Frank Sinatra Pt 2: New Evidence, Secret Favors, and Three Dead Men. This is Frank Sinatra — Connected, Compromised, and Cornered

Summary

DISGRACELAND: Frank Sinatra Pt 2 — New Evidence, Secret Favors, and Three Dead Men
Episode Date: July 1, 2025
Host: Jake Brennan

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Episode Overview

This gripping episode of DISGRACELAND explores Frank Sinatra’s deep, transactional, and deadly connections with the Mafia. Using new research and unreleased law enforcement files, host Jake Brennan dives beyond Sinatra’s popular image to reveal how “The Voice” wasn’t just mob-adjacent but often neck-deep in criminal enterprise. The episode climaxes with the infamous kidnapping of Sinatra's son—an event that triggered Mafia violence and FBI intervention, leaving three men dead in the shadows.

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Key Discussion Points & Insights

The Mafia Hierarchy and Sinatra’s Unofficial Role

• Brennan introduces listeners to Mafia structure: bosses, captains, soldiers, and “connected guys," underscoring the gravity of being “made” in the organization.
  • [03:03] “This is a story about the Mafia and about one musician's position in the Mafia. This is not a story you've likely heard before...not just a story about a singer who needed the Mob's help. It's about a pop star who was expected to deliver for the Mob over and over again...”
• Sinatra was not a made man but was more than a mere associate. He was, in Brennan’s words:
  • [08:16] “Frank Sinatra wasn’t just a wannabe. Frank Sinatra...was himself very much a gangster.”

Early Mafia Patronage & Violence Clearing Sinatra’s Path

• The Mafia financed Sinatra’s career: buying suits, funding headshots, and leveraging violence to free him from harmful contracts.
• Key story: In 1942, mob enforcer Willie Moretti threatens Tommy Dorsey to break Sinatra’s exploitative contract, paralleling the infamous “Godfather” horse-head scene.
  • [22:32] “William Moretti put a gun to Dorsey's head... ‘either your brains or your signature's gonna be on that contract.’ Dorsey, of course, signed, releasing Frank Sinatra from his contract.”
• Sinatra “earned” for the Mob by performing at their clubs and—later—helping them acquire and profit from nightclubs and casinos.

The Sinister Side of Celebrity: Havana and Las Vegas

• Havana, 1946: Sinatra acts as a literal bagman, carrying cash and a gun to the Mafia’s Havana conference, followed by a deadly altercation in his hotel suite.
  • [15:36] “Frank’s gangster buddy sent Alora Gooding home quietly to the States, while Mafia controlled Cuban soldiers cleaned up the mess. Frank Sinatra went about his business...secure in the fact that the Mafia wasn’t going to let anything as insignificant as a couple of dead Cubans submarine their investment...”
• Las Vegas and Cal-Neva (1950s–1960s): Sinatra’s financial stakes in mob-run casinos—despite IRS debt—demonstrate his privileged, protected status.
  • [31:24] “Frank Sinatra was allowed… to invest in the Sands Hotel and Casino and retain a 7.5% ownership piece. Mob boss Frank Costello was the majority owner…Sinatra was thus earning for the mob big time.”

Sinatra, the Kennedys, and Electoral Fraud

• Sinatra becomes the intermediary between the Mafia and the Kennedys in 1960, helping swing elections, notably in West Virginia and Illinois, for JFK.
• Scene-setting at the Cal-Neva: a star-studded, mob-packed party involving Sinatra, Sam Giancana, Joseph Kennedy, JFK, and Marilyn Monroe, all observed by federal surveillance.
  • [33:24] “This was not a secret. The gangsters, the corrupt former ambassador, the adulterous and brazen senator, the glamorous movie star mistress, with Frank Sinatra at the center of it all and the FBI listening and snapping pics.”
• The relationship sours as RFK targets the Mafia, forcing Sinatra out of Kennedy’s inner circle and triggering deep mob resentment.

Downfall: Humiliation, Betrayal, Assassination, and Kidnapping

• Sinatra’s failed attempt to keep his influence—preparing his Palm Springs estate for JFK, only to be coldly shut out—marks the turning point.
  • [37:34] “Frank spared no expense. And then Frank got ghosted by the President at the last minute...The humiliation. Frank Sinatra was out and Sam Giancana was pissed. Frank had no juice.”
• The episode highlights the conspiracy theory that the mob may have been involved in JFK’s assassination, with Giancana and Sinatra left empty-handed by the Kennedys.
• Just as Sinatra fears retribution from the Mafia, his son Frank Sinatra Jr. is kidnapped—a crisis both existential and criminal.

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Most Notable Stories & Memorable Moments

The Havana Incident — Fatal Chaos

• Vivid, pulp-style retelling: Sinatra’s girlfriend shoots a guard at the Hotel Nacional, and the Mafia cleans up; Sinatra strolls away unscathed.
  • [15:36] “Frank’s gangster buddy sent Alora Gooding home quietly... Frank Sinatra went about his business that weekend...secure in the fact that the Mafia wasn't going to let anything as insignificant as a couple of dead Cubans submarine their investment...”

The Cal-Neva and Power at the State Line

• Mob bosses who couldn't legally enter Nevada manipulated property geography to stay involved, while Sinatra operated at the center of the action.

The Kidnapping of Frank Sinatra Jr.

• Sinatra’s gut reaction is to call mob boss Sam Giancana before the police or FBI, reflecting the depth of his underworld ties.
  • [40:42] “Frank picked up the phone, and before he called his wife, before he called the cops or the FBI, he dialed the number of the one man he believed could help...Mob boss Sam Giancana.”
• Graphic details of the mob’s attempts to extract information—a cascade of violence, torture, and murder targeting suspects, with Mad Sam DeStefano leading the carnage.
  • [43:52] “Mad Sam had his own portable prod...the prod hit the Cowboy's testicles...and still the near dead motherfucker gave up nothing.”
• Sinatra ultimately turns to the Kennedys—his former political allies turned enemies—when mob aid fails, and receives personal assurance from RFK via Peter Lawford and Patricia Kennedy.
  • [45:22] “Bobby...pledged to use his power to help Frank get his son back...‘everything is being done and we'll get his boy back as soon as possible.’”
• Justice for the actual perpetrators is swift (and, comically, light), while three unrelated men pay with their lives—silently dispatched by the Mafia in a show of protection.
  • [50:37] “But three other men who had absolutely nothing to do with the kidnapping were tortured and killed by Sam Momo Giancana on behalf of his friend, Frank the Voice Sinatra.”

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Notable Quotes

• “Frank Sinatra wasn’t just a wannabe. Frank Sinatra...was himself very much a gangster.” — Jake Brennan, [08:16]
• “Frank couldn’t not get what he wanted… He was Frank the Voice Sinatra.” — Jake Brennan, [09:36]
• “Frank Sinatra did something that a lot of gangsters do when they’re cornered...He went to the feds for help.” — Jake Brennan, [50:13]
• “Amongst the Italians. He was helping out a friend, helping out a fellow gangster, which was without a doubt, a disgrace.” — Jake Brennan, [51:17]

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Important Timestamps

• 03:03 — Introduction to Sinatra’s Mafia entanglement
• 08:16 — The “wannabe” myth debunked: Sinatra as real gangster
• 15:36 — The deadly Havana hotel scene
• 22:32 — Tommy Dorsey contract story
• 31:24 — Sinatra’s role in Las Vegas and the Cal-Neva casino
• 33:24 — The mob, the Kennedys, and Marilyn Monroe at Cal-Neva
• 37:34 — Sinatra’s political humiliation; JFK betrayal
• 40:42 — Sinatra Jr.’s kidnapping—first call to the mob
• 43:52 — Mob torture and violence in the search for Sinatra Jr.
• 45:22 — Sinatra turns to the Kennedys and FBI
• 50:13 — Mob justice and the aftermath

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Tone & Style

Jake Brennan’s narration is stylized, vivid, and dramatized, blending pulp energy with rigorous historical detail. The tone is reverential towards music, unsparing with the underworld, and laced with dark humor. Episodes stray purposefully from sanitized biopic narratives, instead providing gritty, raw, and cinematic storytelling.

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Summary Takeaway

Frank Sinatra’s life was not merely colored by mob rumors; it was violently and fundamentally shaped by organized crime. Brennan weaves new evidence into the legendary saga, painting Sinatra as both a beneficiary and a participant in Mafia dealings—respected, feared, and, when the chips were down, as blood-stained by association as any hoodlum on the street. If you think you know Sinatra, this is the rest of the story.

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Question of the Week
Is Frank Sinatra the most gangster musician of all time? If not, who is? (Leave your answer for afterparty bonus episodes.)

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For credits and ad-free access, visit disgracelandpod.com

Transcript

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o.com that's o d o o.com Disgraceland is a production of Double Elvis. This is about the Voice, the Weasel, about the Boot and guys named Lucky Momo and Handsome Johnny. This is a story about the Mafia and about one musician's position in the Mafia. This is not a story you've likely heard before. This is not just a story about a singer who needed the Mob's help. It's about a pop star who was expected to deliver for the Mob a over and over again and in a way that only made Mafia members were expected to deliver. This story is based on recent research from a newish book that pulls from a trove of previously unreleased secret files from Los Angeles police intelligence and FBI documents. This is a story, of course, about Frank Sinatra, a story that puts him not just up close and personal with the Mafia, but but in the Mafia, running illegal errands, entering into illegal businesses, and relying on illegal favors, one of which resulted in not one, but three murders. And this being a story about Frank the Voice Sinatra means that it's also a story about great music. Unlike that music I played for you at the top of the show, that wasn't great music. That was a preset loop for my melotron called Cowboy gonna bleed MK1. I played you that loop because I can't afford the rights to Dominique by the Singing Nun. And why would I play you that specific slice of convent cheese could I afford it? Because that was the number one song in America on December 8, 1963, and that was the day Frank Sinatra's son was kidnapped and a phone call was made that resulted in the torture and death of three men at the hands of a Mafia enforcer. On this episode, new research, secret files, illegal favors, torture, murder, and Frank Sinatra. I'm Jake Brennan, and this is disgrace. Once upon a time, back during the earlier part of the 20th century. Just after Prohibition and throughout the 1940s and 50s, the American mafia consolidated its immense power. And your Mafia bosses, your Lucky Lucianos, your Vito Genovese types, created empires. These gangsters, the bosses, picture Don Corleone from the Godfather. They gave orders and stayed above the fray. Below them, there were the captains, the guys who ran the crews. Guys like Ruggerio, Richie the Boot, Boiardo from New Jersey, who wasn't afraid to get his hands dirty. He was said to bury his enemies in his backyard. And then there was Angelo Gyp De Carlo, who ran the Jersey labor unions and controlled the nightclub business and who was also known to make enemies disappear. These were more your Tessio, your fat Clemenza types. Below these guys, you had your soldiers, men like Willie Moretti, a New Jersey member of the Genovese family. Moretti once invited a man who owed him money to dinner to work out his debt. The deadbeat, of course, didn't have the money, and Moretti shot the man in the leg in front of a restaurant full of witnesses and then finished his meal as if nothing had happened. Moretti himself was shot in the face in 1951, ironically, in a Jersey restaurant while eating a bowl of spaghetti. If you want a comparable character from the Godfather for Willie Moretti to continue our analogy, look no further than Vito's muscle, Luca Brasi, or better yet, Michael's bodyguard, Al Neri. These mafiosi were so called made members of the Italian Mafia in America, which meant they took blood oaths, swearing allegiance to their mob families, swearing to live by the code of omerta, or silence. Made members of the Mafia are protected as long as they play by the rules. Their bosses and their families are there for them to keep other gangsters out of their territories, to bail them out of jail, to provide for their families when they get sent to jail, and, generally speaking, to help made men sort out whatever problems they might encounter so that they can continue to earn money for their families and for themselves. Being made was and still is one of the highest honors a gangster can receive in the Mafia. And only Italians can be made. But being made doesn't make you a boss or even a captain. Mixed in among the made soldiers were gangsters who never became made men, but who were nevertheless indispensable to their crime families. Men like Frank Cheech Livorcy from the Genovese family, who ran New Jersey's gambling and numbers operation, and Ben Bugsy Siegel, who wasn't even Italian and who literally built Las Vegas for the American Mafia. The Godfathers unmade. Men of influence are of course, Tom Hagen and Mo Green. Lots of mafiosi are not made men. They're simply connected guys. But that doesn't mean they're not gangsters. They are. And their fortunes rise and fall with the fortunes of their families. And, and this is the point, not only their fortunes, but their lives depend on their own ability to earn earn money for their bosses. With that, gangsters win and lose at life accordingly. Nobody likes a loser. Frank Sinatra especially did not like losers. Mafia bosses liked losers even less. Frank Sinatra was a winner, a winning bet. The Mafia bet big on Frank at the beginning of his career. The mob was in early on. Sinatra grooming him for stardom before anyone would give the poor son of a broken down boxer and illegal abortionist a chance when it mattered most. The Mafia used violence to clear the way for Frank and to cash in for themselves. There is a popular myth in our culture because Frank Sinatra's parents owned a bar in Hoboken, New Jersey where known members of the Jersey and New York mob hung out, that Frank made friends with some unsavory characters back in the day. And that this experience rubbed off on young Frank. And that's where Frank got his wannabe tough guy attitude. It's an attitude that many in Hollywood would joke about. An attitude that those who knew Frank best excused because of his immense fame. An attitude that has been reported to be nothing more than that. Just an attitude. Frank flew off the handle sometimes, sure, but that's just Frank. Oh yeah, Frank's got some tough guy friends. But hey, the nightclub business is a tough business. What do you expect? The entertainment world was run by the mob. Most entertainers came in contact with gangsters. Frank's okay. Frank fancies himself a tough guy like the tough guys he grew up with. Sure, but Frank's just a wannabe. However, the reality was Frank Sinatra wasn't just a wannabe. Frank Sinatra, without being an official made man, was not just friends with some tough guys from back in the neighborhood. Frank Sinatra was himself very much a gangster. Frank Sinatra held the woman by the neck, up against the wall. He was so angry he didn't realize he had her feet off the floor. His rage was blinding. At this moment he didn't even remember what she had done. But all that Jack Daniels. Frank couldn't not get what he wanted. He was Frank the Voice Sinatra, Charlie Lucky Luciano never had a weight. And they never said no to Richie the Boot Boyardo. Why did this half assed showgirl think she could disrespect him through the plate glass window she went. And Frank didn't care who saw it, didn't care even if the President of the United States, brother in law, the actor Peter Lawford, husband of Patricia Kennedy, saw it. Peter later went on record with this story about Frank and the working girl in the plate glass window. And fuck Peter and fuck his wife too, which Frank figured he would likely do again at some point, sleeping with the President's sister only further embedded Frank inside Camelot, which was a relationship Frank Sinatra cared about almost as much as his relationship with the mob, or the boys, as he called them. Peter Lawford wasn't the only one flapping his gums. Sammy Davis Jr. Talked to a Chicago radio station in the 60s and had the nerve to tell a DJ that, quote, I love Frank, but talent is not an excuse for bad manners. I don't care if you are the most talented person in the world. It does not give you the right to step on people and treat them rotten. This is what he does occasionally, end quote, in Chicago. Sammy said this on a Chicago radio station in Sam Momo, Giancana's town. Frank couldn't have this. Frank was just as indebted to Giancana now in the early 1960s as he'd been indebted back in 1946 to Giancana's then boss, Tony Accardo, the former bodyguard for Al Capone. But back in 1946, Al Capone was dying of syphilis in Miami, just 200 miles away from Cuba, where Capone, Chicago was being represented by his cousins Rocco and Charles Fietti. At this moment in 1946, those two gentlemen were on a plane seated next to Frank Sinatra, who had a bag at his feet that was stuffed with cash and a.32 revolver. All the boys knew the Faschetti cousins and everyone knew Frank Sinatra, big star that he was back in 46. And that was the genius of using Frank as the bag man. No one was going to search Frank Sinatra. Upon landing at Rancho Boyero's airport that December weekend among a flood of American mobs, soldiers and bosses. Vito Genovese, Frank Costello, Albert Anastasia, Joe Bonanno, Santo Trafficante Sr. And Carlos Marcello among them. The so called Havana Conference was set up in part to pay tribute to Charlie Luciano. Thus the bag of money and the Havana Conference was set up so Luciano and his partner Meyer Lansky could entice other crime bosses to invest in Havana's casinos. Cuban leadership, particularly the former president and military dictator Fludencio Batista, was beyond corrupt. And they had sold the country out to American mob interests. Havana was 100% owned by Luciano and Lansky, and now Luciano and Lansky were opening it up for business. That weekend there would be all manner of entertainment for the US Gangsters, showgirls, prostitutes, floor shows, depraved acts of bestiality, whatever they desired. And of course, a private performance by the biggest star on the planet at the time, their own Frank Sinatra. After his performance, the very much married Frank Sinatra settled into his suite at the Hotel Nacional with his girlfriend for the weekend, Alora Gooding. When Alora awoke after they had sex, she heard a loud banging outside, out the window. From beyond the terrace, she saw two guards sprinting straight for their room. What were they carrying? Frank? Get up. They have guns. They're coming to kill us. Frank sprung out of bed and went for his.32. The guards were now at the door, yelling in Spanish, and Alora grabbed the rifle they had in the room for extra protection. And there was more yelling and in a language Allora didn't not understand. Allura pointed the rifle and fired. One guard fell dead on the spot. Then another shot, this one from behind the guards, this one from the pistol of a hotel security man sprinting toward the clusterfuck in Frank Sinatra's suite. A clusterfuck just made worse due to the fact that the second shot killed the other guard at the door. It all happened before Frank's eyes had time to focus. He turned to his date. You killed that guy, alora protested. They were coming to kill us. They had guns. Frank looked down at the bloody mess in the doorway. Those weren't guns. Those were walkie talkies. The event was not sorted out by local lawmen, attorneys or judges. Justice was not sought or served. Frank never called the cops or his lawyer back in New York. Instead, Frank's gangster buddy sent Alora Gooding home quietly to the States while Mafia controlled Cuban soldiers cleaned up the mess. Frank Sinatra went about his business that weekend, reveling in the festivities, secure in the fact that the Mafia wasn't going to let anything as insignificant as a couple of dead Cubans submarine their investment in Havana or in their investment in one of their top earners, Him, Frank the Voice Sinatra. Foreign

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They say that in the Mafia, you're only as good as your next envelope. Meaning you're valued only by how much money you earn for your boss. Mafia soldiers don't earn salaries. They make their money criminally and they pay a portion of that money regularly to their bosses as tribute. In return, the boss protects them from from other violent mobsters and provides resources to help them commit their crimes. That's the deal. It's that simple. Frank Sinatra was a special case. He wasn't good with a gun. He wasn't a hitman, wasn't a safecracker or a second story man, wasn't an arsonist, extortionist or bookmaker. All standard Mafia occupations. Frank Sinatra was none of these things. Frank was a song and dance man. But just because Frank Sinatra's talent wasn't inherently criminal, it didn't mean Frank Sinatra didn't make money for the mob. He did. Frank Sinatra didn't just make money for the mob because they were friends he knew from back in the old neighborhood. Guys who may or may not have exploited him to act out of some sense of of childhood loyalty or otherwise. No, Frank Sinatra did favors for the mob and he earned for the mob because for all intents and purposes, Frank Sinatra was in the mob. I realize how ridiculous this sounds, but hear me out. Mafia soldiers, unmade men. They don't create a resume and sit down for job interviews with prospective mob families to obtain their jobs. Instead, they come up through the ranks in their respective neighborhoods, organically. Maybe a connected guy does a favor for a maid guy and the rising hoodlum pays him back with a favor of his own and thus A bond is created, further crimes are committed, and naturally the rising hood is given more opportunity until he finds himself in the activity employ of the mob, providing and collecting favors and now protection. And in return, earning regularly for himself and for his new boss. It's a documented fact that the Mafia financed Frank Sinatra's early career. They gave him cash for headshots, new suits, even walking around money. And in exchange for these favors, Frank Sinatra performed for the mafiosi. First in his parents Hoboken saloon where they hung out, and eventually in their nightclubs and on their touring circuits. And it is widely accepted as fact, basically admitted by Sinatra himself that in 1942 the mob sent Willie Moretti to pay a visit to bandleader Tommy Dorsey's home because Dorsey was preventing Frank Sinatra from making money. Dorsey had signed Sinatra to a bad contract, a contract that granted the bandleader the rights to one third of all of Frank's earnings for the rest of his life. William already put a gun to Dorsey's head. And if you believe the dramatization of the story in the Godfather, said to Dorsey, either your brains or your signature's gonna be on that contract. Dorsey, of course, signed, releasing Frank Sinatra from his contract. As far as severed horse heads and the beds of movie moguls, that's a bigger, blurrier dramatization. But again, as it pertains to Frank Sinatra's gangster bona fides, the outline of the story is true. But despite such protection, by the late 1940s, Frank's career was in serious jeopardy. Hollywood wanted nothing to do with him. He damaged his voice, he lost his his recording contract. His relationship with actress Ava Gardner was a tabloid nightmare and he was suddenly considered a has been. So once again, Willie Moretti stepped in to protect the Mafia's investment. Frank wanted the role of Private Maggio in the new film and production at Columbia Pictures, From Here to Eternity. And Moretti made sure Columbia studio boss Harry Cohn gave it to him. We cover the specifics of the this crime in our part one episode on Frank Sinatra. Needless to say, Frank got his way. The film was a hit. Sinatra won an Oscar for Best Supporting Actor. And just like that, his career was back in business. Now, did Frank Sinatra pay a weekly tribute to the mob like other Mafia soldiers? No, there's no evidence of that. But part of the deal when you're in the Mafia is answering when your bosses call and going to work when they tell you to. And there's plenty of evidence suggesting that the Mafia had Frank Sinatra on speed dial and that when the boys said jump, Frank asked, to the moon or higher? You tell me.

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[Jake Brennan]

given the volatile political situation in Cuba, the Mafia hedged their bets by building a second gambling empire, this one in Las Vegas, Nevada. They invested millions at a time when that really meant something. Frank Sinatra was asked to use his star power to attract other entertainers and thus gamblers to the Mob's new playground in Las Vegas. And Frank did just that. Once Cuba fell to Castro in 1959 and the mafia lost their Havana casinos, Las Vegas became even more important to the Mob's interests. Years before, Frank Sinatra had been asked to become a partner in a mob run establishment. A star like Frank, with an ownership stake in a Vegas hotel and casino, guaranteed big bucks for the bosses. And somehow, despite being in major debt to the IRS in the early 1950s, Frank Sinatra was allowed by the Nevada State Gaming Board to invest in the Sands Hotel and Casino and retain a 7.5% ownership piece. Mob boss Frank Costello was the majority owner and Meyer Lansky, Joe Adonis and Tony Accardo from Chicago, Sam Giancana's boss at the time, also owned stakes. In October 1953, Sinatra performed at the opening of the Sands and he packed them in the casino hotel was off the ground and running, and Sinatra was thus earning for the mob big time. The mob called upon Frank again, this time in 1960, and Frank once again came running. They wanted Frank to be part of another hotel and casino owner ownership group. This one was on the California Nevada state line, an existing but financially failing establishment called the Cal Neva. Frank's celebrity could infuse new life into the joint. Along with Frank, Sam Giancana, who by then was the boss of Chicago and one of the most prominent mafia leaders in the country, owned a massive stake in the hotel. The Cal Neva was a big hit on on opening night. In attendance were not only Sinatra and Giancana, but also the former United States Ambassador to the United Kingdom and one time mob bootlegger, Joseph P. Kennedy, and his son, the US Senator and presidential candidate, John F. Kennedy, along with his date, the most famous woman in the world at the time, Marilyn Monroe. Handsome Johnny Roselli was there too, of course, as were the FBI surveillance agents assembling what would become over the years, the biggest FBI file on any entertainer in history. And that entertainer was of course, Frank Sinatra. Just take a minute to appreciate this astonishing scene. You have one of the richest men in the world, Joseph P. Kennedy, a former ambassador, who by the way, was there with a date, not his wife, at the same party. You have his son, a senator, and a man who at that time had a massive national profile because he was running to become the next president. And he's married and he's there at the same party with his dad, who's with his mistress. And he, JFK is there with a date, even though he's married too, and his date is literally the most recognizable woman on the planet, Marilyn fucking Monroe. And, and, and, and the room is stacked full of known gangsters. Sam Giancana by that point was such a notorious criminal that he wasn't allowed to enter any casino throughout the state of Nevada. The Cal Neva was built on the state line and the structure straddled both states. Giancana was forced to stay on the California side only. This was not a secret. The gangsters, the corrupt former ambassador, the adulterous and brazen senator, the glamorous movie star mistress, with Frank Sinatra at the center of it all and the FBI listening and snapping pics. Sinatra's friend, the ruthless killer Sam Giancana, had something else in common with Senator Kennedy. They shared a girlfriend, knowingly with a woman named Judith Exner. Sam Giancano, Wiley Mo, Mafioso that he was, knew that he would one day be able to leverage Exner against jfk, a man Giancana was going to make the President of the United States with the help of Frank Sinatra. Just like the story of the Mafia freeing Sinatra from Tommy Dorsey's contract by making the bandleader an offer he couldn't refuse. We've come to accept the fact that Joseph P. Kennedy cheated his son's way into the White House by using Frank Sinatra as an intermediary between the Kennedy campaign and and the Mafia. And the Giancana fraudulently impacted the vote to help the Kennedys, first in the Democratic primary in West Virginia and then in the general election in Illinois. We look upon this story now as both a fact and as a cute, sly little historical anecdote. No serious historian disputes it. Yet today, any mention of electoral fraud sends people on both sides of the political spectrum into online hysterics. But again, we take it as gospel that the Democratic nominee used the Mafia to cheat his way into the White House with the help of our man, Frank Sinatra. We accept it because it's demonstrably true. Because that's how much power the Mafia had back in 1960. John F. Kennedy became President, and Sam Giancana and Frank Sinatra put him in the White House. Yet the President's brother, who is now the Attorney General, Robert F. Kennedy, the most powerful law enforcement officer in the country, would not stop his crusade to destroy Giancana and the Mafia. And RFK wouldn't stop because the FBI's J. Edgar Hoover played RFK. A recorded phone conversation between his brother, the married President, and his girlfriend, who was. Was also Sam Giancana's girlfriend. That conversation was recorded on a phone call that Judith Exner made to JFK from Sam Giancana's house. As far as Bobby Kennedy was concerned, Sam Giancana had to go. It was jail or bust. And Frank Sinatra, he was out as well. The President was, per his brother's instructions, under no circumstances allowed to carry on his friendship with Frank Sinatra. Frank Sinatra was too close to Sam Giancana. Frank was too gangster. But Frank wouldn't be denied. Frank couldn't be denied. Frank needed his relationship with the President so that he could remain in place as the conduit between the President and the Mafia and thus remain in good standing with Sam Giancana. You're only as good as your next envelope. But again, Bobby Kennedy wasn't having it. Bobby Kennedy increased his pressure on the mob. More surveillance, more subpoenas, more arrests, more deportations of mob bosses. Sam Giancana wanted to know where the Kennedy kids got their balls. Giancana got them elected, and now they betrayed him. The Kennedys, once elected, were supposed to put the mob back into Havana, not into prison, which is what RFK was coming dangerously close to doing. Sinatra was Giancana's only hope. The Mafia had given Frank so much, and now the Mafia really needed something from Frank. They needed Sinatra to get the Kennedys to back off. Frank tried, but Frank was out. So Frank threw a Hail Mary. Frank invited President Kennedy to his Palm Springs home for some much needed R&R. JFK loved Frank's palm Springs pad. It was private and filled with beautiful women. It's where JFK first slept with Marilyn Monroe. JFK said yes. He was coming to Frank's, and Frank was going to save the day. He'd talk to Jack, get Jack to talk to Bobby. To back off Sam and the boys, Frank built new quarters on his property for the Secret Service. Frank had a helipad installed. Frank spared no expense. And then Frank got ghosted by the President at the last minute. Bobby had prevailed. Making matters worse, JFK still went to Palm Springs, but he stayed at Bing Crosby's place. Bing was Frank's rival on the charts, and worse, a Republican. The humiliation. Frank Sinatra was out and Sam Giancana was pissed. Frank had no juice. Bobby Kennedy was on a warpath. Sam and the rest of the boys had no choice. And John F. Kennedy is now dead.

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[Jake Brennan]

Sixteen days after the Mafia conspired with the CIA to murder Frank Sinatra's friend, the sitting President of the United States, Frank sat in his Palm Springs home, wracked with grief and fearing that because he'd outlived his usefulness, that the Mafia was going to kill him next. That's when the unthinkable happened. Frank's son, Frank Sinatra Jr. Was kidnapped. The kidnappers weren't fucking around. Either they wanted $250,000 in cash, or little Frank was about to become dead. Little Frank. Frank knew that in moments of crisis, when you really need something taken care of the right way, like that mess back in Havana with the dead Cubans. When the chips are fully stacked against you, your first call is your most important call. Sinatra picked up the phone, and before he called his wife, before he called the cops or the FBI, he dialed the number of the one man he believed could help him get his son home safely. Mob boss Sam Giancana. Sam Giancana had his ways of making men talk. Most of them included Sam. Mad Sam Destefano, a sadistic enforcer. But this wannabe Nevada cowboy wouldn't talk. The boys from the Cal Neva pegged him as someone with info on the kidnappers. Frank Sinatra Jr. Just 19 years old at that point in time, launching his own career as a performer, was booked to perform at Harrah's Lake Tahoe Casino, about 12 miles from the Cal Neva. But instead. Room service. Frank Sinatra Jr. Opened the door to his hotel room and found himself staring down the barrel of a gun in his face on the ground. Within seconds, two intruders had Frank Jr blindfolded and bound. They escorted him out of the hotel at gunpoint, remarkably without any other hotel guests noticing, and whisked him away in their Chevy Impala. In Chicago, Sam Gianconda dispatched Jimmy the Weasel Fratiano to get to the bottom of where Frank the Voice, Sinatra's kid, was being held. The weasel turned up this cowboy, and Now Mad Sam DiStefano wanted to know if the cowboy preferred the ice pick or the blowtorch. The cowboy cowboyed up the blowtorch. It was. The cowboys screamed, seemed in agony. Back in Palm Springs, Frank Sinatra was understandably getting antsy. It had been nearly 18 hours since Junior had been kidnapped. The local authorities hadn't turned up any leads, and Giancana's boys weren't doing much better. The cowboy felt the ice pick pierce his skin above his kneecap, and he screamed in horror. Still, he didn't give anything up. By this time, Frank had decided to fly out to Reno himself to help in the search. Frank needed further assurance that his son was going to be returned safely. Frank hedged his bet, and when Frank landed, he immediately went to the FBI, to their makeshift command center to help the feds. In their efforts, Frank felt he couldn't count entirely on Sam Giancana. Mad Sam distefano switched from the ice pick to something more convincing. He laid the beaten cowboy down on the table and put his head in the vise. And while the cowboy urinated all over himself in fear, one of Mad Sam's muscle men swung a sledgehammer at his ankle and sent his foot into an ungodly 45 degree angle. This time there was no scream. This time the pain was so brutal, the cowboy could only huff out short breaths of air in uncontrolled bursts. Meanwhile, over in Reno, the kidnappers had made contact. They demanded a quarter million in cash. In Palm Springs, Frank's instincts kicked in. Ever the gangster, Frank called on his bagman experience and Brought a bundle of cash with him. On the FBI's recommendation, Frank put $250,000 in a suitcase. Frank was understandably injured, anxious as was Mad Sam. The cowboy wouldn't talk. The cowboy wouldn't give up. The whereabouts of Sam, Giancana's friend, Frank Sinatra's kid. The cowboy wants to be a cowboy. Time, then, for the cattle prod. Mad Sam had his own portable prod, customized for occasions just like this. The voltage was calibrated for maximum pain, but not enough to kill first. He placed the prod on the cowboy's eyelids. The cowboy's defiance was impressive. Then the inner thigh. The cowboy pleaded for Mad Sam to stop. He knew what the next stop on the torture trail was. The genitals. But still, he gave Mad Sam nothing other than pleading defiance. So Sam had no choice. The prod hit the Cowboy's testicles with 5 milliamps of current and 2000 watts. And still the near dead motherfucker gave up nothing. When Frank Sinatra hit the location for the drop back in Reno, everything went hooey. The kidnappers got antsy and split with Frank Sinatra Jr. Down to LA. Frank knew Giancana had nothing. And Frank began to suspect that Giancana himself was behind the kidnapping. A warning to Frank to keep his mouth shut about the Kennedy assassination. Frank had no choice. He needed to call in the big gun. To do so, he first called Peter Lawford. Frank knew he couldn't call Peter's wife, Patricia Kennedy, directly. He was still Persona non grotto with the Kennedys. But he knew he could get his friend Peter Lawford to get a word in with his wife. And he knew that there was a chance that Peter's wife would think of Frank fondly after the time they'd spent together. And thus, there was a chance that she would call her brother, the Attorney General of the United States, the man who controlled the FBI, Sam Giancana's Morgan mortal enemy, Robert F. Kennedy. That's exactly what happened. And despite whatever animus Bobby had toward Frank, Bobby pledged to use his power to help Frank get his son back. The message came back to Sinatra from RFK through Patricia, and then through Peter Lawford. And it was this. I know how Frank feels about me, but please tell him everything is being done and will get his boy back as soon as possible. While Giancana's man finished off the cowboy by impaling him with a meat hook through the rectum, and while Giancana's other men tortured and killed two more street tufts that they incorrectly suspected had information on the whereabouts of Frank Sinatra Jr. Bobby Kennedy flooded Reno and Los Angeles with more FBI agents. He ordered roadblocks at the borders of the state and random police checkpoints throughout California and Nevada. Bobby put the word out. No one was going home until Frank Sinatra got his son back. While the search continued, Bobby eventually called Frank himself to further assure him everything would be okay. And he was right. Three dipshits, two of whom were former high school classmates of Frank's daughter Nancy, eventually arrived at a separate drop point, this one in la, to pick up the ransom money. This time, the money was delivered by Bobby Kennedy's G Men, not by Frank Sinatra, the bagman. With the money in hand, the kidnappers freed Frank Sinatra Jr. Within 48 hours, all three kidnappers were arrested. Frank Sinatra did something that a lot of gangsters do when they're cornered, when their mafia families can't help them. He went to the feds for help. When Sam Giancana came up with bupkis, Frank cooperated with the government. Sure, he didn't rat anyone out, but he did do what some mafiosi would consider unthinkable. Something that meant many, many gangsters have been forced to do or otherwise face unthinkable truths. Life in prison, the death penalty. Two fates almost as bad as losing a child. It's hard to blame Frank, but then again, you and I aren't gangsters. Justice wasn't doled out by Sam Giancana, but by the US Court system. Barry Keenan, the ringleader of the kidnapping caper, got life in prison. He served four and a half years. Joe Amsler, the dumber of Barry's accomplices, caught a 75 year sentence. He served three and a half years. John Irwin, the most cooperative of the three, got 16 years. Ultimately, he served less than two. But three other men who had absolutely nothing to do do with the kidnapping were tortured and killed by Sam Momo Giancana on behalf of his friend, Frank the Voice Sinatra. No doubt Giancana shook this off as no big deal. It was amongst the Italians. He was helping out a friend, helping out a fellow gangster, which was without a doubt, a disgrace. Jake Brennan. And this is Disgraceland. All right, hope you dug this episode. Apple podcast listeners make sure to have auto downloads turned on so you guys never miss an episode of Disgrace. And this week's question of the week is, is, is Frank Sinatra the most gangster musician of all time? And if not, I want to know who is. Hit me up. Let me know. There are a lot of contenders. 6, 1, 790-66638 Leave me a voicemail or send me a text and be part of the show we play and read some of your answers on the afterparty bonus episodes like the one that's coming up right after this episode in your feed. I can also be reached on Instagram, Facebook x and and Disgracelandpodgmail.com leave a review for the show on Apple Podcasts or Spotify and you might win some free merch. All right, here comes some credits. Disgraceland was created by yours truly and is produced in partnership with Double Elvis. Credits for this episode can be found on the show notes [e-mail] if you're listening as a Disgraceland All Access member, thank you for supporting the show. We really appreciate it. And and if not, you can become a member right now by going to Disgracelandpod.com Membership members can listen to every episode of Disgraceland ad free. Plus you'll get one brand new exclusive episode every month, weekly unscripted bonus episodes, special audio collections, and early access to merchandise and events. Visit disgracelandpod.com membership for details. Rate and review the show and follow us on Instagram, TikTok, Twitter and Facebook Disgraceland Pod and on [e-mail] DisgracelandPod Rocka Rolla

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