Uncovering The Deadliest Mob Boss In History | Mafia's Greatest Hits | @RealCrime

[Music] [Applause] [Music] [Music] Sam janana was the most flamboyant gangster of them all when organized crime was at its most extravagant I say he was far more powerful than El Capone and he was a giant he had a beautiful chiz girlfriend he was Pals with Frank Sinatra Sam Jan car didn't like to keep a low profile he liked the big life he liked to be seen with the Stars he was worth millions and had the power of life or death he killed a lot of people he had a lot of people killed one cold stare from you and could cause you to become very concerned if you crossed them you were in deep trouble but in helping elect a clean young president and assisting in the cia's murkiest operations his career sees the mafia and politics mix into a deadly cocktail the pursuit of Sam janana is the ultimate story of the State versus the mob and the final chapter is one of the most notorious Mafia hits of [Music] [Music] all Sam janana had learned his gangster trade from Al Capone's top enforcers he excelled as a driver delivering Killers to murder their victims and evade the [Music] cops he learned how to lend money and collect the interest hey Sam loan me a five I got to go get something he said um what do it take for security and Sam said how about ali his Furious outbursts were so Savage that people around him wondered about his mental stability he was violent but the people in the Chicago outfit almost are all violent they kill people with the drop of a hat he was a killer aged just 18 janana was charged with murder but escaped conviction when I first saw Sam J con I thought there is the arrogance the hatred the violence the viciousness that I've dedicated my career to [Music] fighting for the mob Jana's greatest strength was not his violent nature but his gift for making money it was janana who struck fear into the electrician Union so that every slot machine in Chicago paid the mob it was janana who mused the black gambling Kings out of Chicago with threats and murder under his watchful eye millions of dollars poured in from casinos in Las Vegas in Cuba and by 1957 aged 49 Sam Muni janana was boss of the Chicago outfit Sam Gian Conor was the most powerful criminal Chief in the history of the United States he had his tentacles into the police to the courts to the business world around Chicago but just as Jen Conor reached the top the government turned on organized crime an eager young lawyer began fighting to see him and his kind fall Robert [Music] Kennedy the nation's underworld gets the unwelcome Spotlight of publicity as the Senate's investigation subcommittee begins new hearings on crime Arkansas Senator M the Senate labor rackets committee was investigating Mafia Corruption of the trade unions Robert Kennedy Chief legal counsil made a name for himself by questioning witness after witness about their mob connections did you say at SOB I'll break his back who did you make it about I don't know I may have been discussing somebody in a figure of speech well who did you make the statement whose back even remember it well whose back were you going to break Mr hoer take give your speech I don't even know who I was talking about I don't know what you're talking about I mean it was real life drama and uh and it was exciting to watch on the 9th of June 1959 the witness was Sam janana you tell us uh whether if you have opposition from anybody that you dispose of them by having them stuffed in a trunk is that what you do Mr Jean Conor uh would you tell us Jena refused to answer Kennedy's questions by taking what is known in America as the Fifth Amendment when you take the fifth you say essentially I respectfully decline L to answer on the grounds that my answer might tend to incriminate me and nobody can touch you for it Sam janana asserted his Fifth Amendment rights over 30 times declin answer because I H believe my answer might turn incriminate me Chief counsel Robert Kennedy seemed frustrated and goed the gangster will you tell us anything about any of your operations or just I giggle every time I ask you a question declin to answer because I honest believe my answer might tend to incriminate me I thought only little girls giggled Mr Jan Bobby Kennedy's theatrics were perhaps intended to light Jen's famously short fuse I think he was hoping that yukana would explode but you know I never thought he really gave a [Music] damn round one in this long bit of Feud went to Sam janana Kennedy could get nothing on him [Music] and there was a reason why the Chicago boss felt Untouchable he was well connected to the [Music] kennedies Robert Kennedy's Big Brother Senator John F Kennedy had set his sights on the White House but just to become the Democrat presidential candidate was a battle a Boston Irish Catholic couldn't get elected to anything in staunchly Protestant states of 60s America like Wisconsin and West [Music] Virginia the wealthy Kennedy Clan would have to buy support in these key primary elections so they reached out to an influential family friend for help Frank sinata Sinatra was a friend of the the Kennedy family the family and Jack Kennedy in in particular Frank in his turn had a friend and business partner who knew all about getting his way in politics Sam janana I have every reason to believe that there was mob money in in the West Virginia election the person who handled the money was Frank Sinatra before voters went to the polls janana sent one of his men to spread $50,000 around West Virginia he sweetened local politicians with new office fiture and paid bar owners to keep Sinatra's campaign song High Hopes playing on Juke boxes across the [Music] state Jana's efforts seemed to help get the kennedies over the first hurdle John F Kennedy became the Democrat candidate to run for [Music] president but an even bigger challenge lay [Applause] ahead in November 1960 John Kennedy faced the sitting vice president Richard Nixon in the race for the White House the election was too close to all pundits were saying that whoever won the state of Illinois would win the presidency and the key to Illinois was Sam Jen's backyard Chicago janana Chicago outfit knew all about how to swing votes in their City they've been doing it for Generations in this city no criminal Enterprise is going to work until they've got the politicians in their pocket he had the politicians and I mean all of them one Rus was to send scores of people from Precinct to Precinct illegally voting in each one another well-worn trick was Ghost voting impersonating deceased residence of a [Music] Precinct bobc controlled unions were prevailed upon to vote Kennedy to a man there were even claims that Jan's hoods intimidated voters at the polling [Music] stations listening to the radio listening to the returns coming in it was obvious that there was a theft [Music] underway not since 1916 had the presidential election result been so close Kennedy beat Nixon by just one tenth of 1% somewhat afternoon on the day after the election Senator Kennedy received a telegram from the vice president congratulating him on his victory with this in his Sam janana was quick to claim that it was he who had elected Kennedy to the White House While most dispute this janana certainly expected Payback Gian kaana can legitimately think that he had done his work and that he had tipped it and that he could expect some result janana expected the new Kennedy Administration to get Bobby off his back he told an associate Bobby will just be another goddamn lawyer soon they promis me they'll take care him I am in my mind and convinced that there was a deal cut that uh if Gian Cara would get Illinois for the Democrats that he would be given free hand janana prophesied to the outfit a lessening of government harassment in Chicago and Las Vegas he couldn't have been more [Music] mistaken new president President John F Kennedy appointed his brother Bobby to the government post of Attorney General I have felt that we should secure the best talent we could get for every position regardless of uh party regardless of any other Factor this test has been applied it's been implied in this case far from being just another lawyer as attorney general the fanatical mob chasing Robert Kennedy was now the country's top law enforc ment officer it was a shock for janana and the Chicago outfit the last thing they thought was they would get Robert Kennedy as the Attorney General anybody but Robert Kennedy that was a surprise Bobby Kennedy now in charge of the Department of Justice and the FBI declared war on the mafia I think that in the field of organized crime I think it's an a very serious situation that's facing the country at the present time I think a lot of steps can be taken in order to deal with the problem I think it's gotten much more serious over the period of the last 10 years janana cursed at the sight of the Attorney General and fumed at the very mention of the Kennedy name to him Bobby Kennedy's war on organized crime was a betrayal but as the justice department went to war Sam janana fell in love Phyllis Maguire was the lead singer of the headlining Trio the Maguire sisters she was 29 janana was 52 it seems violent Mo janana could be charming and he wasn't flashy it was just direct and it was uh strength and uh his eyes were it's like they looked through you she was a big star stunningly beautiful and he loved to be seen out with her on his [Music] arm janana began to flood her with gifts of Furs cars and jewelry cash had always bought him the most beautiful escorts but this was different he began to neglect business in Chicago to follow Phyllis performances all over the US he even accompanied her on a two-e European tour the tough mob boss had a [ __ ] in his armor a weak spot the government would later use to help bring him [Music] down while janana was Romancing Phyllis attorney general Bobby Kennedy was hard at work radically reforming the Department of Justice and the FBI he was extremely driven he absolutely hated what he called the outfit the mafia organized crime to the 10 FBI agents assigned to Chicago Kennedy added 60 more janana called them gmen or just the G at first he was unconcerned dismissing them as Boy Scouts up to now their track record against organized crime had not been good but Kennedy was changing the game the FBI agents that descended on janana were a new breed they were all cleancut college educated men many were lawyers above all the biggest problem for Sam Jan Carana was that these government men had a fanatical commitment to their incorruptibility unlike other Chicago Law Enforcement janana couldn't buy them Robert Kennedy was also increasing the number of lawyers in the Justice Department's organized crime and racketeering section from 17 to 63 he rebuilt the whole operation you can think of the Department of Justice as a a aircraft carrier and you can't turn an aircraft carrier on a dime they don't have brakes you can slow it down and steer it he turned it on a dime and took it in a different direction the Attorney General funded his new crack team of investigators well his goal was to get all government agencies working together as never before to break the G of organized crime he talked directly to you it gave us a whole feeling of electricity and what we were doing and commitment to what we were doing we did feel that we were kind of like the new [Music] Untouchable jenana was now closely watched by the New FBI agents in Chicago the view is fine and the kids are still in school over his HQ was in the back of the Armory Lounge Bar and Restaurant in Chicago's Forest Park suburb despite FBI surveillance his private business remains secret behind closed doors eyeball one to Dugout I read you loud and clear or so he thought 10 three eyeball one stay with [Music] him the Gman had a new weapon that would turn Jan's world upside down electronic surveillance Bobby Kennedy decided that organized crime was an issue of National Security it was a threat to the United States and fell in that category that you could exercise a wire tap and install a w tap without a warrant the number of FBI bugs and wir TAPS in America exploded from just a handful to hundreds the FBI agents Roma and Hill assigned to monitor janana were quick to hide a microphone in the holy of holies his HQ the Armory Lounge the gmen overheard poy po an old associate complaining about them to Mooney janana I never thought it would be this [ __ ] rough you told me when they put his brother in there we're going to see some fireworks but I never knew it would be like this this is murderate on certain individual you mean the outfit yeah the agents had exactly how janana ran the outfit although officially the boss he received advice from senior mob figures and retired boss Tony a cardo L Mo oh we aren't here to try twist your mind we're just giving you what's practical practical advice that's all we're not here to try to distort you the tapes also revealed how janana advised his driver and bodyguard but blasi about the mafia Code of Silence omera he warned about the penalties for blabbing mob business to Outsiders there was a a fish Over the Bar and he points up to the stuff fish and says you know how that fish got that way he opened his mouth and of course he's saying this into a bug himself but he's telling um but blousy to uh to don't talk about all that kind of stuff FBI agents Roma and Hill in their surveillance of Jan Carana did their utmost to exploit his weak spot the relationship with Phyllis Maguire they watched Sam and Phyllis closely very closely they took photos and shot moving footage of them together when they went [Music] out with wire Taps and bugs they also listened when they stayed in even recording their conversation in their bedrooms whether in Las Vegas or Maryland Pittsburgh or Atlantic [Music] [Applause] [Music] City the pressure of tight surveillance got to Sam janana his acid anger was fired at the Gman whenever he saw them AR Roma he spots it he says hell Mo and he walks away then we move out of there into the other room and who the [ __ ] walks in but that [ __ ] [Music] Hill janana started to lose control he antagonized the agents and hissed obscenities retired boss Accardo was concerned that janana would do something stupid stupid don't call them dirty words or anything don't pay attention just walk away from them let them talk you guys I would go [ __ ] yourselves and this and that Bast they're just like us they got a job to do we know what to do and we do it I [Music] know Bobby Kennedy was tightening the news but one government agency had jeopardized all his work by secretly seeking Jan's help the CIA the consequences for the agency and for janana would eventually be dire janana and many other gangsters had once ADV vased lucrative business interests on the island of Cuba just a short hop from Miami in exotic and poverty-stricken Cuba white tourists with green dollars could live like royalty and lose money in the compet of the mob owned casino hotels Cuba was a gold mine for the mob it's a lot of money made down there in the casinos and the joints and Castro took it away completely on New Year's Day 1959 Fidel Castro's Rebel forces swept into Havana and with popular support supplanted the old mob friendly regime of President Batista Castro swiftly nationalized land and American businesses he cost the mob and the US government Untold millions of dollars the mob they were running this Cuba they were running a muck down there under Batista and when Castro came in he threw them all out so they were not happy with him if they could get rid of Castro they could move back in it wasn't just the mob who wanted Castro gone the CIA saw Castro as a dangerous communist on America's doorstep and they wanted him swept away so who would you go to you go to mob guys who had good Connections in Cuba they operated there for years and are pretty good at killing people on the basis that my enemy's enemy is my friend the CIA met janana and Associates to try to arrange a Gangland hit on Cuba's president Fidel Castro they're certainly naive about the organized crime they're not a hit squad you can't buy them to kill people they thought they could at a clandestine meeting at the font and blur Hotel in Miami the CIA wanted a Capone style attack with Castro going down in public in a hail of [Music] bullets the real life gangsters demurred wanting to keep things nice and clean janana suggested something much more CIA using pills to poison Castro's food and drink the CIA took his advice but when a US government agency secretly commissioned murder from gangsters they should have seen trouble coming and once you've dealt with them and they've given you something then they have a right to ask for something back and you don't want a reciprocal relationship with them you're compromised master manipulator janana soon turned the situation to his Advantage first he's working for the CIA and then somehow they find themselves working for [Music] him Jan Carana suspected Phyllis Maguire of having an affair in Las Vegas with top shis comedian Dan [Music] Rowan he talked his CIA contact into arranging to plant a microphone in Rowan's hotel [Music] room but the the operation went terribly wrong the installation Engineers were discovered by Hotel staff and arrested by police the CIA feared the mob connection and Castro assassination plot would get out the agency did not want that plotting to come public and they were afraid to death of any public examination of gan carna to avoid a public trial a deeply embarrassed CIA director of security Sheffield Edwards had to confess in a memo to the FBI the whole sorted Affair when he found out the Attorney General Bobby Kennedy was Furious and he called sheffel Edwards in to his offices and what he said was the next time you do something like that you talk to me first one day all this would come back to haunt both the CIA and Sam janana FBI agents Roma and Rutland watching and being verbally abused by janana in Chicago now put even more pressure on The Bard outfit boss toer determined to drive him over the edge the agents implemented what they called lockstep surveillance every day Round the Clock they were with him following in cars when he got out they got out when he walked they walked within feet of him they followed him on his golf round rushing his game jeering from the edge of the greens they were like this he played golf they were behind him just everywhere he went and it sent him off like a Roman tand they even followed him into restaurants if he went to the restroom an agent would also go and stand at the next urinal which made it difficult for him to do what he had gone there to do it was pure simple harassment they weren't getting anything out of that real and Rutland would right about one thing it drove janana mad an electronic surveillance recording made in June 1963 reveals that his mob Associates thought he was becoming dangerously irrational that [ __ ] Jun wait till you hear what he's done now he's now making good decisions what happened Charlie McCarthy told Roma that Mo told him to tell Kennedy to talk to him through Sinatra for Christ's sake that's a God in no rule we don't give up a legit guy he tells Roma that sinak is our guide of Kennedy more or less I'm so [ __ ] mad I could jump out your window I we got to do something about the G is driving this man [Music] goofy a Madden janana lashed out in a way the mob would never understand he sued the FBI saying their lockstep operation violated his civil rights Jan's lawyer hired a film crew to shoot the FBI lock Step In Action in a darkened courtroom the judge was also shown Jan's respectable lifestyle playing a round of golf going to church and visiting his father father's grave an injunction against lockstep surveillance was granted the FBI agents would have to keep their distance Sam janana had for the moment beaten the FBI but Jan's Victory soon evaporated and to escape the continual scrutiny he and phis holiday that Sinatra's home in Palm Beach and then in Las [Music] Vegas meanwhile the FBI was recording some disturbing mobster conversations with Kennedy a guy should take a knif and stab and kill that [ __ ] I mean it this is true Hest the God right in the White House some got to get R of that [ __ ] the Kennedy's war against organized crime was fueling a dark mood among gangsters all over the United States they should killed the whole family the mother and father too just a few months later on November the 22nd 1963 President John F Kennedy was assassinated during a Dallas motorcade [Music] [Applause] The Killing spawned a rash of conspiracy theories about who might be responsible there was always a strong rumor that the mob had something to do with the assassination of of John [Music] Kennedy the rumors of Mafia involvement were fed when it was revealed that the man who gunned down Kennedy's assassin Lee Harvey osw world was mob fixer Jack [Music] Ruby it didn't go unnoticed that Sam jenana had sought Ruby's help from time to time but despite the rumors there has never been anything to substantiate claims that the mob had any part in it President Kennedy's death did however give the mob what it wanted the immobilization of his gang busting brother I think he was simply crushed and shocked by it an FBI informant heard Jan's reaction what he said was chilling Attorney General Robert Kennedy will not have the power that he did Within year the new president appointed a different attorney general and Robert Kennedy was gone janana thought the pressure was off but Bobby Kennedy had rebuilt the justice department to smash organized crime even without him the Machinery worked on crucially Kennedy had inspired a generation of investigative lawyers who would not give up the fight one of Bobby's boys was a young lawyer in the Department of Justice Strike Force David shippers always there was a Sam Jan con hanging out there the one guy that nobody seemed to be able to touch all he had to do was surface once and we'd be able to put him into a conspiracy of some kind couldn't find [Music] anything Chipper's problem was a lack of Hard Evidence the FBI agent years of electronic surveillance put janana at the center of extortion illegal gambling and murder but as the bugs were installed under presidential prerogative and not by a Judicial warrant the thousands of hours of incriminating recordings were not admissible as evidence in court but determined to put janana behind bars shippers meticulously constructed a cunning legal snare first to question janana about his criminal career shippers awoke the dormant power of an investigative grand jury without the grand jury we were dead in the water we couldn't do a thing because we had no personal subpoena power it was a grand jury that had the subpoena power if you were subpoena to the grand jury you got no choice you got to show up you may take the the Fifth Amendment but you're going to you're going to get dragged in there second shippers had to stop janana hiding behind the fifth amendment by removing any possibility that he could incriminate himself if what you're saying can never be used against you then the Fifth Amendment doesn't apply that's where the use of immunity came in granting immunity from prosecution to a top mafia boss was a bold step and A Hard Sell to shipper's boss the US attorney the US attorney looked at me and he said are you nuts are you crazy they said what you don't really think he would talk we wouldn't immunize him if we didn't think he'd talk if he doesn't talk we'll put him in jail if he does talk we're going to have one heck of a great case will'll break the whole stupid Mafia at last the Trap was set but wouldi andana take the bait in December 1964 the Federal grand jury investigation began to soften janana up shipper summoned his mob Associates to question them in secret janana feared they might be spilling their guts but he couldn't be [Music] sure then to play even more on Jan's increasing paranoia shipers exploited his weak spot he seped Phyllis Maguire [Music] so here comes Phyllis Maguire we're going to put her in the grand jury I just assumed she's going to come in and answer our questions and the questions were essentially would essentially have been about her Association nothing embarrassing she was the key to this whole thing Phyllis seemed shaken by The Experience whether she actually testified or asserted her Fifth Amendment rights and declined to answer is still secret but the thought that Phyllis had told them anything sent the paranoid janana crazy you know he said over the weekend that he was pretty angry with have you talk to him about it no comment well the word came back to us that Sam chanana was ready to kill himself is this an indication do you think that your relationship is all over no comment because he thought if she talked I'm in trouble David shippers scheduled janana straight after Phyllis and made sure he reinforced Sam's fears when they met just before questioning I had a a transcript of another individual's testimony in some case was about a/ inch thick and we had the uh court reporter put a page on top that said testimony of philis Maguire and I know Sam saw it shippers had janana right where he wanted him on the witness stand the Chicago boss thought he knew the rules of this game he'd plead the Fifth Amendment to each question question and go home as usual but he didn't realize David shippers had changed the rules I remember the judge saying to him Mr Gan kanana if you received a traffic ticket on the way in here today nobody can touch you you are immune from any prosecution for any crime as of this moment immunity effectively stripped janana of fifth amendment protection and then it really hit him when the judge told him he was immune and he had a talk He was ordered to testify then it hit him the single-minded purpose of David shippers seemed to remind janana of an old adversary he turned to me and he said you're one of Bobby's boys aren't you I said yes sir I am janana had no choice if he talked and lied he was certain to purger himself if he talked and told told the truth the mob would kill [Music] him janana gave his name and address invoked the fifth and the trap was sprung Sam janana boss of the Chicago outfit by refusing to answer questions was in contempt of court and taken straight to jail Sam ganana was totally OD he was rattled he couldn't understand how this could happen the judge commented that janana had the key to his own cell he would be released when he decided to answer the grand jury's questions but in the outfit you don't talk janana kept his mouth shut this was a government victory of sorts as it was the first time he'd been in prison for over 20 years that rocked the whole organized crime around the [Music] country but was it such a great Victory janana could could only be held in jail until the grand jury folded a year later on the night janana was released in May 1966 there was a party at his home in Oak Park but senium Mobsters found nothing to celebrate the outfit Old Guard decided Mo Jan's high-profile and volatile temper was bad for business they gave the FBI a belated victory by stripping Sam janana of his ranker boss and throwing him out of Chicago for [Music] good janana left the us to live in quaka Mexico over the years he built a new life for himself no gmen dogged his steps or monitored his phone calls and janana returned to what he did best making money in the mid-60s as NASA prepared to put a man on the moon janana was launching a gambling operation on cruise ships in the Caribbean while the us tore itself apart over the Vietnam War Jan's International Ambitions met with success in Guatemala and with the sh of Iran in 1968 his old adversary Robert Kennedy ran for president but on the campaign Trail he was gunned down and killed and although the 70s saw an aging janana undergo abdominal surgery he enjoyed a quiet wealthy life then suddenly a dark episode from his Past cast a chill Shadow over Sam Jano his connection to the CIA in January 1975 a senate select committee began investigating illegal CIA operations specifically CIA involvement in plans to assassinate Castro its findings would shock chairman Senator Church it is simply intolerable that any agency of the government of the United States May engage in uh murder the committee was very interested in hearing from any Mobsters consulted by the CIA in their Castro assassination plots although lying low in Mexico janana had been snatched from his Hideway and suddenly found himself deported back into the United States the Press were waiting why did you have to leave Mexico sir why I don't know Mr J what are your future plans the future plans of onetime Boss janana were to reestablish his cut of Chicago outfit operations once he arrived in Chicago he announced to the to the ENT organization that he was back and he was the man but a new generation ran the Chicago outfit they had no room for the Aging janana by that time a lot of his Rivals were in the penitentiary or dead because of what we been doing to them knocked out of action in Chicago janana received a subpoena that ordered him to appear before the senate committee without fail in Washington DC on June the 24th 1975 but Sam janana never made [Music] it on June the 19th 1975 4 days after celebrating his 67th birthday Sam janana was at home in Oak Park Chicago he was cooking in his basement kitchen routine police patrols noticed nothing [Music] unusual health problems meant he could not eat spicy foods so it seems the sausage and peppers was a late night snack for a [Music] friend a friend janana liked and trusted a close friend but the mafia hadn't quite finished with Sam [Music] [Applause] [Music] janana the way he was killed showed that the mob no longer trusted him to keep quiet he was shot in the mouth so that you might draw the conclusion that somebody was leaving a message don't talk it was somewhat interesting that that somebody that powerful uh was was killed so there had to be a major major decision among uh the uh the the powers to be in the M Sam Jan's extraordinary career had lasted over 50 years spanning the Heyday of organized crime in America in the years after janana show business Stars began to shun any mob connection the Glamorous image of gangsters became tarnished people realized they were just Killers never again would a Mafia Boss be so closely associated with the bright stars of show business or the dark underbelly of politics the FBI and the justice department had struck the first serious blows aimed at breaking the [Music] [Music] mafia [Music]

Channel: Real Crime

Views: 792,671

Keywords: FBI informants, FBI investigations, Real Crime, crime biographies, crime boss stories, crime documentary series, crime families, crime history, crime scene investigations, criminal activities, criminal informants, criminal justice system, dark underworld secrets, gangland killings, gangland wars, hitman stories, mafia families, ruthless mobsters, secret societies, sinister underworld, violent crimes

Id: u9ZD9nWpYpg

Length: 49min 38sec (2978 seconds)

Published: Sun Apr 07 2024