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Chicago’s ‘Mafia Spies,’ CIA Castro plot detailed in book by ex-Sun-Times writer

Chicago Outfit boss Sam Giancana (center, foreground) and his mob pal Johnny Roselli were recruited by the CIA during the Cold War to kill Cuba’s dictator Fidel Castro.

Chicago Outfit boss Sam Giancana (center, foreground) and his mob pal Johnny Roselli were recruited by the CIA during the Cold War to kill Cuba’s dictator Fidel Castro. | Skyhorse Publishing

During the Cold War, Chicago’s top gangster Sam Giancana and his mob pal Johnny Roselli were recruited by the CIA to kill Cuba’s dictator Fidel Castro — a plan that remained hidden from the public for more than a decade. New details about this plot were revealed by the National Archives when President Donald Trump ordered long-suppressed JFK assassination documents released. But back in 1960, law enforcement had little idea of what these two outlaw spies were up to with America’s spy agency.

This is the first of three parts excerpted from the new book “Mafia Spies: The Inside Story of the CIA, Gangsters, JFK and Castro” (Skyhorse Publishing, $25.99) by Thomas Maier, a former Sun-Times reporter whose other books include “Masters of Sex,” which was made into a Showtime TV series.

After several months, “Little Al” — named for Al Capone — proved more valuable than a thousand spies.

The hidden microphone, planted illegally in the downtown Chicago headquarters of Sam Giancana’s Outfit, yielded a wealth of information for the FBI. More than any snitch, “Little Al” opened the eyes of FBI chieftain J. Edgar Hoover to the Mafia’s widespread criminality around the country in the early 1960s.

One recorded conversation between mob boss Giancana and his senior consigliere Tony Accardo seemed like an encyclopedia of La Cosa Nostra. Sam explained what happened at a recent national commission meeting, identifying all the regional dons and their brewing vice.

“It is difficult to understand just how excited we were when we taped this conversation and then played it back, word for word, many times in order to gain the full impact of what was discussed,” recalled William Roemer, a top Chicago agent on the FBI’s aptly named Top Hoodlum Squad.

“Little Al” was so successful that the FBI finally decided to go ahead and install a second bug in Giancana’s suburban hangout the Armory Lounge, a Forest Park bar and grill with a giant neon, flashing sign in front.

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The federal government’s initial constitutional worries about illegal eavesdropping now gave way to more practical concerns. Chicago FBI agents fretted over how to place a hidden microphone in the Armory without getting caught. Most patrons were Giancana’s gangland associates. They knew the awful penalty for talking to the feds.

With fellow hoodlums, Sam insisted on omerta, the Mafia’s code of silence, and the vital importance of keeping their eyes open and lips sealed. “You see that f—ing fish?” Giancana once barked at a nosy associate, calling attention to a swordfish trophy hanging from the wall. “If he’d kept his mouth shut he wouldn’t have got caught.”

Giancana’s mob hideaway, not far from his home in Oak Park, was more isolated and protected than the Outfit’s downtown headquarters. Though miles from the South Side slaughterhouses — and pungent odors that gave Chicago its title “hog butcher for the world” — this “command post” had a gritty, industrial park appearance that compounded the grayness of winters and made sunny places like Vegas, Miami and Havana so appealing.

While the Armory Lounge was used to greet visiting hoodlums and friendly entertainers like Frank Sinatra, it also could be a fortress of paranoia. Through a window, Sam sometimes peered with binoculars at the empty parking across the street owned by the U.S. Navy. He kept staring ahead, hoping to catch in the shadows some spy watching him. FBI records show Giancana “apparently feels this lot is being used continually for surveillance purposes of his activities.”

Eventually, federal agents came up with a masterstroke of deception. They confronted the Lounge’s night janitor with an FBI “wanted” poster of a suspect that looked vaguely like him. The G-men asked the janitor to come down to headquarters to clear up the matter. The janitor reluctantly agreed.

Arriving downtown, the agents asked the janitor to empty his pockets before going off to another room to be fingerprinted. Over the next several minutes, while the janitor was rolling each inky finger onto a print card, an expert locksmith secretly made a copy of the Armory Lounge keys.

Soon after, in the wee hours before dawn, the FBI entered the Armory Lounge. They placed a large, pineapple-shaped microphone behind a wall where Giancana kept an office. Then the agents strung a connecting wire down a wall to the basement and eventually outside, where a signal would be transmitted to the FBI.

The new listening device, nicknamed “Mo” for the Lounge’s most prominent habitué, helped Roemer and the FBI sleuths learn of another startling and previously unknown mystery.

Along with conversations about the Mafia’s national commission and deals with corrupt local politicians, the FBI heard Giancana discussing plans to kill Fidel Castro.

Hoover and his G-men had no idea of the CIA’s top-secret assassination plan featuring the two Mafia hoodlums in prominent roles. Details from the listening devices, however, connected the dots to this puzzle for the FBI agents. As Roemer recalled, “Very soon we learned why Sam had been so knowledgeable about Cuba.”

On Oct. 18, 1960, Hoover alerted the CIA. His memo claimed Giancana knew all about a murder plan against a foreign leader, Fidel Castro. On its face, the claim seemed outlandish and, if successful, sure to cause an international incident.The FBI director based his report on “a source close to Giancana.” Hoover didn’t reveal to the CIA whether his source was a hidden microphone like “Little Al” or some secret informant.

Fidel Castro.

Fidel Castro. | Skyhorse Publishing

But FBI records, released publicly decades later, show the first tip about the Castro murder plot apparently came from John W. Teeter, a businessman then married to Christine McGuire, part of the then-famous singing trio the McGuire Sisters. A few months earlier, Christine’s sister, Phyllis McGuire, had begun dating the grizzled but charismatic Giancana — an affair that made headlines around the world as if it were a modern-day “Beauty and the Beast” tale.

Privately, Teeter approached the bureau in July 1960 about the family’s deep concerns that Phyllis had fallen under the sway of a gangster and couldn’t be talked out of the troubling relationship.

Teeter “remarked that Phyllis McGuire is a headstrong know-it-all type who is unable to be controlled in situations such as this” and is receptive to Sam’s money and very expensive gifts, an FBI memo described. Apparently Phyllis had no idea of her brother-in-law’s cry for help to the feds.

Two months later, the stakes intensified. Teeter alerted the FBI that Giancana had shared details about a Castro assassination plot during dinner together in New York City. The McGuire Sisters were in town on business. The two couples — Sam and Phyllis, sister Christine and her husband John Teeter — gathered at an Italian restaurant. When the leisurely conversation turned to Cuba, Sam declared he had some inside information. At first, Phyllis and Christine expressed doubts, especially when Sam confidently claimed Castro would “be done away with very shortly.”

Giancana wasn’t deterred. As waiters and other customers swirled around them, he spelled out the killing scheme being launched in Florida. Stunningly to Teeter’s ears, Sam used the term “assassin.”

According to Giancana, he met with the would-be-assassin on three occasions. The last took place on a boat docked outside the Fontainebleau Hotel in Miami Beach. Sam boasted that “everything had been perfected for the killing.” Under the plan, the unknown assassin had arranged with a mystery “girl” to drop a poison pill into Castro’s food or drink.

Acting on this tip, Hoover’s warning to the CIA appeared urgent because Giancana “assured those present” that the Castro killing would take place in November 1960 — a few weeks away.

The bureau took swift action. Records show Hoover directed FBI agents to report immediately if Giancana flew to Miami, to monitor his long-distance calls and see whether he met with any “anti-Castro elements.” Hoover also instructed agents in Florida to find out the “identity of the person who allegedly met with Giancana at a boat docked at Fontainebleau Hotel.”

To protect Teeter’s identity, the FBI instructed undercover agents to be “discreet so as not to jeopardize New York source.” When conducting surveillance, Teeter warned, agents should remember that all three McGuire Sisters could “read lips from any distance” and were “expert” at it.

Who did Giancana have in mind in referring to Castro’s “assassin?” Congressional investigators later suggested Richard Cain, the corrupt former Chicago cop under Sam’s control, was working at that time with “a mistress of Castro to accomplish the deed.” The unsuccessful Cain assassination plan was an independent Mafia enterprise, the investigators concluded, not the CIA’s pending conspiracy.

Unaware of the CIA’s involvement with the Mafia, Hoover dispatched his October 1960 memo to America’s top spy agency. He repeated Giancana’s boast that Castro was “to be done away with very shortly.”

Hoover’s missive landed with a proverbial thud on the desk of Richard Bissell, the second-in-command at CIA to director Allen Dulles. The overseer of the agency’s anti-Castro campaign had no intention of stopping, regardless of the FBI director’s warning.

“Hoover’s rivalry with the CIA was one of long standing,” observed CIA historian Thomas Powers. “This [memo] should have given Bissell pause, but he went ahead with the plan anyway, a fact which ought to be taken as tacit confirmation of the pressure Bissell felt to ‘get rid of Castro.’ ”

CIA director Allen Dulles (from left), deputy director Richard Bissell, President John F. Kennedy and John McCone, who replaced Dulles as CIA chief. | Skyhorse Publishing

Years later, Bissell’s recollection was murky. But Bissell admitted he did share Hoover’s warning memo with Shef Edward, the CIA’s head of security. “I am sure I referred it to Mr. Edwards who was the individual in the Agency directly in charge of that liaison with Giancana,” Bissell testified, “and I probably asked Mr. Edwards whether this represented a threat to the security of the whole relationship.”

Little exists in declassified documents about the CIA’s reaction to Hoover’s warning. Apparently there was never a formal response to the FBI chief.

In reality, the spy agency didn’t want to draw attention to its ongoing use of Giancana and his Mafia pal Johnny Roselli as “patriotic assassins” in the covert war against Castro.

Author Thomas Maier.

Author Thomas Maier, a former Chicago Sun-Times reporter whose other books include “Masters of Sex,” which became a Showtime TV series. | Provided photo