The Chicago Mob Boss Who Refused to Die: Sam Giancana Escaped Death for 20 Years

June 19th, 1975, Oak Park, Illinois. Federal agents found Sam Gianana face down in his basement kitchen. Seven bullets in his head arranged in a perfect circle around his mouth and throat. One shot fired up through his chin into his brain. The mob boss, who had stolen  a presidential election, plotted with the CIA to kill Castro, and survived 20 years of betrayals that would have gotten any other gangster murdered, was finally dead.

 The question wasn’t who killed him. The question was how the hell did he stay alive this long. The call came into Oak Park Police Department at 10:43 p.m. A caretaker had found something at 14:30 Winona Avenue. When unformed officers arrived at the modest brick bungalow, they found the front door unlocked. No signs  of forced entry, no signs of struggle.

 Just Sam Gianana, 70 years old, lying on the floor of his basement kitchen in a pool of blood. He was wearing a  bathrobe and slippers. On the stove, sausages were still cooking. A pot of escarole  sat nearby, steam rising. The kitchen table was set for two. Whoever  killed Sam Gianana had been invited in for dinner.

 The crime scene told a story that made even seasoned  homicide detectives uncomfortable. Seven shots to the head, five around the mouth, one under the chin, one in the back of  the skull. Classic mob execution, but the placement  was deliberate, almost ritualistic. The shooter wanted to send a message.

Keep your mouth shut. You talk too much. FBI agents flooded the scene within hours. This was not just any murder. This was the assassination of one of the most powerful organized crime figures in American history. A man who had run the Chicago  outfit. A man who had rigged elections.

 A man who knew secrets about presidents and prime ministers. A man who, for reasons  nobody could quite explain, had been allowed to live far longer than he should have. Special agent in charge Richard Held took control of the investigation. The bureau  had been watching Gian Kana for decades.

 Surveillance teams had followed him to restaurants, casinos, and mistresses apartments from Chicago to Las Vegas to Mexico City. They had wiretapped his phones, bugged his homes, documented his every move. And now, after all those years, somebody had finally gotten to him in his own house while he was  cooking dinner. The initial suspect list was long.

 Suspects included Joey Aayupa, the new boss of the Chicago outfit who had taken over when Gian Kana went into exile. Tony Spelotro, the outfit’s enforcer in Las Vegas, who had learned his trade under Gian Kana. Butch Blazy, Gianana’s longtime driver and bodyguard, the last person seen with him alive, the CIA, which had every reason to silence a man who knew too much about government assassination plots.

 even the FBI itself, though nobody said that out loud. Oak Park Police Chief Roy Olsen held a press conference the next morning. Reporters asked the obvious question, “Who killed Sam Gian Kana?” Olsson said they were pursuing several leads. Then he added, “But let’s be honest, this is a mobby hit, and mob hits do not get solved unless somebody talks.

” In this case, the only man who could have talked was lying on a slab in the Cook County Morg with seven bullets in his head. The autopsy confirmed what everyone already knew. Cause of death, multiple gunshot  wounds to the head. Time of death: approximately 1000 p.m. The shooter used a 22 caliber pistol, probably equipped with a  suppressor. No neighbors heard gunshots.

No witnesses saw anyone enter or leave the house. Professional work, outfit work. But here is what bothered investigators. Sam Jan Kana had been marked for death for 20 years. The outfit  does not wait that long. When you are a liability, when you bring heat, when you betray the organization, you get whacked  fast, clean, final.

 So why did Jian Kana get two decades? What kept him alive when everyone, the mob, the government, and his own former friends wanted him dead? To understand how Sam Gianana survived so long, you have to understand  who he was and how he got there. He was born Salvatore Jangana on June 15th, 1908 on the west side of Chicago. His parents  were Sicilian immigrants.

 His father drove a push cart. The family lived in a tenement in the patch, the Italian ghetto near Taylor Street. Young Sam, they called him Mooney, short for Momo, which meant crazy. Crazy in Italian. and he earned that nickname. By the time he was 10, Mooney was stealing  cars. By 15, he had joined the 42 gang, the most vicious crew of juvenile delinquents Chicago had ever seen.

 These were not kids playing gangster. These were stone cold criminals. They hijacked trucks. They robbed stores. They beat people to death with baseball bats for looking at them wrong. The 42 gang was a farm team for the Chicago Outfit. If you survived it, if you proved yourself ruthless enough, you got  made. Gian Kana proved himself over and over.

He was arrested dozens of times for burglary, autotheft,  assault, murder. Nothing stuck. Witnesses disappeared. Cops got paid off. Judges looked the other way. By the time he was in his 20s, Mooney had  killed his first man, maybe his second and third, too. Nobody kept count.

 What mattered was that he had ice in  his veins. He did not hesitate. He felt no remorse. He did what needed to be done. In the 1930s, Gianana came to the attention of Paul the waiter, Ra, and Tony Joe Batters, Aardo, the two men who really ran the Chicago outfit. Al Capone was in prison.

 Frank Niti was the front man, but Ra and Dicardo were the brains. They saw something in Gianana. Intelligence, ambition, and a willingness to get his hands dirty. They brought him into the organization. They gave him a crew. They taught him how the outfit worked, policy wheels, bookmaking, lone sharking, extortion, and most importantly,  how to avoid prison.

Gian Kana ran gambling operations on the south side. He controlled the black policy rackets, the numbers games that brought in millions. He was smart. He kept detailed  records, then destroyed them. He never talked on the phone. He met people  in public places where bugs could not be planted.

 He paid off cops, judges, aldermen, anyone with power. And when someone crossed him, he eliminated them quickly, quietly. By the late 1940s, Gian Kana was one of Aardo’s  top lieutenants. When Aardo stepped back from day-to-day operations in 1957, he chose Gian Kana to be the boss. Not the boss in name, Aardo and Ra still called the shots from behind the scenes, but the boss in practice.

 the guy who ran the meetings, the guy who gave the orders, the guy who took the heat. And Gian Kana took a lot of heat. Because unlike Aardo, who lived quietly in River Forest and played golf, Gian Kana loved the spotlight. He dated celebrities. He hung out in nightclubs. He flew to Las Vegas and stayed in suites at the Desert Inn in the Sands.

He became friends with Frank Sinatra, Dean Martin, Sammy Davis Jr., the whole rat pack. He was seen, he was photographed, he was talked about, and the FBI noticed. By 1960, the bureau had Gian Kana under constant surveillance. Agents followed him  everywhere. They sat outside his house. They tailed his car.

 They photographed everyone he met with. Gianana hated it. He complained to lawyers. He sued the government for harassment. He even confronted agents on the street, taunting them,  asking them why they were wasting taxpayer money following him when he was just a simple businessman. But Gian Kana wasn’t a simple businessman.

He was the boss of the most powerful criminal organization in America. And in 1960, he was about to make a deal that would protect him for the next 15 years. A deal with a future president. The story starts in the late 1950s at a hotel in Chicago. Joe Kennedy, father of Senator Jack Kennedy, sat down for a meeting with Sam Gianana.

 Joe Kennedy wanted his son to be president. But there was a problem. The 1960 election was going to be close. Richard Nixon was popular. The Republican machine was strong. And the Democrats needed every vote they could get. Especially in swing states like Illinois. Joe Kennedy knew people.

 He had made his fortune during prohibition, smuggling whiskey, working  with bootleggers, men like Gian Kana. And now he needed a favor. Could Gian Kana use his connections, his control over labor unions, his influence in Chicago’s wards to swing the vote for Jack Kennedy? Jan Kana said yes. But there was a price. If Jack Kennedy became president, the outfit would have the ear of the White House.

 the federal heat would ease up and Bobby Kennedy, who had been tearing into mobsters during Senate hearings, would back off. That was the deal. Gianana went to work. He sent his soldiers into Chicago’s Italian and Irish neighborhoods. He told them to get out the vote. Talk to the old grease balls, he said. Talk to the Pocks. Tell them Kennedy is good for us.

Tell them to vote. And if they need convincing, convince them. The outfit controlled unions, teamsters,  laborers, service workers. Gianana had precinct captains  on his payroll. He had pole workers ready to stuff ballot boxes if necessary. Election night 1960. The race was razor thin.

 Nationally, Kennedy won by onetenth of 1%. But in Illinois, Kennedy won by only 9,000 votes. 9,000 votes in a state where Gian Kanda controlled entire wards on the  south side and west side of Chicago. Did Gian Kana steal the election for Kennedy? Nobody knows for sure, but Gian Kana believed he did. And that belief kept him alive.

 Once Kennedy won, Gian Kana  expected the heat to ease up. He expected Bobby Kennedy, now attorney general, to lay off. Instead, Bobby Kennedy declared war. He launched a massive crackdown on organized crime. He authorized wiretaps.  He expanded the FBI’s organized crime division. He personally targeted Gianana, Hawa, Marello, Trafocante, every major mob boss in the country.

 The Kennedys had double crossed the outfit. In the mob, betrayal gets you killed immediately. But John Kana did not get killed. Why? because he had insurance, he had proof of the deal, he had connections to  the Kennedys that went beyond Pos’s own politics. He was sleeping with the same women as Jack Kennedy.

 Judith Campbell Exner, a beautiful brunette, was Gian Kana’s girlfriend. She was also Jack Kennedy’s mistress. Gian Kana knew about the affair. He used it. If the Kennedys went after him too hard, he would go public and destroy the presidency. But there was something else protecting Sam Gian Kana.

 Something even more dangerous than blackmail. The Central Intelligence Agency. In September 1960,  before Kennedy even won the election, the Central Intelligence Agency approached the mob with a proposal. Fidel Castro had taken over Cuba. American businesses, including mob owned casinos, had been nationalized. The agency wanted Castro dead, but they could not  do it themselves.

 Too messy. Too much risk of exposure. So, they went  to the people who killed for a living, the mafia. The CIA contacted Johnny Roselli, a mob figure in Los Angeles with ties to the Chicago outfit. Roselli brought in Sam Gianana. The agency offered Gianana $150,000  to organize Castro’s assassination.

Jan Kana agreed not for the money, for the protection. If the CIA needed him, the CIA would protect him. Jana recruited Santo Trafocante Jr., the Tampa boss who had run casinos in Havana before Castro took over. Together, they hatched plans. Poison pills to slip into Castro’s food, poison cigars, even poison diving suits. None of it worked.

Castro’s security was too tight. Every meal was tested by political prisoners. Every cigar was  inspected. The plots failed. But the relationship between Gianana and the CIA continued. And that relationship became Gianana’s shield. Because now the FBI  had a problem. They wanted to prosecute Gianana. They had wiretaps.

 They had evidence. But every time they got close, the CIA stepped in. The agency said they needed him. He was working on a matter of national security and you could not touch him. The FBI was furious. Jay Edgar Hoover hated the CIA. He hated being told what to do. But the CIA had leverage. They had the Kennedy administration’s backing.

 And Gian Kana walked. FBI surveillance records from 1961 and 1962 show constant frustration. Agents documented Jan Kana’s meetings with Roselli, with Trafficante, with known assassins. They knew something was going on, but when they tried to move on it, they got shut down. One FBI memo from July 1962 reads, “Subject Jan Kana continues to operate with apparent impunity.

 Attempts to pursue investigation blocked by agency interference. recommend direct confrontation with Attorney General, but Bobby Kennedy could not confront the CIA without exposing his brother’s connection to the Castro plots. The whole thing was a mess. And in the middle of it, Sam Gianana was untouchable.

 He continued running the outfit. He continued making money. He continued living large. And he continued surviving. By 1963,  the outfit was getting nervous. Gian Kana was too visible. He was bringing too  much heat. The FBI was camped outside his house. Agents were following him to golf courses, to restaurants, to his girlfriend’s apartment.

Every move he made was documented. And when you are trying to run a criminal enterprise, that kind of attention is bad for business. Tony Aardo called a meeting. He told Jon Kana to cool it. Stop being seen  with Sinatra. Stop going to Vegas. Stop sleeping with celebrities. Lelo. Gianana refused.

 He liked the  spotlight. He liked the power. He liked feeling important. And besides, he had protection. The CIA needed him. The Kennedys could not touch him. What could the outfit do? Then on November 22nd, 1963, President Kennedy was assassinated  in Dallas. And everything changed. After Kennedy’s death, John Kana’s CIA  protection started to evaporate.

The Castro plots were being quietly shut down. The agency did not need him anymore, and the FBI, unleashed from political interference, came after him hard. In 1965, Gianana was called before a federal grand jury investigating organized crime. He refused to testify.  He took the fifth amendment on every question.

 The government offered him immunity, which meant he could not incriminate  himself, which meant he had no legal reason not to talk. He still refused. Judge Richard Austin found him in contempt and sent him to Cook County Jail. Gianana spent a year behind bars, not in general population. He was kept in protective custody, isolated from other inmates.

 The outfit was worried. What if Jana talked? What if he cut a deal? What if he gave up Aardo, Ra, Aayupa, the whole leadership? But Djangana kept his mouth shut. He did his time. And when he got out in May 1966, he made a decision. He left the country. Junkana flew to Mexico and settled in Quavaka, a resort town 50 mi south of Mexico City.

 He bought  a villa. He lived quietly. He golfed. He entertained visitors. and from Mexico. He continued to run outfit operations in Chicago. Money was couriered to him. Orders were sent back. He stayed in control, but his exile frustrated the organization. Joey Aayupa had taken over day-to-day operations while Gianana was gone.

Aayupa was steady. He was careful. He did not make waves. And he did not want Gianana coming back and causing problems. The outfit’s patience was wearing thin. Mexican authorities pressured  by the US government kept tabs on Gianana. His phone was tapped. His movements were monitored. In July 1974, Mexican officials arrested him and put him on a plane to San Antonio, Texas.

After 8 years in exile, Sam Jana was back in the United States. The FBI was waiting. So was a federal grand jury. So was the Senate Select Committee on Intelligence, better known as the Church Committee, which was investigating CIA abuses, including the Castro assassination plots. Gian Kana was subpoenaed to testify, and this time there was no running.

 Jana returned to his home in Oak Park in July 1974. The house at 14:30 Winona Avenue was modest  for a mob boss. Brick bungalow, small lawn, basement, kitchen. He had bought it years earlier under his daughter’s name to avoid seizure. Now it was the only place he had left. The church committee wanted him to testify about the CIA’s relationship with the mafia, about the Castro plots, about what he knew.

 And Gian Kana knew everything. He knew about the poison pills. He knew about the meetings with agency operatives. He knew about Johnny Roselli’s role. He knew about the Kennedy  connection. He knew too much. His lawyer advised him to cooperate, cut a deal, tell the committee what they want to know, stay out of prison. But Junk Conana refused.

He was not a rat. He had kept his mouth shut for  50 years. He was not going to start talking now. Not to Congress, not to anyone. The outfit heard about the subpoena. They heard Gian Kana was being pressured to testify and they made a decision. Jana had been a liability for years. He had brought heat. He had been too visible.

 He had made too many enemies. And now he was about to sit in front of a Senate committee and possibly spill secrets that could bring down the entire organization. He had to go. The order came from the top. Joey Aayupa and Tony Cardardo, the old men who ran the outfit from the shadows. Gian Kana would be eliminated.

  The question was who would do it and when. In the weeks before his death, Gian Kana knew something was wrong. He told his daughter, Antwanette, that he felt like he was being watched. Not by the FBI, by the outfit. He said he did not trust anyone anymore. Not his friends, not his bodyguards, not even his driver, Butch Blloy, who had been with him for decades.

On the night of June 19th, 1975, Gian Kana was home alone. His caretaker, Joseph Dersio, had left for the night. Gianana’s daughter was in Las Vegas. He was  cooking dinner, sausages, and escarole. Someone came to the door, someone he knew, someone he trusted enough to let into his house,  someone he was cooking for.

 That someone shot him seven times in the head. The investigation into Sam Gianana’s murder was doomed from the start. No witnesses, no forensic evidence, no murder weapon, just a body and a list of suspects that read like a who’s who of organized crime. The prime suspect was Butch Blloy, Dominic Blossi, John Connor’s driver and bodyguard for over 20 years, was with him the day of the murder.

 They had been to a doctor’s appointment together. They drove back to Oak Park. Blossi said he dropped Jon Kana off around 6:00 p.m. and went home. But witnesses said they  saw Blossi’s car parked near Jon Kana’s house later that evening. Blloi knew the house. He had a key. He knew Jana’s routines. And most importantly, Jana would have let him in without question.

You do not survive 50 years in the mob by being paranoid about your driver. You trust him, and that trust can get you killed. FBI agents brought Blloy in for questioning. He denied everything. I was not there, he said. I went home. I did not see Sam again  after I dropped him off. Agents pressed him.

They showed him witness statements. They told him about the car. Bllyi did not budge. He took a polygraph test. The results were inconclusive. Without physical evidence, without a confession, they could not charge him. Another suspect was Tony Spelotro. Tony the Ant, the outfit’s enforcer in Las Vegas. Spelotro had learned his trade under John Kana. He had killed for him.

 He had worked for him. But by 1975, Spelotro was answering to Joey Aayupa, not Gian Kana, and Aayupa wanted Gian Kana dead. Did Spelotro fly to Chicago, do the job, and fly back? It is possible. Spelotro was capable. He was vicious. He beat men to death with his bare hands. But there is no evidence he was in Chicago that night.

 Some investigators believed  it was a team. That Blossi let the shooters into the house then left. That two or three men, maybe outfit soldiers from Chicago, did the actual killing. The seven shots suggest professionalism. The placement around the mouth and  throat suggests a message. Keep quiet. Do not talk.

 Classic mob symbolism. There is also the CIA theory that the agency worried about what Gian Kana might tell the church committee sent their own people to eliminate him. This theory gained traction when Johnny Rosselli, who worked with Gian Kana on the Castro plots, was murdered a year later.

 Roselli’s body was found stuffed in an oil drum floating  off the coast of Florida. Roselli had also been subpoenaed by the church committee. He testified and then he was killed. The timing was suspicious, but most investigators believe it was an outfit hit,  pure and simple. Gianana had become a liability. The organization voted, the order was given, and somebody close to him, somebody he trusted, carried it out.

The Oak Park Police Department officially closed the case in 1977, unsolved. The FBI kept it open for years, but no arrests were ever made, no charges filed. Butch Blloy lived until 2004. He died  of natural causes, never charged, never convicted. Tony Spelotro was murdered  in 1986, beaten to death in a basement in Bensonville, and buried in an Indiana cornfield.

 He never talked about Gian Kana. Joey Aayupa went to prison in the 1980s on raketeering charges. He never talked either. Tony Aardo died in 1992 at age 86 peacefully in his bed. He took whatever he knew to  the grave. The sausages were still on the stove when police arrived. The escarole was still warm.

 The table was set for two. Gianana had been cooking for  someone he knew, someone he trusted. Someone who put seven bullets in his head and walked out the door like nothing happened. That is how the mob works. You trust the wrong person. You live too long. You know too much. And one  night while you are cooking dinner in your basement, it all catches up with you.

 Sam Gian Kana survived 20 years longer than he should have. He survived because he had leverage, the Kennedy connection, the CIA protection, the secrets he kept locked in his head. But in the end, none of it mattered because the Emma does not forgive. The Emma does not forget. And when you become more valuable dead than alive, you die.

 Gianana thought he was untouchable. He thought his connections would save him. He thought the outfit needed him. He was wrong. On June 19th, 1975, in a basement in Oak Park, Sam John Kana learned what every mobster learns eventually. Nobody is untouchable. Nobody is indispensable.  And nobody escapes forever.