Sam Giancana: The Mob Boss Who Worked With the CIA — Then Was Silenced at Home

They called him Mooney. For two decades, Sam Gianana ran the most profitable criminal empire in America. He fixed elections, shared a mistress with the president, and helped the CIA try to kill Fidel Castro. But on June 19th, 1975, the night before he was supposed to testify  before Congress about all of it, someone walked into his basement kitchen in Oak Park, Illinois, and put seven bullets in his head.

 One in the mouth, six in a circle around his chin and neck. A clear message from the Mob. This is the story of the  gangster who knew too much and paid for it with his life. Sam Jianana was born Salvatore Jangana on May 24th, 1908 in a neighborhood on Chicago’s near west side they called the patch.

 It was little Italy, packed tight with Sicilian immigrants who had come to America with nothing and built their world on Taylor Street. The tenementss were cramped, the streets were dirty,  and opportunity came in only two flavors: legal or illegal. For most kids  in the patch, illegal paid better. Sam’s father was a pushcart peddler.

 His mother died when he was two. He grew up wild, running the streets, skipping school, getting into fights. By the time he was 10, Sam had already been arrested for autotheft. By 14, he had dropped out of school entirely. He could not read well, could not write much, but he could hustle, and more importantly, he could hurt people without thinking twice about it.

 In the 1920s, Sam fell in with a gang called the 42 Gang, named after Alibaba and the 40 Thieves. These were not kids playing at crime. The 42 Gang was a farm team for the Chicago Outfit, the mob organization that ran the city. They hijacked trucks, robbed warehouses, beat up union organizers, and did whatever the bosses needed done.

 The 42 gang produced some of the outfit’s most vicious killers. Sam Gianana was one of them. Somewhere along the way, Sam picked up the nickname Mooney. Some said it was short for Momo, which meant crazy in Italian. Others said it came from his ability to moon people, to charm them, to make them trust him  right before he stabbed them in the back.

 Either way, the name stuck. By the time he was in his 20s, Sam had graduated from the 42 gang to the big leagues. He went to work for Paul the waiter Ra and Tony Joe Batter Zakardo, two of the most powerful men in the Chicago outfit. Sam ran Policy Wheels, the illegal numbers racket that was the mob’s bread and butter in black neighborhoods on the south side.

 He was good at it. He was an earner. And in the mob, earners get promoted. Sam also did the dirty work. Enforcement, collections, the occasional hit. He didn’t flinch. He didn’t hesitate, and he didn’t talk. By the 1940s, Sam Gianana was a made man, a full member of the outfit, and he was rising fast. In 1942, Sam was arrested for bootlegging and draft evasion.

 He told the draft board he was a constitutional psychopath, too crazy to serve. The army believed him and sent him home. The outfit believed him, too, in a different way. They knew Sam was crazy enough to do whatever needed to be done. By the early 1950s, Sam was running rackets all over Chicago. He controlled the policy wheels on the south side, the casinos in Cicero, the wire rooms that handled bets from across the Midwest.

 He was a Cardo’s top lieutenant. And in 1957, when Aardo decided to step back from day-to-day operations, he handed the  keys to the kingdom to Sam Gianana. At 49 years old, Sam Mooney Gianana became the boss of the Chicago outfit. For the next decade, he would be the most powerful mobster in America. When Sam Gianana took over the Chicago outfit in 1957, he inherited an empire.

 The outfit controlled gambling, prostitution, lone sharking, and labor racketeering across the Midwest. They had politicians on the payroll, judges in their pocket, and cops looking the other way. Most importantly,  they had Bl Vegas. The Chicago mob had been skimming money from Las Vegas casinos since the 1940s.

The Stardust,  the Desert Inn, the Riviera, all of them had hidden Chicago money behind them. Cash came in through the front door as bets got counted in the cage and a percentage got skimmed off the top before the casino ever reported it to the IRS. The skim went straight back to Chicago.

 Millions of dollars a year, untaxed, untraceable. Sam Jianana’s job was to keep that money flowing. But Sam wanted more than just money. He wanted respect. He wanted to be seen. And that is where he differed from his predecessor. Tony Aardo had been a ghost. He lived quietly in a mansion in River Forest,  played golf, and never talked to reporters.

 Sam Gianana did the opposite. He started showing up in public. He hung out with celebrities. He dated singers. He flew to Las Vegas and sat ringside at the Sands where Frank Sinatra and the Rat Pack performed. Sinatra and Sam became close.  Frank introduced Sam to everyone. Dean Martin, Sammy Davis Jr., Peter Lofford, all of them knew Mooney.

They drank with him. They gambled with him. And they did not ask too many questions about what he did for a living. Frank needed the outfits help running casinos. Sam needed Frank’s glamour to legitimize himself. was a perfect arrangement. In 1960, Sam fell in love. Her name was Phyllis Maguire, one-third of the Maguire sisters, a singing group that had sold millions of records.

Phyllis was beautiful, talented, and 20 years younger than Sam. She was also dating other men. Sam did not care. He showered her with gifts, jewelry, furs, cash. He flew her to Europe. He bought her a mansion in Las Vegas. He was  obsessed. The FBI noticed. They had been watching Sam for years, but now they started following him everywhere.

Agents sat outside his house on South Winona Avenue in Oak Park. They tailed him to restaurants, to nightclubs, to the airport. They bugged his phone. They bugged his car. They even bugged his girlfriend’s dressing room. The surveillance was constant, suffocating, and it was about to get worse. Because while Sam was living the high life in Vegas, another powerful family had noticed him, the Kennedys.

In 1959, according to multiple sources, including Sam’s own family, Joe Kennedy, the patriarch of the Kennedy clan, reached out to the Chicago mob. Joe wanted his son Jack to run for president, and he wanted help. Joe Kennedy knew the mob. He’d worked with them during Prohibition, smuggling  whiskey into the country, making millions.

 He understood how they operated. And he understood that in Chicago, the  outfit controlled votes. If the mob wanted you to win Cook County, you won  Cook County. It was that simple. The story goes that Joe Kennedy met with Sam Gian Kana at a hotel in Chicago. Joe asked  for Sam’s help delivering Illinois in the 1960 election.

 In exchange,  Joe promised that once Jack became president, the government would back off the mob. No more raids, no more prosecutions, business as usual. Sam agreed. Why wouldn’t he? The deal made sense. Help elect a president. Get the feds off your back. It was just another transaction.  In November 1960, the presidential election between John F.

Kennedy and Richard Nixon came down to  a handful of states. Illinois was one of them. The vote in Chicago was critical, and the outfit delivered. Sam’s crew went to work. They sent precinct captains into the neighborhoods. They rounded  up voters, some living, some dead. They stuffed ballot boxes.

 They intimidated poll watchers. They did whatever  it took. When the dust settled, Kennedy won Illinois by fewer than 9,000 votes. Nationally, he won by onetenth of 1%. Sam Gianana believed he’d put a president in the White House. He believed  Joe Kennedy owed him. He believed the deal would hold. He was wrong.

 Once JFK took office,  his brother Bobby became attorney general. And Bobby Kennedy hated the mob. He’d made his name in the late 1950s, going after mobsters as chief counsel for the Senate Rackets Committee. He’d interrogated Sam Gian Kana on national television in 1959, humiliating him, mocking him, asking him if he giggled like a little girl every time he took the Fifth Amendment.

 Bobby didn’t forget, and he didn’t forgive. As attorney general, Bobby launched an all-out war on organized crime. He doubled the number of FBI agents assigned to mob  cases. He authorized wiretaps, surveillance, informants. He went after the outfit harder than any prosecutor in  history. Sam felt betrayed.

 He’d delivered Chicago. He’d helped make Jack Kennedy  president. And now Bobby was destroying his organization. The deal was off. The Kennedys had double crossed him. And Sam Gian Kana never forgot a double cross. In 1960, while the Kennedy campaign was ramping up, the CIA had a problem.

 Fidel Castro had taken over Cuba  and the agency wanted him dead. They had tried everything. Exploding cigars, poison pens, sniper rifles. Nothing worked.  So, they decided to try something different. They decided to hire the mafia. The logic was simple. The mob had run Havana before Castro. They had owned the casinos, the hotels,  the brothel.

 When Castro came to power, he kicked them all out and seized their assets. The mob wanted Castro dead as much as the CIA did. So, the agency reached out. The CIA point man was a guy named Robert Mayhew, a former FBI agent turned private investigator who did dirty work for the government. Mayhew contacted Johnny Rosselli, a mobster who had been the outfits man in Los Angeles and Las Vegas for years.

 Roselli agreed to help and he brought in Sam Gian Kana. The plan was called Operation Mongoose. The idea was to use mob contacts in Cuba to slip poison into Castro’s food or drink. The CIA provided the poison pills. The mob provided the access. It sounded simple. It was not. The first problem was getting the pills into Cuba.

The second problem was finding someone Castro trusted enough to  get close to him. The third problem was that Castro was paranoid. He had food tasters. He changed his schedule constantly. He slept in different places every night. Killing him was nearly impossible. Sam and Johnny tried anyway. They  sent the pills to Havana through mob contacts.

 They bribed officials. They recruited agents, but every attempt failed. Castro survived. Meanwhile, the CIA kept asking for more help. They authorized other plots. Poison wets suits. Booby trap seashells. Mafia snipers. None of it worked. Castro kept giving speeches, kept running Cuba, kept being alive. The relationship between the CIA and the mob got stranger.

Agency handlers met with mobsters in hotel rooms and safe  houses. They passed cash under the table. They authorized hits on foreign leaders. And all of it was off the books, deniable, illegal. Sam Gianana loved it. Here he was,  a gangster from the west side of Chicago working with the United States government. He had access.

 He had leverage. He had secrets, and secrets in Sam’s world were currency. But the operation was doomed from the start. The CIA never trusted the mob completely. The mob never trusted the CIA, and Castro somehow kept surviving. By 1963, Operation Mongoose was essentially over. The attempts on Castro’s life had failed.

 The Bay of Pigs invasion had failed. The Cuban missile crisis had brought the world to the brink of nuclear war  and the Kennedys who had authorized the whole mess were looking for a way out. Sam Gianana meanwhile had been keeping score. He had helped the CIA try to kill a foreign leader. He had helped Joe Kennedy get his son elected.

 And what did he get in return? Bobby Kennedy prosecuting his friends, the FBI following him to the bathroom,  and a government that was about to cut him loose. Sam was sitting on enough secrets to bring down a presidency. The only question was whether he would ever use them. While Sam Jian Connor was plotting with the CIA and dodging Bobby Kennedy’s Justice Department, the FBI was building a case against him.

 Jay Edgar Hoover wanted Sam bad,  and the bureau’s weapon of choice was surveillance. By the early 1960s, the FBI had wire taps on Sam’s phones, bugs in his house, and agents following him 24 hours a day. They recorded his conversations with mob associates. They photographed him with celebrities.  They documented every move he made.

 The surveillance was so intense that Sam started joking about it. He would wave at the agents. He would send  them coffee. He would drive in circles just to waste their time. But the wire taps picked up something. the FBI did not expect. Sam was having an affair with a woman named Judith Campbell Exner.

 And Judith was also sleeping with President John F. Kennedy. Judith Campbell was a dark-haired beauty who had been introduced to John F. Kennedy by Frank Sinatra in early 1960. She and the president began an affair that lasted for years. She visited the White House. She called him on private lines and at the same time she was also seeing Sam Gianana.

 The implications were staggering. The president of the United States was sharing a mistress with the head of the Chicago mob. If that got out, it would destroy Kennedy politically, and Sam knew it. The FBI knew it, too. Hoover informed the president in March 1962 that they were aware of the affair. The calls from Judith to the White House stopped immediately, but the damage was done.

 Sam Jankana now had comat on the most powerful man in the world. Then there was Marilyn Monroe. According to Sam’s brother, Chuck and nephew Sam, who wrote a book called Double Cross decades later, Sam Gianana was alleged to be involved in Marilyn Monroe’s death. The book claims that in August 1962, the CIA asked Sam to eliminate Marilyn because she knew too much about the Kennedy brothers, about the mob, about everything.

 The book alleges that Sam sent men to Marilyn’s house on August 4th, 1962. They waited until she was alone. They taped her mouth. They inserted a barbiterate suppository that would kill her quickly without leaving traces of pills in her stomach. And they made it look like suicide. The official cause of death was ruled probable suicide by overdose.

 But the story has never sat right with investigators. There were inconsistencies. The timeline did not match. Witnesses changed their stories and Marilyn had been talking about going public with what she knew about the Kennedys. Whether Sam was actually involved is still debated, but one thing is certain, Sam had dirt on the Kennedys.

  He had access, he had motive, and he had the capability. The surveillance continued. The wiretaps kept recording. And in the background, Sam Jankana kept collecting secrets. He knew about the CIA plots. He knew about the women. He knew where the bodies were buried, literally and figuratively. And then on November 22nd, 1963,  everything changed. President John F.

 Kennedy was shot in Dallas at 12:30 p.m. On November 22nd, 1963, Lee Harvey Oswald was arrested. Two days later, Jack Ruby walked into  Dallas police headquarters and shot Oswald dead on live television. Jack Ruby was a nightclub owner with mob connections. He had run clubs in Dallas since the late 1940s, and he had been reporting to the Chicago outfit the entire time.

 That’s where the theories start. In the years since the assassination, multiple sources have claimed that the mob was involved in killing John F. Kennedy. The motive was clear. Bobby Kennedy’s war on organized crime had crippled the outfit. Prosecutions were up. Informants were talking. The skim from Las Vegas was being disrupted.

 The mob wanted Bobby gone and the only way to get rid of Bobby was to kill his brother. According to the book Double Cross, Sam Gianana admitted to his brother Chuck that he played a role in the assassination.  Sam allegedly told Chuck that he had met with both Lynden Johnson and Richard Nixon before the killing and that they were aware of the plan.

Johnson had everything to gain. Nixon had mob connections going back decades. The book claims the CIA was involved, too. The same agents who had recruited Sam to kill Castro allegedly used the same networks  to kill Kennedy. Lee Harvey Oswald had spent time in Russia. >>  >> He had intelligence connections.

He was the perfect psy. And then there was Jack Ruby. Jack Ruby’s shooting of Oswald made no sense unless you understood Ruby’s role. He was not a lone nut avenging the president.  He was a mob errand boy who had been told to shut Oswald up. Ruby walked into that police station, shot Oswald in the gut, and guaranteed that the truth would never come out.

 Ruby died  of cancer in prison in 1967, just weeks before he was supposed to testify again about the assassination. He told reporters  before he died that the truth would never be known because the people involved were too powerful. Did Sam Gian Kana order JFK’s death? Probably not directly.

 But did he know about it? Did he help? Did he provide resources, contacts, and cover? The FBI thought so, investigators thought so. And decades of research  suggests that the mob, the CIA, and possibly elements of the government all had pieces of the puzzle. Sam John Kana never admitted anything publicly, but privately  to family members.

 He hinted that he knew more than he could ever say, and that knowledge would eventually get him killed. After JFK’s assassination, Bobby Kennedy resigned as attorney general in 1964. The war on the mob slowed down, but the FBI did not stop. They kept the pressure on Sam Gianana. In 1965, a federal grand jury in Chicago subpoenaed Sam to testify about mob operations.

 Sam refused. He took the fifth amendment on every question. The judge held him in contempt and sent him to jail for a year. Sam was released in 1966. By then, the outfit had changed. Tony Aardo was still the real power behind the throne, but younger guys were moving up. Sam’s position was weaker. The surveillance had made him a liability.

He could not operate without the feds watching.  He could not meet with his crew. He could not make money. So, in 1966,  Sam made a decision. He left the country. He moved to Quavaka, Mexico,  a resort town south of Mexico City. He lived in a villa, played golf, and tried to stay out of sight.

 But the FBI and the CIA never stopped watching him. They knew where he was. They knew who he met with, and they waited. Sam stayed in Mexico for 8 years. During that time, the outfit kept running in Chicago. The skim from Vegas continued. The rackets kept humming. Sam  was out of the picture, but the machine he had helped build kept working without him.

Then in 1974, the Mexican government deported him. Officially,  they said his visa had expired. Unofficially, pressure from the US government  had made Sam unwelcome. He flew back to Chicago and moved into the basement apartment of his daughter Bonnie’s house in Oak Park, the same quiet suburb where he had grown up. Sam was 66 years old.

He was out of power. He was out of money, and he was about to become the most dangerous man in America because in 1975, the US Senate decided to investigate the CIA’s involvement in assassinations of foreign leaders. The committee was led by Senator Frank Church and one of the first people they wanted to talk to was Sam Gianana.

The Church Committee subpoenaed Sam in June 1975. They wanted him to testify about Operation Mongoose, the plots to kill Castro, and the CIA’s relationship with the mob. Sam was scheduled to appear before  the committee on June 24th. He never made it. On the evening of June 19th, 1975, Sam Gian Kana sat alone in the basement apartment of his daughter Bonnie’s house at 1147 South Winona Avenue in Oak Park, Illinois. The house was quiet.

 Bonnie and her husband were out of town. Sam was by himself, which was rare these days. The FBI had been watching him for years,  but tonight, for whatever reason, they were not outside. Sam was in the kitchen cooking a late dinner. Sausages with peppers, escarole, beans, simple food, the kind his mother would have made back in the patch 50 years ago. Comfort food.

 Food that reminded him of a time before the power, before the money, before the secrets that were about to get him killed. It was around 1000 p.m. when someone knocked on the door. Sam walked over and opened it. Whoever was standing there, Sam knew them. He trusted them. He let them in without hesitation. Then he turned his back and walked back to  the stove. That was his mistake.

The visitor pulled out a 22 caliber pistol with a suppressor attached to the barrel. Quiet, professional, the kind of gun you use when you do not want the neighbors to hear. The first shot hit Sam in the back of the head just above the neck. The impact knocked him forward. He crashed into the stove, scattering pots and pans across the kitchen floor.

 Sausages rolled into the corners. Peppers splattered against the wall. Sam was down, but he was not dead yet. The killer stepped closer and kept firing. Six more shots followed. One of them struck Sam in the mouth. In total, seven bullets, each one deliberate, each one placed with precision. The shot to the mouth was the signature.

 It was a message from the mob. You talked too much or you were about to. When it was over, the killer stood there for a moment, looking down at the body of one of the most powerful mobsters in American history. Then the killer wiped down the gun, dropped it on the floor next to Sam’s body, and walked out. No forced entry, no struggle, no witnesses.

Just Sam Gian Kana, the man who had run the Chicago outfit for a decade. The man who had worked with the CIA, the man who had shared a mistress with the president of the United States, lying dead on his kitchen floor in a pool of blood and cold sausage. The apartment door was locked from the inside.

 Whoever killed Sam had a key or Sam had locked it after letting them in. Either way, it did not matter. The killer was gone. Bonnie’s husband found the body the next morning when they came home. He walked into the kitchen and saw Sam lying face down near the stove. He called the police. By noon, Oak Park was swarming with detectives, homicide investigators from the Cook County Sheriff’s Office, FBI agents, reporters, photographers.

Everyone wanted a piece of the story. Sam Mooney Gian Kana, the legendary mob boss, murdered in his own home. By evening, it was the lead story on every news broadcast in the country. The timing was what made it explosive. Sam Gian Kana had been subpoenaed by the United States Senate just days earlier. The Church Committee, officially called the Senate Select  Committee to study governmental operations with respect to intelligence activities, was investigating the CIA’s involvement in assassinations of foreign leaders. And

Sam was one of their star witnesses. He was scheduled to testify on June 24th, 1975, 5 days after he was killed. The committee wanted to ask Sam about Operation Mongoose, the CIA backed plots to assassinate Fidel Castro. They wanted to know about the poison pills, the mob contacts in Cuba, the meetings with CIA handlers.

 They wanted Sam to tell them everything. And Sam would have, not because he wanted to cooperate, but because he was angry. Angry at the government for using him and then throwing him away. Angry at the outfit for pushing him out. angry at the Kennedys for betraying him. Sam had spent his entire life keeping secrets. But now at 67 years old, broke and powerless, he had nothing left to lose except his life.

 The Chicago outfit could not let Sam testify. Tony Aardo, the real power behind the throne, and Joey Aayupa, the current boss, knew what Sam could say. He could talk about the skim from Las Vegas, bribing politicians and judges, murders, extortion, and lone sharking. He could burn the entire organization to the ground.

 More than that, Sam could implicate the CIA. He could describe government agents meeting with mobsters to plot the murder of a foreign leader. He could expose the partnership between organized crime and the United States intelligence community. he could blow open one of the biggest  scandals in American history. So, the decision was made.

 Sam had to go. The hit was clean, professional. Someone Sam trusted walked into his house, shot him seven times, and walked out.  The Oak Park Police Department launched an investigation. They interviewed hundreds of people. They looked at mob figures, CIA operatives, former associates, anyone with a motive. But nobody talked.

Nobody saw anything. The gun had no fingerprints. There were no witnesses. The case went cold almost immediately. The leading theory among investigators was that the Chicago outfit had ordered the hit. Aardo or Aayupa had given the word and someone close to Sam had carried it out. Some detectives suspected Butch Blloy, Sam’s former driver and bodyguard who had been seen in the neighborhood that night.

 Others thought it was Chucky English, another outfit member who knew Sam well. But without evidence, without witnesses, the case was dead. A few investigators whispered about the CIA. What if the agency had decided Sam was too dangerous to testify? What if they had contracted the hit themselves, using mob connections to cover their tracks? It was not impossible.

 The CIA had worked with the mob before. Why not one more time? But those theories never went anywhere. The CIA denied involvement. The mob said nothing and Sam Gianana stayed dead. One week after Sam’s  murder, Johnny Rosselli, his partner in the CIA Castro plots, appeared before the church committee. Roselli told the senators about Operation Mongoose.

 He  described the poison pills, the meetings with CIA handlers, the attempts on Castro<unk>’s life, but he did not tell them everything. He could not. Some of the secrets had died with Sam.  Roselli knew he was next. In July 1976,  13 months after Sam’s murder, Johnny Roselli disappeared. His body was found 10 days later, stuffed inside a 55gallon oil drum floating in Dumbfoundling Bay near Miami.

 He had been strangled, shot, and dismembered. The Mob was cleaning  house. Everyone who knew about the CIA plots, everyone who could testify, everyone who posed a threat, they were all being eliminated. Sam Gianana had believed his secrets would protect him. He thought the outfit would not dare kill him because of what he knew.

 He thought the CIA  would shield him because he had done their dirty work. He was wrong on both counts. In the end, Sam’s secrets made him a target. And in the mob, when you become a liability, there is only one solution. Seven bullets, a quiet kitchen in Oak Park, and decades  of secrets buried with him in an unmarked grave.