Johnny Roselli was one of two top gangsters recruited by the CIA to try and kill Fidel Castro. But Roselli had a life-long secret that this bold assassination plot threatened to reveal.
Johnny Roselli spent most of his life in Hollywood. With both shrewdness and force, he pushed the Chicago mob’s interests in movies, nightclubs and labor unions. Sam Giancana, his biggest pal in the Chicago Mafia organization known as The Outfit, marveled at how Johnny fit in with the showbiz crowd “quicker than you could hum a few bars of ‘Anything Goes’.”
In this land of make-believe, no one had more to hide than Roselli, a man of many secrets and identities.
He was born Filippo Sacco in Esperia Italy on July 4, 1905. With his mother Maria, he came to America six years later – his entry apparently illegal, so that he worried all his life about being deported. They joined his father Vincenzo already working as a shoemaker in Boston’s North End, with its many Italian immigrants.
Young Johnny strove to be accepted as an American. “I stopped talking Italian because of the beatings I received in school,” he remembered.
A life of crime seemed the fastest method of becoming rich in a country that venerated millionaires. “When Christ died on the cross, the closest man to him was a thief, and that’s good enough for me,” he proclaimed. During Prohibition, Roselli relied on bootlegging to raise himself above a grifter.“I was a young fellow with very little education,” he later testified. “Just buying and selling a little liquor here and there, trying to do anything I possibly can to make a living.”
Violence became part of this mix. FBI records indicate Roselli, under the name Philip Sacco, was charged with larceny and selling heroin. He reportedly killed the informant who implicated him before fleeing Boston. Sacco landed in Chicago, taking on a new name and identity. His new last name was inspired from a book mentioning Cosimo Rosselli, a 15-century Italian painter, who helped decorate the Vatican’s Sistine Chapel.
Johnny’s choice of pseudonym begged a question: What form of devotion or delusion motivates a gangster to adopt the surname of an artist known for painting scenes of the Nativity and The Last Supper? Or did Roselli simply recast himself the way Hollywood picked out stage names like John Wayne, Marilyn Monroe or Cary Grant?
Whatever personal insights this identity change might suggest, Roselli took care to hide his origins. No questions about his past were tolerated. He forged birth records to make it appear he’d been born in the Windy City. Over time, he’d use other aliases, including spelling variations of Roselli with a double “s”, to cover his tracks.
Yet no matter how carefully Roselli masked himself in stylish clothes and ill-gotten wealth, scrubbed away any hint of an accent in his voice, the fear of being found out – exposed as an illegal immigrant without proper papers—never left him.
In Depression era Chicago, Roselli became a soldier in the Capone gang and quickly a driver for the boss himself. After a bout of tuberculosis, Johnny was sent to the warmer climate of Los Angeles, as the Chicago gang’s shakedown artist in the burgeoning movie industry. Roselli reported to local Mafia boss Jack Dragna but he never lost touch with his original sponsors, who got a piece of all his deals.
In Hollywood, Johnny proved a natural. He dealt with producers and film executives, accustomed to fakery and assumed names, who knew that behind his slick ingratiating demeanor was a well-dressed killer.
“You either click with people or you don’t,” Roselli explained. “The secret is not to look in their eyes. You pick a spot on their forehead and zero in. That way you don’t blink, you don’t move. It intimidates the hell out of them.”
Along swanky Rodeo Drive in May 1966, on his way to the Friars Club in Beverly Hills, Roselli remained discreet, aware that the FBI was still tailing him, keeping track of every move. Wise guys and other associates who wished to discuss business with Roselli usually received an advance preparatory phone call.
“Shamus, here,” said the telephone voice, clearly Johnny’s. “Call at one o’clock.”
Later at that precise time, the business partner would reach Roselli on a special private telephone that Johnny had access to at the Friars Club.
Similarly, when Florida don Santo Trafficante Jr. came to town with his wife, Johnny made sure their dinner together wasn’t interrupted. He brought along a private eye to look out for any signs of snooping federal agents.
Given all his precautions, Roselli must have been shocked around noon on May 5, when two men abruptly approached him at the corner of Rodeo and Brighton Way. The two men identified themselves as FBI agents wanting to talk. The Beverly Hills confrontation took place near Cartier’s jewelry store with its elegant window displays.
“See my attorney,” Roselli growled, without breaking stride.
The agents kept walking with him along the sidewalk. In front of him, they waved a photograph of a small boy as well as an old birth certificate. If Johnny got a momentary glance at the two items from his past, he didn’t let on.
“Filippo Sacco”, the FBI agents called out. They repeatedly mentioned his “true name” over and over.
The bureau’s constant sleuthing had discovered Roselli’s hidden identity, by far his biggest secret.
Like prizes they won at a scavenger hunt, the agents held aloft the photo of young Filippo Sacco and his mother, taken when he was in grade school in Boston. The birth certificate indicated Roselli wasn’t born in Chicago, as he previously claimed, but came to America illegally as an immigrant from Italy. Investigators discovered a phony birth certificate, filed in 1936 for “Giovanni Roselli” in Chicago, that had a forged signature.
“We know where you were born and when you entered the United States,” the agents informed him, as they later recounted in an FBI memo.
Roselli gave an unconvincing denial. “I don’t know what you are talking about,” he insisted.
But Johnny surely knew what this discovery meant. After years of fakery and covering his tracks—fraudulent testimony about his identity, and phony documents with incorrect dates and different spellings to his surname – Roselli came face to face with who he really was, his true identity.
The little boy in the photo had long ago left Boston as a young adult, under suspicion for murder or some other unknown deed. As if re-inventing himself under duress, he became “Johnny Roselli” to his fellow mobsters in Chicago and to all who met him in the bright lights of Hollywood and darkened casinos of Vegas and Havana. It wasn’t clear if even those closest to him – such as pal Sam Giancana or his former wife June Lang or anyone else—fully knew his story.
The feds now had something on Roselli that he feared more than a criminal charge. They could deport him, just as the federal government had done to other Mafia figures such as Lucky Luciano and, more recently, Trafficante’s good friend, Carlos Marcello, the don of New Orleans.
The two FBI men told Roselli the bureau wanted his cooperation, intending to flip him as an informer. They wanted to meet Johnny in three days at DuPar’s Restaurant in Thousand Oaks, and gave him a business card with its address.
Johnny first moved to take the card and then, instinctively, rejected it.
“Go see my attorney,” he repeated.
The confrontation provided only a hint of the high stakes for the FBI as well as Roselli. Since the Kennedy administration, especially in the wake of JFK’s death, Hoover’s investigators had pursued why the CIA recruited Roselli and Sam Giancana.
In the complex political calculus of Washington, the FBI chieftain sensed an advantage over the rival spy agency if his agents could piece together the extraordinary story of how the two mobsters became government approved assassins against Castro.
By May 1966, the FBI had mostly figured it out. The CIA “compromised themselves by dealing with Roselli when they had him contact Sam Giancana, head of the Chicago ‘family’ of La Cosa Nostra, to get someone to assassinate Castro,” explained the bureau’s LA office in a May 23 memo to Hoover’s deputy director, Cartha DeLoach. The memo stressed Roselli’s potential as a “top echelon criminal informant,” the highest ranking for a snitch.
Roselli clearly knew more about the Mafia’s machinations in American business and politics than the celebrated gangster Joseph Valachi, who made headlines with his 1963 testimony as an FBI informer.
The childhood photo of young Sacco with his mother “apparently touched a sensitive spot” with Roselli, the memo said. It called for the bureau to “capitalize on his inner turmoil to develop” Roselli as a top informant.
Privately, Johnny vowed to kill whoever had betrayed him. Little did he know that the photo, birth certificate and longtime secret about his origins – the FBI’s biggest break in its long-running surveillance of Roselli – had been revealed purely by happenstance.
It began when the feds noticed Salvatore Piscopo, Johnny’s fellow Los Angeles hoodlum, had failed to pay his taxes on bookmaking profits at various California horse racetracks. Like a small bug suddenly caught in a Venus flytrap, Piscopo (alias “Louie Merli”) panicked at the thought of going to jail. Inadvertently, he would lead agents to Johnny’s secret.
For nearly thirty years, Piscopo had performed a number of gangland tasks for Roselli. According to Vegas legend, Piscopo served as a getaway car driver for the 1947 mob hit on Ben “Bugsy” Siegel, the legendary casino owner. Bugsy was shot dead in the Beverly Hills home of his girlfriend, Virginia Hill, who would also have an affair with Roselli.
Piscopo took note of Johnny’s success with the ladies, enough to mention it later to the FBI. He said Roselli “is very good looking and all the girls go for him.”
Presciently, Roselli worried about Piscopo’s judgment. A possible slip of the tongue could land them both in trouble. He warned Piscopo that “a person’s own telephone is the biggest stool pigeon in the world and never use it to talk to people.”
As FBI surveillance followed Piscopo around town, they secretly photographed him meeting an unknown person at the airport. The stranger carried an overnight bag and gave Piscopo an affable hug, like a long-lost brother. Indeed, he was Johnny’s brother—Albert Sacco.
Albert flew back to Boston with a satchel of cash, which would be given to his aged mother, Maria Sacco. For years, the money from Johnny in Hollywood had helped his family in Boston stay afloat financially, including his brother who worked as a janitor. The exchange usually took place once a year with Johnny’s trusted bagman, Salvatore Piscopo, serving as his family’s conduit.
The discovery of Johnny’s brother was a boon for investigators. Under the veil of secrecy and great care, the FBI put together a complete dossier on Roselli’s personal background. It took more than two years to find and piece together all the documents in various cities.
When the FBI finally approached Roselli in May, 1966, the agents tried to appear warm and friendly.
“This has nothing to with you personally, John,” said one of the agents, almost apologetic. “It’s a matter of national security.”
Though Johnny acted unperturbed, he immediately contacted his local defense attorney, Jimmy Cantillon, who put the FBI on notice not to speak with his client.
The next day, Roselli flew to Washington, where he spoke in confidence to Shef Edwards, the recently retired CIA chief of security. Through buffers and go-betweens, Shef had overseen Johnny’s covert work against Castro. Johnny explained the Sacco situation without seeking a deal. “I did not ask him to get the FBI off my back,” Roselli later claimed.
Edwards, an old CIA hand, chalked off the immigration matter as an inter-agency rivalry within the government. As Johnny remembered, “they had a big feud going on between the FBI and the CIA.”
But the family matter clearly haunted Roselli. He showed Shef a copy of the photograph—left anonymously outside his apartment—of the four-year-old boy and his mother. He acknowledged to Shef that “the child was himself at that age,” records show.
The retired CIA man inquired about Roselli’s mother but Johnny remained “very touchy on this.” Johnny angrily labeled this FBI attempt to turn him into an informant as pure “blackmail.”
At first, Johnny had no idea who betrayed him. The FBI implied their discovery of Roselli’s true identity—and the family he left behind in Boston—was the sole result of their sleuthing of documents rather than informant Sal Piscopo and his determination to stay out of jail. Smelling a rat, Johnny swore one day he’s find out the name of his double-crosser and get even.
In alerting the CIA, Roselli assured Shef Edwards that he’d honor his commitment to keep his mouth shut and not to speak about his role in the agency’s top-secret plot to assassinate Cuban leader Fidel Castro. Any public disclosure of these previous plans would undoubtedly prompt all sorts of recriminations, including doubts about a possible Cuban angle to the JFK assassination.
As Shef suspected, Johnny had become a pawn between America’s two premier investigative agencies. In a formal memo, CIA officials let Hoover’s FBI know they didn’t want Edwards questioned as a witness. They said Edwards’ participation might “open the door” to exposing “an extremely sensitive intelligence operation.” Most tellingly, the CIA admitted Roselli had the agency “in an unusually vulnerable position.”
No one knew for sure what Johnny might do if he faced federal prosecution. And it came as a big surprise, especially to Roselli, when he was indicted for something far more serious than an immigration violation.
Thomas Maier is an award-winning investigative reporter and the author of six books. This is excerpted from “Mafia Spies: The Inside Story of the CIA, Gangsters, JFK and Castro,” published this month by Skyhorse Publishing.