'When everyone is dead, the Great Game is finished. Not before,' - Rudyard Kipling, author of Kim, (1901), considered the first modern spy novel.
At a closed-door Congressional hearing in June 1975, gangster Johnny Roselli testified about his role as a 'patriotic' assassin for the Central Intelligence Agency, a top-secret operation full of spies, sex, and unresolved mystery.
With wavy hair and steely blue eyes, Roselli looked like a successful businessman - a 'strategist' as he preferred to be called - or more like the Hollywood B-movie producer he once was.
No run-of-the-mill hoodlum, he wore dark designer sunglasses, dressed in a blue blazer with a polka-dot silk handkerchief in its breast pocket, and carried a brown leather attache case. Murder never looked so good.
Johnny 'Jimmy' Roselli in 1965
Surrounded by senators in rapt attention, Roselli offered an assortment of lies and deceptions, sprinkled with a few moments of truth. And when he finished his performance, he confidently stood up, closed his briefcase, and disappeared through a back exit.
Outside, photographers and inquisitive reporters awaited, like a street gang ready to pounce. Flashing camera lights blinded him.
Few photos existed of this mystery witness in shades. Most were mugshots. None captured Roselli’s personal charm, the debonair sense of danger that made women swoon and fellow gangsters refer to him as 'Handsome Johnny'.
'When everyone is dead, the Great Game is finished. Not before,' - Rudyard Kipling, author of Kim, (1901), considered the first modern spy novel.
At a closed-door Congressional hearing in June 1975, gangster Johnny Roselli testified about his role as a 'patriotic' assassin for the Central Intelligence Agency, a top-secret operation full of spies, sex, and unresolved mystery.
With wavy hair and steely blue eyes, Roselli looked like a successful businessman - a 'strategist' as he preferred to be called - or more like the Hollywood B-movie producer he once was.
No run-of-the-mill hoodlum, he wore dark designer sunglasses, dressed in a blue blazer with a polka-dot silk handkerchief in its breast pocket, and carried a brown leather attache case. Murder never looked so good.
Johnny 'Jimmy' Roselli in 1965
Surrounded by senators in rapt attention, Roselli offered an assortment of lies and deceptions, sprinkled with a few moments of truth. And when he finished his performance, he confidently stood up, closed his briefcase, and disappeared through a back exit.
Outside, photographers and inquisitive reporters awaited, like a street gang ready to pounce. Flashing camera lights blinded him.
Few photos existed of this mystery witness in shades. Most were mugshots. None captured Roselli’s personal charm, the debonair sense of danger that made women swoon and fellow gangsters refer to him as 'Handsome Johnny'.
At this shock of public recognition, Johnny’s body stiffened. His affable grin tensed. He’d spent his whole life, both in business and personal affairs, avoiding such moments.
As that rarest of ‘spooks’ - a Mafia hitman turned top-secret spy - Roselli preferred the shadows. He never wanted to be in the spotlight, exposing his many deceptions.
Even his name 'Johnny Roselli' was a phony, one of several aliases he used to avoid revealing his real identity.
Keeping his head down along a Washington street, Roselli hustled away from the Capitol, shunning the paparazzi eager to splatter his face across the next day’s front pages.
They chased after this stylish mobster, hoping for more insights about his highly classified government mission.
'Handsome Johnny' Roselli infiltrated Hollywood in the 1920s, rising up the ranks with Al Capone
Under oath that afternoon, Roselli had fielded questions about the biggest secret in CIA history, kept under wraps for more than a decade. As America soon learned, Roselli and his long-time friend, Chicago mob boss Sam Giancana, were two central characters in an elaborate CIA scheme to assassinate Cuba’s young Communist leader Fidel Castro during the 1960s.
Poison pills, exploding cigars, lethal James Bond-like gadgets, midnight boat raids from Florida with Cuban exiles carrying bombs and long-range rifles - a veritable army of undercover spies, double agents and 'cut-out' handlers - were all part of this ill-fated campaign emanating from the White House.
Historically, the CIA’s murder plot against Castro marked America’s first foray into the assassination business. Kipling’s celebrated 'great game' - the tradition of gentlemen spies engaged in gathering intelligence had been now transformed into the killing games of covert operations, carried out by gangsters and other CIA surrogates.
Not even Roselli’s charm could mask this ugly truth when asked about his mission’s intent.
“To assassinate Castro,” he growled matter of factly in his deep, whiskey-soured voice.
As each detail unraveled before a startled nation, the saga of Giancana and Roselli - two Mafia pals working for the CIA - seemed like a murder mystery and a spy novel all rolled into one.
This complex morality play of Cold War paranoia offered America a bizarre reflection of itself – shattering the heroic Hollywood image of ‘good guy’ agents fending off foreign evil-doers. Instead, this true-life story revealed the much murkier and violent reality of modern espionage by those charged with defending the United States from harm.
As Roselli rushed away from the Senate hearing, reporters peppered him with questions about Giancana's fate and concerns for his own safety. A Washington acquaintance later asked if he feared retaliation because of his testimony.
As always in times of crisis, Johnny never lost his cool.
"Who'd want to kill an old man like me?" he replied.
Exploding cigars were part of the CIA plot to kill Castro
The unholy marriage of the CIA and the Mafia first became known to the American public in the mid-1970s, amid congressional hearings into the agency’s misdeeds and a growing national paranoia about the 1963 assassination of President John F. Kennedy.
For more than a decade, the plot to kill Castro was known only to a few. President Lyndon Johnson didn’t learn about it until his fourth year in office. By enlisting Giancana and Roselli, the CIA “had been operating a damned Murder Inc. in the Caribbean”, Johnson complained. Many troubling questions went unanswered – such as why the Warren Commission examining JFK’s killing was never told of the agency’s Castro conspiracy with the Mafia. Full of his own theories, Johnson predicted: "It will all come out one day."
Yet this spy tale remained an enigma for years, including the mysterious fate of Roselli and Giancana. Not until 2007 did the CIA finally admit that Allen Dulles, its legendary director a half-century earlier, was responsible for offering a sizable bounty to the two gangsters in exchange for Castro’s head. “The documents show that the agency’s actions in the early 1960s still have the capacity to shock,” The Washington Post’s Glenn Kessler said of that long-suppressed internal CIA report known as The Family Jewels.
More pieces in the puzzle emerged in 2017, when the National Archives released thousands of files about the JFK assassination, kept secret in full or part for decades.
Many pertained to the CIA’s Cold War crusade against Castro. Like strands in a ball of yarn, these individual documents revealed a complicated tale far greater than Americans ever realized at the time. Together, they provide the most comprehensive picture yet of America’s first confirmed attempt at state-sponsored assassination of a foreign leader.
These files also help illuminate Giancana’s and Roselli’s shadowy world, which included CIA spies and handlers, beautiful Hollywood women, 'Rat Pack' entertainers like Frank Sinatra in Las Vegas, fellow Mafioso in Chicago, Cuban exile commandos in Miami, J. Edgar Hoover’s snooping FBI and the zealous anti-communism of White House officials in Washington. They reveal the many passions, ambitions and conflicting loyalties among these two outlaw friends, a sort of modern-day “Butch Cassidy and the Sundance Kid”, who rode on planes instead of horses for their getaways.
Giancana and Roselli, at the height of their careers, controlled a multi-million dollar Mafia empire unprecedented in the annals of American crime, arguably bigger than the five families of New York’s La Cosa Nostra combined. Giancana - the gruff, traditionalist mob boss, a widower with three daughters - dreamed of exporting his Midwest criminal enterprise to Latin America. And Roselli, known for his Casanova style, served as the mob’s smooth-talking man in Hollywood before overseeing its casinos in Las Vegas.
The two began as young Turks for Al Capone’s Chicago gang, long before their CIA mission. They had a history of working together, running gambling palaces in Cuba and Nevada and exerting the mob’s will in myriad ways.
With a drink in hand or a woman on their lap, the two Mafia pals could be found in places like the Boom-Boom Room at Miami’s Fontainebleau Hotel, where the CIA scheme to kill Castro was hatched in September 1960. Although they cited 'patriotic' reasons for accepting this assignment, Giancana and Roselli had their own motivations for eliminating the bearded dictator.
When he came to power, Castro closed down the Mafia’s very lucrative casinos in Havana, costing the two gangsters dearly. They still hoped to revive the swank San Souci resort that they had run in Cuba with Spanish-speaking Mafia boss Santo Trafficante Jr.
The JFK files suggest Giancana and Roselli believed that cooperating with the government in such a high-risk venture as Castro’s assassination would earn them a kind of get-out-of-jail-free card that would keep the feds off their backs as they pursued their criminal activity at home. And for a time, their arrangement seemed to work.
Miami, Florida was a secret war zone in the 1960s
Through the prism of these two mobsters, a much larger portrait emerges of America’s top spying agency spinning out of control when the nation most needed its vigilance. Documents show how the CIA conducted a covert war against Castro from a secret camp next-door to the Miami Zoo; how it developed James Bond-like killing devices at the behest of the Kennedys who loved the Bond novels; and how three different CIA directors lied about this secret murder plot so it would never be learned by the public. This undercover quest turned southern Florida into a secret war zone and became a wild whack-a-mole hunt for Castro inside Cuba, all without success.
When Fidel Castro finally died in November 2016 - not from an assassin’s bullet but peacefully asleep in his bed at age ninety – the world was reminded of all the fear he once provoked and why Cuba remains a solitary rogue nation stuck in time.
Instead of a promised savior, Castro had turned his once-prosperous homeland into an armed Communist camp. He enforced his rule with firing squads and merciless prisons. By inviting Russian nuclear weapons into his nation as a way of protecting his despotic regime, he helped incite the 1962 Cuban missile crisis with its threatened Armageddon between the United States and the Soviet Union. Aware of the plots against him, Castro publicly vowed revenge - what experts called ‘blowback’ -- to those who wanted him dead.
Documents describe how Castro’s spy agency and its double agents in Florida 'penetrated' the CIA operation far more than U.S. officials realized; conspired to blow up New York City in a 9/11-like attack; and managed to keep El Comandante from getting killed despite numerous CIA-sponsored attempts. Obituaries about Castro mentioned these repeated assassination tries, but they provided little or no explanation about how he’d managed to avoid getting killed.
As Cuba now re-opens itself to the world, this spy tale serves as a Rosetta stone for understanding all the Cold War hatred and violence that existed for decades - and is still very much with us. The CIA’s Mafia scheme against Castro shows how easily U.S. espionage and law-enforcement agencies were corrupted more than a generation ago, with government-sanctioned murder justified on claims of national security. Talk of assassination pervades this 'great game' just as it does in our Trump era, with Russian-trained spies left for dead, rumors of kompromat and presidential indiscretion, and worries of a new Cold War. Though unfamiliar to many today, this story of espionage and violence offers many important lessons at a time when Americans fear their trusted institutions could again go astray.
In the end, the Castro conspiracy became a Mephistophelian bargain - a promise to do whatever it took to get rid of Cuba’s Communist strongman. Giancana and Roselli expected that their actions against Castro, if not rewarded by the U.S. government, at least would keep them free from future prosecution.
Yet danger pervaded every day of their lives until its vengeful consequences finally caught up with them.
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