vegas and an especially lucrative partnership with the corrupt Batista regime in Cuba, in collaboration with soft-spoken Florida Godfather Santo Trafficante, Trafficante's close ally the brutal and savvy New Orleans kingpin Carlos Marcello, lecherous L.A. Don Jack Dragna, and the New York governing hierarchy, overseen by exiled Commission President Lucky Luciano and his wise and wiley Vizier, Meyer Lansky, who for all intents and purposes is the true Boss of Bosses. The mob enjoy free reign due to compromising and incriminating photos Lansky possesses of FBI Director J. Edgar Hoover, who insists time and again that organized crime does not exist in America.
When Castro storms to power in 1959, the mob's assets and properties in Havana are seized, and the gangsters are imprisoned or expelled, resulting in losses of millions. Trafficante and his consigliere Frank Ragano spend months in a Cuban detention center, and narrowly escape with their lives. The various Mafia chieftains are contacted by Robert Maheu and Sheffield Edwards, agents of the CIA, who suggest forging an alliance with the goal of assassinating Castro and returning Cuba to it's former state. True patriots, and seeing an opportunity to gain some leverage on the government, Giancana, Roselli, and Trafficante accept sizable payments from the agency, and numerous scenarios are planned (some quite outlandish), but the mission is eventually abandoned by the wiseguys due to unease about Robert Kennedy's duplicitousness and Trafficante's own continued secret dealings in Cuba.
Though Marcello and International Brotherhood of Teamsters President Jimmy Hoffa are justifiably distrustful of the Kennedys, Giancana is persuaded to fix the 1960 Presidential election in Jack Kennedy's favor by Frank Sinatra and due to assurances from Joe Kennedy that the mob would be left alone by their administration. After their service, Giancana and his associates are then double-crossed by the Kennedy brothers, who launch a major law-enforcement offensive aimed most directly at Marcello, Trafficante, and Giancana.
Public investigations take place, hearings are held (in which the bosses defiantly stonewall), numerous arrests are made, and business is continuously interrupted. Hoffa is repeatedly harassed and brought up on charges, and Marcello is apprehended and forcibly deported to Guatemala where he spends several weeks journeying through the jungle before figuring out how to a re-enter the states with Ragano's help. Deciding to take up arms, and using inside information obtained from their brief partnership with the CIA, the many government and law-enforcement members on their payroll and from Giancana and JFK's shared mistress and courier Judy Campbell, as an insurance policy against any formal investigation to take place after the fact, Marcello and Trafficante are able to utilize their southern base of power to organize a hit on the President with key assistance from Giancana's Chicago Outfit and Marcello's man in Dallas, Joe Civello. Hoover, having his own troubles with the Kennedys, looks the other way.
They are successful, and the heat dies down, but not for long. A number of ambitious politicians are looking to make names for themselves, and find organized crime to be a major headline-grabber. Giancana is made an example of by the press and by law-enforcement agencies who hound him and shadow his every movement. Giancana and Roselli both cultivate high-profile lifestyles and keep company with famous entertainers (Giancana's moll being singer Phyllis McGuire, and Roselli receiving producing credits on Hollywood motion pictures). Vegas becomes increasingly problematic, as a perfect storm of widely publicized murders, an influx of corporate ownership, and added regulations decimate what was once the jewel in the syndicate's crown. Spending much of the sixties in and out of courtrooms and having lost influence in Chicago and nationally due to his mistaken support for Kennedy, Giancana is forced out of his central position by Murray Humphreys, the combination's long-time fixer, and his mentors Paul Ricca and Tony Accardo, low-key old-timers who are the Windy City's unseen power and final word, and he spends the next few years running gambling establishments in Mexico.
Hoffa becomes much harder for the Mafia to keep a handle on, and Marcello is tried for and convicted of conspiracy and assault and is sentenced to prison, where he begins to lose control of his mental capabilities. His territorial hold is challenged by Trafficante, who with his right hand man Jimmy Longo is slowly and quietly consolidating power in the region and looking to tie up loose ends. Giancana and Roselli begin to turn on one another and suspect each another of imminent betrayal, and as Giancana's attempts to reassert himself on the scene are squashed by Accardo and his situation becomes increasingly desperate he becomes more malleable and willing to cooperate with authorities. When a Senate committee investigating CIA and Cosa Nostra collusion summons Giancana and Roselli to testify, Trafficante and his agency contacts decide that for the survival of the organization, and for reasons of national security, both men must be silenced.
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