Sam Giancana: Secret Ties Between the Mafia and the White House | Rogues Gallery JJ

Sam Giancana was one of the most powerful mob bosses in the 20th century. He was also the most scrutinized gangster  in FBI history. Both FBI Director J. Edgar Hoover and Attorney General Robert Kennedy became  obsessed with netting the Chicago mobster. They used every trick in the book including illegal wiretaps, bugs,    and 24-hour surveillance. Giancana fought back. The Chicago Outfit didn’t like publicity, but Sam ignored  their warning. He’d worked hard to get to the top. Now

he would do as he pleased, or so he thought. Sam Giancana enjoyed being in the spotlight. Let everybody know that at that time he was the Capo de Capi of the Chicago Crime Syndicate. Sam Giancana might have had a pretty big ego that made him enjoy all the attention he called on himself by either dating Phyllis McGuire or running around with the Rat Pack or maybe sharing a mistress with John F. Kennedy. He was mean. He was vindictive. He had no problem gaining revenge any way possible. He killed people.

Sam Giancana was a psychopath. He had really no conscience. Uh The definition of a psychopath is someone who knows the difference between right and wrong, but just doesn’t care. And that was Sam Giancana.      Rogue’s Gallery is narrated by William Devane. This episode,  Sam Giancana. The year is 1943.  America is deeply engaged in World War II.  Movies have a patriotic tone. There are shortages of everything from food to  gasoline.

No one much notices when 35-year-old gangster Sam Giancana leaves Terre Haute prison in Indiana after a 4-year stretch for bootlegging. He goes home to his family in Chicago, an obscure small-time hoodlum with big plans for his future. The Chicago Outfit, as the mob is known locally, has a new boss, Tony Accardo.  Sam wants to make a good impression on Accardo, but how? A prison  contact has planted an idea in Giancana’s head. Apparently while Sam Giancana was in prison in Terre Haute,

he met Eddie Jones who was    with his brothers, they were the biggest black policy operators in Chicago. A policy operation is the same thing as a numbers racket, basically an illegal lottery. A person picks a combination of numbers, and if his numbers come up, he wins. The Chicago Outfit has always shunned the black policy rackets, thinking there was no real  money involved since players bet only a few cents at a time. But Giancana  has learned otherwise. Eddie Jones started sharing the

information with them on what policy is, how much it makes, how is it run. He became aware that this was not a nickel-and-dime operation, that there were tremendous sums. Eddie set Sam up with his own joint, the Boogie Woogie Club. From there, Giancana launches his own policy  racket for the Outfit. Eddie Jones might have been thinking that, you know what I’ll be doing here, I’ll be taking an insurance policy. I’ll cooperate a little bit with these guys, and then we can all get along. But

there’s a real difference between feeding a tame dog and trying to feed a rabid dog. The rabid dog just bites your arm off. And that’s essentially what Sam Giancana did. When Sam sees the policy  rackets pull in millions of dollars, he doesn’t want to share anymore. He kidnaps Eddie and threatens to  kill him if he doesn’t hand over the policy business. Jones, knowing Giancana  will make good on his threats, takes his family and leaves Chicago for good. Sam Giancana is on his way up.

When you come up with an idea that produces a lot of money for the mob, you’ve done yourself a very good turn, and you’re going to be a rising star in the mob. If you’re bringing policy money into the mob, you’re suddenly a lieutenant. You’re suddenly a a boss. Sam uses his profits to invest in other enterprises, a trotting club, a shrimp exporting business in Cuba, casinos and lounges that front gambling clubs. They are all money makers. Once Sam Giancana started rising in the

mob, like all mobsters, he wanted the better things in life. So what he did then was he moved out of Chicago and moved to a suburb of Oak Park, built a reasonable-size, nice home, not gaudy or ostentatious. Cloaking himself in respectability, Sam favors the traditional Italian lifestyle. He demands that his family  do the same, ignoring the fact that his wife, Angeline, is in fragile health. He treated his wife  basically like a scrub woman, a person who kept the house and kept it clean, and when

they came home at midnight and wanted pasta or or sausage and chickpeas, she got out of bed and made it for them. That’s what you did when you were an old-world Italian wife. Sam likes being top dog at home and wants that same power in the Outfit. Giancana is making big money for the organization, and he’s growing tight with mob leader Tony Accardo. It’s 1956. All of Sam’s ambitions are about to pay off. Sam Giancana was ruthless, a megalomaniac, and he wanted to be the top dog.

Eventually Accardo decided that he wanted to step down as day-to-day operating boss. It puts a lot of wear and tear on a guy and just recede to be the chairman of the board. Giancana became the boss by bringing in the goods, by running his crews, by overseeing gambling, by simply doing what the mob had to do to bring in cash. Accardo trusted him. Sam Giancana liked to be number one. He let everybody know that at that time he was the Capo de Capi of the Chicago Crime Syndicate. But what price is Sam  Giancana

willing to pay to be the boss? Little does he suspect the price might be too steep even for him. Sam Giancana takes over as leader of the Chicago Outfit in 1956.  Within a year, the FBI makes him their number one target. G-men work outside  the law using bugs and wiretaps for which they have no warrants. Giancana is unaware that even his love trysts are grist for the  mill of the FBI’s relentless spying. Sam Giancana  came into the mob as the boss of the mob at the absolute

worst time when the FBI decided to intensify surveillance of organized crime, and he took a lot of the heat. Up until 1957, FBI Director J. Edgar Hoover had strongly denied that there even was an organized crime syndicate in America. One of the things that J. Edgar Hoover never wanted his agents to do was to um cultivate informants. And in order to get into the mob, you had to have informants. You had to have people who were double agents, who would go both ways for you. Hoover never wanted that. He felt his

agents could be corrupted. But a meeting of mob bosses forces Hoover’s hand. The Apalachin  Conference was a meeting and where all the leaders of organized crime met up in Apalachin, New  York, and a very observant state trooper was paying attention  to all the fancy cars going up to this estate, and raided it. And at this like conclave was, you know, 50 or 60 or so organized crime  figures from all over the country, and obviously they were meeting there for some reason. A number of top

organized crime figures were captured at Apalachin. A number of other ones fled into the woods and got away. Reportedly, Sam Giancana is one of the ones that could run fast, and he just got out of there. This was the first evidence that there was a national group of mobsters who actually talked to each other. This showed it to be a national problem, and Hoover didn’t know anything about it. He was embarrassed because of course J. Edgar Hoover was the great crime fighter. Hoover quickly organizes the Top 

Hoodlum program to collect information. He dispatches agents throughout the  country. No judge will authorize covert surveillance techniques without evidence of wrongdoing. Hoover doesn’t  care. He orders illegal wiretaps and bugs. Agents place an eavesdropping device  at Sam’s favorite meeting place, the Armory Lounge, where he conducts most  of his business. They planted microphones indiscriminately, anywhere they could. They did anything they could. Violated

every just about every constitutional right to privacy law that existed. I don’t think the uh, Chicago mob including Sam Giancana ever knew at the time that the FBI was listening in on them. Sam Giancana, of course, was aware of the physical surveillance. He could see FBI guys parked outside of his house or in the alley in the back. Could see them following him around. Sam Giancana took the majority of the uh, surveillance pressure,  no doubt. But from the microphones, they quickly learned that he was actually the

day-to-day operating boss and he became the number  one target. Giancana has brought some of this unwanted attention on himself. His high-profile lifestyle invites publicity. The Outfit  does not approve. Sam Giancana was a playboy. And he was the first playboy gangster that we ever had. Uh, it’s well known that his girlfriend was Phyllis McGuire of the singing McGuires. Sam has a lot of Hollywood stars who are close  friends. One is Frank Sinatra. Among the many stars that Sinatra

introduces to Giancana are Marilyn Monroe and Peter Lawford, the brother-in-law  of Senator John Kennedy, as well as Sinatra’s friends in the Rat Pack. Well, the Rat Pack loved gangsters. They were part of the Las Vegas gangster crowd. They like to go to party with them. They loved the babes. They loved the whole scene. And so, the more the merrier and Giancana was certainly part of that.  [laughter]  How do you feel about all this publicity? Would you turn around and let

us have that smile this direction?  pretty good. Like you lost a little weight. You’ve been playing a lot of golf? The mob of Chicago did not do that type of thing. They were not a flamboyant Hollywood boutique mob. They took care of business. As he was flaunting his power and flaunting his his fame and notoriety and bringing a lot of heat on the mob. Sam Giancana’s closest ties are allegedly with Frank Sinatra. An often repeated yet never proven tale might explain this. It’s said that bandleader

Tommy Dorsey  forced 20-year-old Sinatra to sign over 35% of his lifetime earnings in order to get his big break. When Sinatra wanted to leave the band a year later, Dorsey refused  to nullify the contract. The big rumor in Chicago to this day is that Sam Giancana is the guy that got him out of the Dorsey contract. That’s what everybody believes is that it was Sam Giancana that made the necessary arrangements. That’s not the only story that links Frank Sinatra  and Sam Giancana.

The crooner’s career was in a slump because of throat problems. During this period, Sinatra really wanted the part of Maggio  in From Here to Eternity. But Harry Cohn, the president of Columbia, didn’t want him for the part. So, Giancana  put pressure on Cohn to audition Sinatra. He not only got the part but won an Oscar and established a new career as a serious actor. Isn’t it exciting now? Just great. It’s just wonderful. We’re both very thrilled, I’m sure.

Chicago mob seemed to have a very close working relationship with those guys where they expected guys like Sinatra, Martin, Sammy Davis Jr. to  work Vegas for them at scale, at low rates. And in fact, at one point in time, um, they were overheard, the Chicago mobsters were overheard being  on a FBI, um, bug, being quite displeased with these guys for not holding up their end of it. I think it was Sam Giancana who suggested that we, quote, put that one-eyed little nerd against the other

eye out, unquote. As a way of sending  a message to these guys. Sam’s much cherished wife, Angeline, dies  suddenly in 1954 of a cerebral embolism at the age of 45. His mourning, though genuine,  is brief. Sam likes beautiful women and it flatters his vanity to be seen with them. His most famous liaison, and the one that gets him in the  most trouble with the mob, is with Phyllis McGuire of the McGuire Sisters. What the attraction there was, God only knows, cuz Giancana was certainly not a

Lothario. He was kind of a homely mutt. Uh, Phyllis was an attractive, uh, popular, um, woman. Why the two linked, why the chemistry was there, McGuire was crazy about him. Has your association with Giancana in the past hurt your career, do you think? Uh, I’m very warm. It’s very warm here. Where are you going now? It wasn’t a good career move for uh, either Sam Giancana or Phyllis McGuire probably to have uh, the relationship they had. Phyllis McGuire was America’s sweetheart and now she’s seen running around with a

known gangster. By running around with um, one of the most well-known entertainers of that day, he called all kinds of attention on to himself. The FBI follows them everywhere, taking pictures, bugging hotel rooms, tapping phones. Sam is annoyed by all the attention that he and Phyllis attract. The Chicago Outfit is annoyed, too. Former boss Tony Accardo  warns Sam that such publicity can only bring trouble. Giancana ignores the warning. You have to remember that when a mobster like Sam Giancana  gets as

powerful as he got, where he was uh, being paid tribute by other mobsters, where he was running the Outfit and on a day-to-day basis, you get a sense that you’re all powerful, that you’re inviolable, that you’re bulletproof, that you can just about do anything. Giancana was a different kind of guy. He wanted to be let everybody know who Sam was. And the whole world found out about him. It was probably a little embarrassing to the mob, but the reward to the mob was that Giancana was running a machine that

generated a lot of money. You know, money’s salves over a lot of wounds. When Phyllis McGuire is forced to testify at a grand jury hearing on organized crime in May 1965, it marks the beginning of the end of their affair. I really don’t know. Could you tell us where you’re going?  No comment. You know, he said over the weekend that he was pretty angry with you. Did you talk to him about it? No comment. Is this an indication, do you think, that their relationship is all over? No comment. Months after she is

forced to testify, Phyllis breaks off with Sam for good. Hoover continues to stalk Giancana. But the man about to become Hoover’s boss will put on even  more pressure. Robert Kennedy, the new Attorney General under his brother JFK, will soon become Giancana’s  sworn enemy. Many speculate that going up against Sam Giancana may have proved a fatal  mistake for the Kennedys. I want to express my uh, gratitude to uh, my dog Freckles who’s been maligned. I don’t care what they

As Franklin Roosevelt said, I don’t care what they say about me, but when they start to attack my dog, And I it’s not I’m not doing this in the order of importance, but I also want to thank my uh, WIFE, ETHEL.  [screaming]  MY THANKS TO ALL OF YOU AND NOW IT’S ON to Chicago and let’s win there. Robert Kennedy never made it to Chicago, home of the crime boss he tried to destroy in the early ’60s. But ever since RFK’s assassination, there’s been speculation that Sam Giancana had a hand

in it. The connection between Giancana and the Kennedys begins many years earlier when both Joseph Kennedy and Giancana are in the bootlegging  business, though they don’t know each other. They share a common interest, getting ahead. During Prohibition, Sam Giancana  grows up in a tough Italian neighborhood in Chicago called The Patch. There he joins its most notorious street gang, the 42s. They terrorized people. They beat up on each other. They were basically punks. The gangsters of the ’50s, the Giancana

Outfit, uh, you can look back at the 42 gang and they were all buddies. Giancana earns a reputation as the cruelest, most ruthless of the bunch. He kills a man who refuses to pay extortion, then kills the one witness who’s willing to testify.    People in the neighborhood learn to fear Sam Giancana.  As Sam rises  to power in the ’40s and ’50s, Joe Kennedy’s sons, John and Robert, begin making their foray into national politics. Giancana’s first contact with Bobby

 sets up an ominous tone. They clash when Robert Kennedy joins the McClellan Commission in 1957  as its chief counsel. Uh, we are looking into gangster infiltration into labor and management. We will be concentrating on that in this coming year in connection with the Teamsters Union. Labor racketeering has  always been a source of both tremendous wealth and power to the mob. Labor racketeering and the mob were made for each other because it’s muscle. It’s basically tough guys saying, um, “Deal

with us or we’ll shut you down.” It’s fairly easy for the mob to infiltrate labor. They only have to target several top men in the union to gain control. And if the individual didn’t go along with it, uh, they were going to shoot him in the back of the head. Uh, or kill his family, or burn his house. With the blessing of Sam Giancana and other mob bosses, Detroit Teamster leader Jimmy Hoffa is chosen as president of the International Brotherhood of Teamsters in 1957. Robert Kennedy’s first target at the

McClellan hearings is Hoffa. And people under your jurisdiction, you’ve got people in Detroit, at least 15 who have records. You’ve got Joey Glimco in Chicago. I say you’re not tough enough to get rid of these people, then. The Teamsters Union in the 1960s was very heavily tied to organized crime, which was I think the the prime reason that the Bobby Kennedy in the Kennedy administration went after Jimmy Hoffa. When Giancana appears at the McClellan hearings on June 8th, 1959, he carefully invokes the Fifth Amendment

36 times.  to answer because I honestly believe my answer might tend to incriminate me.  tell us anything about any of your operations, or you just giggle every time I ask you a question? I decline to answer because I honestly believe my answer might tend to incriminate me.  I thought only little girls giggled, Mr. Giancana. Huh?  I decline to answer, Father. Will you tell us anything about your operations? I decline to answer because I honestly believe my answer might tend to

incriminate me. Though Giancana hides his anger, he never forgets the insults that Kennedy slings at him during the hearing. This is not the only connection between Sam and the Kennedys. In the mid-50s, presidential hopeful John Kennedy    spends time relaxing on the West Coast. There, JFK meets his brother-in-law  Peter Lawford’s friends, Frank Sinatra and his Rat Pack. Sinatra introduces Kennedy  to many beautiful women, including Marilyn Monroe and Judith Campbell Exner.

JFK becomes involved with Exner, having no idea she’s also the lover of Sam Giancana. Ironically, the JFK 1960 presidential campaign will forge yet another link to Sam Giancana. When Joe Kennedy allegedly appeals to Sam for money  and votes from the mob-dominated Chicago wards. In exchange, Sam expects the Justice  Department to back off the outfit if JFK wins. There’s allegations  that the election was stolen in Illinois for Jack Kennedy, and that was the first thing

that put Jack Kennedy over the top. I used my money to go into the various precincts to get people to vote for Kennedy in Illinois, which was crucial to his election. And so, my fellow Americans, ask not what your country can do for you, ask what you can do for your country.  [cheering]  Now, Sam was thinking more about what his country could do for him. After helping to put the Kennedys in the White House, Giancana thought it would just be a matter of time. But things didn’t work

out that way, not at all. I think it backfired on them to a great extent because the Kennedys became their own people. Certainly Bobby Kennedy did. Bobby Kennedy was the biggest thorn in the side of organized crime of any politician that came along. Then he recognized the danger to America from the literally uncontrolled operations of organized crime, the corruption of of city government, of of law enforcement, of judiciary. The FBI agents who were assigned to go after Sam Giancana found an ally in

Bobby Kennedy. They loved him. And they had carte blanche, free reign to make Sam Giancana’s life miserable, and they did it. J. Edgar Hoover continues to personally head up the revitalized investigation of the mob. While reviewing FBI surveillance reports, Hoover notices a disturbing entry. They discovered telephone calls which were being made from Sam Giancana’s residence in Oak Park to the White House. Director J. Edgar Hoover talked with directly with the President John F. Kennedy and advised him that Judith

Exner was the girlfriend of Sam Giancana, the boss of the Chicago organized crime syndicate. And shortly after that confidential conversation, President Kennedy broke it off with her. Sinatra also gets the brush-off from the Kennedys, so Giancana is left out in the cold, feeling both angry and extremely used by the two brothers. Worse is to come. Now, the new Attorney General makes getting Giancana a top priority. When the FBI really turned up the heat on Sam Giancana, they switched from occasional physical surveillance to

around-the-clock lockstep, 24-hour surveillance of Sam Giancana. They knew that this is a guy who couldn’t take that sort of pressure and was likely to crack under that sort of pressure. It was really harassment. It was aggravating, and it really did bother Sam Giancana. It infuriated him. It was basically the type of thing I don’t think they could get away with today. Sam couldn’t take it. He lashed out. Sam Giancana ultimately sued the FBI because of the harassment and actually got a restraining order against the FBI

agents so that they couldn’t do certain things. The publicity generated as a result of this trial, which brought screaming headlines in the newspapers of the of the day, focused attention on Sam Giancana and his antics. That was I think all part of his downfall. That’s the way he did business. To hell with you, stick my fist in your face type of thing. That’s the way he confronted his problems, and in many respects, he was an anathema to the low-key Chicago mob. Though Tony Accardo has retired from

active duty,  he’s still the titular head and wields power within the outfit. Had Accardo known that Giancana would actually dare to take on the FBI, he would have warned against it. In the aftermath of Robert Kennedy’s assault on Sam Giancana, many have questioned the possibility of the mob’s  involvement in the deaths of President John F. Kennedy, Marilyn Monroe, and Robert F. Kennedy. One theory contends  that the outfit believed if JFK was no longer president, Lyndon Johnson would quickly

remove Bobby  Kennedy from power. On November 22nd, 1963, President John F. Kennedy is assassinated. The suspect, Lee Harvey Oswald, is a man with  a troubled past. The next morning, as Oswald is being moved to a different jail, a gunman springs  from the crowd and shoots Oswald point-blank in the stomach, despite heavy security at the scene.    Jack Ruby, who shot and forever silenced Kennedy’s alleged assassin, has rumored ties to the mob. Jack Ruby as a nightclub owner might

have had some tenuous links to organized crime in Dallas,    but I think it’s a long way from here to there. Mobsters don’t hit politicians by and large unless they get severely double-crossed by these people, just as they don’t hit police officers for doing their job. I’ve never seen credible evidence that the mob had the will to get rid of a national leader like that. They knew that if you did something like that, you were basically signing your death warrant.

When Bobby Kennedy got close to returning to power on a presidential level, he, too, was killed. The case has been made that the mob was afraid to see Bobby back at the helm, where he might once again turn up the heat on them. The assassination of Bobby Kennedy, again, I think they benefited tremendously from it. They were not unhappy that he was assassinated. It was definitely to their advantage. Many conspiracy theorists suggest New Orleans boss Carlos Marcello was behind the assassination because of his

personal grudges with Bobby. They contend that Marcello would have received official  approval from other bosses like Giancana to go ahead with the hit. Obviously, a lot of mobsters didn’t like Robert F. Kennedy. Carlos Marcello might have spoken out of turn once or twice in anger and said, you know, damn it, I you know, I’m going to get that guy if it’s the last thing I do, but I think all of us have said things like that about somebody in anger. That doesn’t mean that we eventually arrange for their

killing. What about Marilyn Monroe, whose cause of death is officially listed as an accidental overdose? For instance,  it’s been suggested that the Chicago mob through Giancana had Marilyn Monroe killed to get back at the Kennedys. Well, you can suggest whatever you want to, but if there’s no hard evidence, then it’s just idle speculation. Whatever the truth, Giancana does not ignore mob  business during the 1960s. He oversees the expansion of the Chicago outfit. He travels all over the

world, and amazingly, at the same time that one agency of the U.S. government is dogging Sam’s every move, another agency enlists his criminal expertise in a secret campaign against an enemy  government.    It’s late at night. G-men have slipped inside  the Chicago outfit’s favorite meeting place, the Armory Lounge.    We’re back in the early ’60s, when surveillance on Sam Giancana is at its most intense. Agents discover a cache of sophisticated

eavesdropping devices. But these aren’t the FBI’s bugs and This box of equipment belongs to the Central Intelligence Agency. What possible connection could there be between  Sam Giancana and the CIA? East Coast mobster Meyer Lansky established Havana, Cuba as a gambling haven in the 1950s. At the time, Cuba was  run by corrupt dictator Juan Batista. In 1958, communist rebel leader Fidel Castro overthrew  Batista. Though Castro had promised the mob to let gambling continue in exchange

for their financial support in the rebellion, he reneged. Before Castro took over in Cuba,  it was a prime gambling spot. And then of course Fidel Castro comes in and it all gets taken away and nationalized. So the mob lost quite a bit there in terms of their ownership of hotel casinos in Havana. With the Cold War raging in 1961, the CIA under President John Kennedy launches a disastrous  attempt to retake Cuba using Cuban exile forces. Called the Bay of Pigs, the failed coup embarrasses the government and

especially the president. He soon lets it be known that he wants to get Castro at any cost. The CIA hatches a plot to kill the communist leader, but they need contacts within Cuba to pull it off. So the agency approaches the mob. The mob is only too happy  to oblige. They want to reestablish their lucrative Cuban gambling empire. Giancana experts acknowledge Sam’s involvement but disagree about how far it went. And I’ve often  wondered how seriously Sam Giancana even took that

because on one hand he has the FBI all over his back and then he’s got someone coming to him saying the CIA would like you to kill Fidel Castro or set up a contract. Yeah, I don’t think Sam Giancana or the New York mobsters or the Florida mobsters would have been unhappy if Castro was killed, but for them to get directly involved in this is another thing. I mean, these are people who don’t spend their lives cooperating with the United States government. I have every reason to believe that they tried. I saw

documents, I saw CIA reports, I saw individuals who testified that they tried through the mob to go after these to go after Fidel. Gangsters don’t kill heads of state. Now, Sam Giancana might have been willing to play along hoping that well, maybe if I act like I’m cooperating with the CIA, isn’t this all the same thing? CIA, FBI, what’s the difference? One hand washes the other. Maybe I’ll just act like I’m going along and you know, maybe this will get the FBI off my back partially, which it didn’t. So I

think he was just pulling their chain to some extent. Giancana certainly never felt badly about taking money from somebody to do something. That God knows the CIA would spread money around in any any way they could. Giancana allegedly takes the money and agrees to go along with the affair so far as offering contacts. Giancana also suggests to friends that getting Cuba back for the mob would give him a stronger standing in the National Syndicate. So begins one of the most bizarre chapters in the history of the CIA’s

involvement with organized crime. The CIA labs come up with a pill of botulinus toxin that can be slipped into Castro’s  drink. But before the toxin can be used, the high-level insider recruited to administer  the toxin is demoted. Then it’s arranged to have the owner of Castro’s favorite restaurant put poison in his soup. Castro stops favoring the  restaurant. The ideas become even more preposterous. The CIA creates an exploding seashell to be placed near the spot where Castro

swims. They devise a deadly fungus that can be sprayed onto the breathing apparatus of his diving equipment. Then there’s the exploding cigar and the poison cigar. What was Giancana’s reaction to this? Yeah, I’ll bet you he got a good laugh out of some of those plots. Some of it was pretty far-fetched. That’s not how organized crime families handle they when they want to take someone out, that’s not how they do it. Absurd as it is and unsuccessful, the clandestine plot to kill Castro has

serious  repercussions at the highest levels of government. Either President John Kennedy had never informed  his brother or both brothers never informed J. Edgar Hoover that a top-level government agency had been reaching out to the mob behind the FBI’s back. Hoover first learns about it from his Chicago field agents  when they’re snooping around the Armory Lounge one night and find the box of CIA surveillance devices.    The FBI chief is outraged.  The

CIA is jeopardizing the surveillance operation of the FBI’s biggest mob target. Attorney General Robert  Kennedy tells the CIA director that the agency is never to do business with organized crime without clearing it with him. Recent revelations suggest that Robert  Kennedy knew of the CIA operation but bowed to his brother’s obsession to get Castro after the failed Bay of Pigs operation. The plot to kill Castro only  comes to light in 1975 in congressional hearings.

Two people involved in the plot, ex-CIA agent Robert Maheu and gangster Johnny Roselli testify. Roselli is found dead a year later  in an oil can off the coast of Florida. Sam is also subpoenaed to testify,  but something happens before his testimony. Perhaps he knew more than anyone realized. In the spring of 1965,  federal prosecutors and the FBI decide to make an all-out attempt  to prosecute the Chicago Outfit with Sam Giancana as its most visible  and powerful target.

They don’t get very far. During the intensive investigation against Sam Giancana,  it was realized that he had too many layers between himself  and the actual crimes. And what they did was since they had no chance of gathering evidence directly to implicate Giancana, they would decided they would give him immunity from prosecution and then put him in the grand jury and ask him the questions based on all of the investigations  that had been conducted. Well, I don’t think the local FBI ever

thought that Giancana  was was ever going to tell them anything and certainly ever going to be held accountable for anything he ever did. But he was a stand-up guy in that respect. He was an old world mobster. He would not testify. They put him in jail for refusing to testify and he spent approximately a year in jail. Mr. Giancana, could you answer just a couple of questions? It’s been said so many times that your associates are more dangerous than the federal government. Sir, is that

true? How long are you willing to stay in jail, Mr. Giancana? I’ll go right now. Under what circumstances, sir, would you change your mind? Languishing in the Cook County Jail, Giancana offers  $100,000 to any lawyer who can think of a way to get him off. But the entire case is so novel that aside from a lengthy appeal to the US  Supreme Court on the entire legality of the case, there’s nothing Giancana can do but wait. During the year,  the FBI takes a lot of heat for their actions.

For all the seven years, the thousands of man-hours and the hundreds of thousands of taxpayer dollars spent on FBI  surveillance of the Chicago boss, they have no substantial evidence that Giancana  has violated any federal statutes. At the end of the year, a decision is made. I think the sentiment  of the public was, “Okay, after a year, if you got something on him, bring it out because you’re just holding him and you’re on this flimsy charge. So either do something with him or set him

free.” On June 1st, 1966, Giancana leaves the Cook County Jail a free man, but his role as the boss of bosses of the Chicago Outfit is over. When Sam Giancana finally gets out of jail, Accardo, as the chairman of the board, with Rigas’ full backing, meets with him and I think it was basically made clear to him that you can increase your life expectancy by getting out of here. That you’re out as boss. We’ve had enough of you and your annex and all the tension you bring down on us that messes

up everything. And so he decided to cut his losses and go to Mexico where he planned to set up international gambling operation. He was still a member of organized crime and it was on behalf of organized crime, but he planned to take a hefty cut. Because he was not the emissary of the Chicago mob. He was not a partner with the Chicago mob in those as seems to become clear later when he finally returned to Chicago. In exile, he manages to set up gambling ships in the Caribbean as one solid source of income.

Then on the night of July 18th, 1974, Sam’s new life falls apart when the Mexican  police sneak into his backyard. He was just puttering around in his house. He was literally grabbed and thrown out of Mexico. They literally came one night and put him on a plane in his bathroom and said you’re out of here. No one knows why Giancana is deported from Mexico.    He returns to Chicago unceremoniously wearing old clothes given to him by the Mexican authorities  

 and his bedroom slippers. He once more takes up residence at his home in Oak Park and  tries to re-establish his ties with the outfit. But organized crime is falling under  increasingly heavy scrutiny in the mid-70s. Well, part of the reason that they weren’t as powerful  the Chicago outfit and organized crime in general across the country was the efforts of law enforcement. And it would just got extremely difficult to operate. Uh they were being watched, they were

being indicted, they were being convicted. With so many mobsters going to jail and so many rackets being shut down, the mob’s power is ebbing away. So are its bank accounts. Rather than welcoming Giancana back, Tony Accardo puts the squeeze on him. I think there was some disagreements between Accardo and he about the things that Giancana had established, the gambling concessions that Giancana had established and whether or not that should belong partly or wholly to the Chicago mob as opposed to

exclusively to Sam Giancana. On top of everything else, Giancana is also being sought to testify again in Washington. And he was given a subpoena at that point for an appearance before Congress concerning his knowledge and involvement in the plot to assist the CIA in the murder of Castro which was going to be the subject of hearings.    On the evening of June 19th, 1975  about 10:30 p.m. an old friend visits Sam in his basement kitchen. Sam  cooks a snack, Italian

sausages, while they chat. With Sam’s back to his visitor  as he tends to his cooking, the man puts a .22 caliber pistol to the back of Sam’s neck and pulls  the trigger.    The killer leans over the fallen man and puts another bullet in his mouth, then sticks the gun under Sam’s chin and pulls the trigger five more times. No one is ever arrested for the crime. His death remains a mystery. Why was he killed? One argument is that he was refusing to

share in what he’d established in Latin America and elsewhere while he was gone and that Accardo had come to him and said, “This isn’t yours. This is ours.” The other one is the CIA killed him. He could really make the government look like kind of like a bunch of schmucks, really. Well, there was indications that Sam Giancana thought he should go back to be number one. And when Sam came back and started mouthing off that he was going to take over again, he signed his own death

certificate. And it was their way of retiring you. There’s no pensions in organized crime. Then comes the question, who killed him? The usual suspect in this instance is a guy named Dominic “Butch” is his nickname Blasi who was for years Giancana’s closest confidant. He’s known to have been there that night because his car was there and the police saw him leave. The gun that actually killed Sam Giancana, a .22 with a silencer, was found in River Forest next to Oak Park which would have been

along the route that Butch Blasi probably would have taken home after leaving Giancana’s house. Sam Giancana is buried in Mount Carmel Cemetery  on June 22nd, 1975 near the graves of his wife, mother, father and sister. None of his old gang shows up. Not the mobsters who had shared in his heyday, not his mentor Tony  Accardo, not his celebrity pals like Frank Sinatra or others in the Rat Pack. Only his immediate family attend  and former girlfriend Phyllis McGuire. Why does Sam Giancana continue to

fascinate  people more than two decades after his violent death? Basically, I think it’s  an outgrowth of the fact he’s rubbing shoulders with the famous that he did know a lot of famous people and he was indirectly connected to some of them like the Kennedys by sharing    a mistress Judith Campbell with John F. Kennedy, that he knew the Rat Pack in Hollywood. He was in the public eye and therefore,  given the number of interesting events that occurred during

that period including  elections, assassinations, suicides, things of that nature. And the American fascination  with the mob. My theory was always that Giancana wanted everybody to believe that he did all these things, that he got John F. Kennedy elected, that he got John F. Kennedy killed, that he killed Marilyn Monroe, that he dated Marilyn Monroe. I think he loved all of the speculation, that he was all powerful and could do all of these things. I think he basked in that. Sam Giancana’s ruthlessness,

his violent  temper, the fear he instilled gave him the power to enforce discipline and create an organization whose power allegedly reached to the very doors of the White House. His enormous ego, his  attitude of invincibility, his love for publicity led to his downfall. Sam Giancana attained  his dream. He became the most powerful crime boss in America in the 50s  and 60s. Never has an underworld figure had so much influence in labor, in  politics, in foreign affairs, as well as

criminal activities. He earned the right to be called  the boss of bosses and paid the price.