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

Frank Sinatra was never just a pop star. In this second chapter of his story, Frank isn’t merely brushing shoulders with gangsters—he’s one of them. Backed by new research and newly released secret intelligence files, this episode unpacks how the Voice became a mafia asset. When Sinatra’s son is kidnapped, before he calls the police—he calls notorious gangster Sam Giancana. And what follows is one of the darkest, bloodiest chapters in music and organized crime history. Is Frank Sinatra the most gangster musician of all time? Tell Jake at 617-906-6638, [email protected], or on socials @disgracelandpod. To see the full list of contributors, see the show notes at ⁠⁠⁠⁠⁠⁠⁠www.disgracelandpod.com⁠⁠⁠⁠⁠⁠⁠ https://cms.megaphone.fm/organizations/c83125d2-8508-11ed-bd28-ff0aff7ee233/podcasts/efca2ef8-85f9-11ed-8fe3-bb208936046f/episodes/29bc673e-85fa-11ed-9d9c-cffe44583488/www.disgracelandpod.com. To listen to Disgraceland ad free and get access to a monthly exclusive episode, weekly bonus content and more, become a Disgraceland All Access member at ⁠⁠⁠⁠⁠⁠⁠disgracelandpod.com/membership⁠⁠⁠⁠⁠⁠⁠ https://disgracelandpod.com/membership. Sign up for our newsletter and get the inside dirt on events, merch and other awesomeness - ⁠⁠⁠⁠⁠⁠⁠GET THE NEWSLETTER⁠⁠⁠⁠⁠⁠⁠ https://mailchi.mp/doubleelvis/disgraceland-email-newsletter Follow Jake and DISGRACELAND: ⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠ https://www.instagram.com/disgracelandpod/ ⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠ https://www.youtube.com/@disgracelandpod ⁠⁠⁠⁠⁠⁠⁠X⁠⁠⁠⁠⁠⁠⁠ https://twitter.com/disgracelandpod (formerly Twitter) ⁠⁠⁠⁠⁠⁠⁠Facebook Fan Group⁠⁠⁠⁠⁠⁠⁠ https://www.facebook.com/groups/491024204626127/ ⁠⁠⁠⁠⁠⁠⁠TikTok https://tiktok.com/disgracelandpod To learn more about listener data and our privacy practices visit: https://www.audacyinc.com/privacy-policy Learn more about your ad choices. Visit https://podcastchoices.com/adchoices See omnystudio.com/listener https://omnystudio.com/listener for privacy information.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:01Speaker 00

  This is exactly right.

• 0:13Speaker 01

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• 0:44Speaker 02

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• 1:27Speaker 02

  Common cold, sinus infection, inflammation in the nose, flu or fluke-like symptoms, joint pain, or sore throat may occur. Carry on with fewer attacks and ask your doctor about Extenture. Learn more at extenture.com or call 1-833-393-3678.

• 1:44Jake Brennan?

  Disgrace Land is a production of Double Elvis.

• 2:04Jake Brennan?

  This is a story 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 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

• 2:48Jake Brennan?

  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 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.

• 3:32Jake Brennan?

  That was a preset loop from my Mellotron 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 8th, 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.

• 4:12Jake Brennan?

  On this episode, new research, secret files, illegal favors, torture, murder, and Frank Sinatra. I'm Jake Brennan, and this is DisgraceLand.

• 4:55Jake Brennan?

  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 Rogerio "Richie the Boot" Boyardo from New Jersey, who wasn't afraid to get his hands dirty.

• 5:40Jake Brennan?

  He was said to bury his enemies in his backyard. And then there was Angelo Gip DeCarlo, 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.

• 5:58Jake Brennan?

  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 Niri.

• 6:41Jake Brennan?

  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.

• 7:24Jake Brennan?

  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 Lavorcy 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 on Made Men of Influence are, of course, Tom Hagen and Mo Green.

• 8:10Jake Brennan?

  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 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

• 8:55Jake Brennan?

  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

• 9:34Jake Brennan?

  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.

• 10:19Jake Brennan?

  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 he 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 week, and they never said no to Richie the Boot Boy Ardo.

• 11:03Jake Brennan?

  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 and 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.

• 11:48Jake Brennan?

  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.

• 12:30Jake Brennan?

  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 Faschetti. 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 bagman. No one was going to search Frank Sinatra upon landing at Rancho Boyero's airport that

• 13:12Jake Brennan?

  December weekend, among a flood of American mobs, soldiers, and bosses: Vito Genovese, Frank Costello, Albert Anastasia, Joe Bonanno, Santo Trafficante Senior, 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, Flujenio

• 13:51Jake Brennan?

  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.

• 14:28Jake Brennan?

  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 Alora did not understand. Alora pointed the rifle and fired. One guard fell, dead on the spot.

• 15:13Jake Brennan?

  Then, another shot. This one from behind the guards, this one from the pistol of a hotel's 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.

• 15:56Jake Brennan?

  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.

• 16:56Speaker 01

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• 17:26Speaker 02

  Sponsored by GSK, the makers of Extenture. Depamocumab ULAA. If your asthma keeps interrupting, it may be time to try something else. Extenture is an ultra-long-acting prescription maintenance treatment for severe asthma, eosinophilic type, ages 12 and older. It isn't for sudden breathing problems. Extenture is the first and only add-on treatment that can help deliver protection from asthma attacks with two doses a year. Just one dose every six months. That's a lot of time for everything in between. Serious allergic reactions can occur. Get help right away for swelling of face, mouth, tongue, or trouble breathing. Don't change or stop medicines, including steroids, unless told by your doctor.

• 18:07Speaker 02

  Report if you have a parasitic infection, common cold, sinus infection, inflammation in the nose, flu or flulike symptoms, joint pain or sore throat may occur. Carry on with fewer attacks and ask your doctor about Extenture. Learn more at extenture.com or call 1-833-393-3678.

• 18:29Jake Brennan?

  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.

• 18:51Jake Brennan?

  In return, the boss protects them 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.

• 19:35Jake Brennan?

  Frank Sinatra didn't just make money for the mob because there 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 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.

• 20:20Jake Brennan?

  Maybe a connected guy does a favor for a made 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 actual employ of the mob, providing and collecting favors, and now, protection. And in return, earning regularly for himself and for his new boss.

• 20:48Jake Brennan?

  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' hobo can 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

• 21:32Jake Brennan?

  rights to one-third of all of Frank's earnings for the rest of his life. Willie Moretti 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 in 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.

• 22:16Jake Brennan?

  He damaged his voice. He lost 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 in production at Columbia Pictures from here to eternity. And Moretti made sure Columbia's studio boss, Harry Cohn, gave it to him. We cover the specifics of this crime in our Part 1 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.

• 22:59Jake Brennan?

  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."

• 23:31Speaker 04

  We'll be right back after this word, word, word.

• 23:38Speaker 01

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• 24:08Speaker 02

  Sponsored by GSK, the makers of Extenture, Depamocumab ULAA. If your asthma keeps interrupting, it may be time to try something else. Extenture is an ultra-long-acting prescription maintenance treatment for severe asthma, eosinophilic type, ages 12 and older. It isn't for sudden breathing problems. Extenture is the first and only add-on treatment that can help deliver protection from asthma attacks with two doses a year. Just one dose every six months. That's a lot of time for everything in between. Serious allergic reactions can occur. Get help right away for swelling of face, mouth, tongue, or trouble breathing. Don't change or stop medicines, including steroids, unless told by your doctor. Report if you have a parasitic infection, common cold, sinus infection, inflammation

• 24:53Speaker 02

  in the nose, flu or fluke-like symptoms, joint pain or sore throat may occur. Carry on with fewer attacks and ask your doctor about Extenture. Learn more at extenture.com or call 1-833-393-3678.

• 25:11Jake 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

• 25:53Jake Brennan?

  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.

• 26:38Jake Brennan?

  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 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 opening night, in attendance were not only Sinatra and Giancana,

• 27:20Jake Brennan?

  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.

• 27:39Jake Brennan?

  Handsome Johnny Risselli 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.

• 27:56Jake Brennan?

  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, the room is stacked full of known gangsters. Sam Giancana, by that point, was such a notorious criminal

• 28:41Jake Brennan?

  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 picks. 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 Giancana, wily mafioso that he was,

• 29:25Jake Brennan?

  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 the mafia, and that 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,

• 30:09Jake Brennan?

  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

• 30:49Jake Brennan?

  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 also Sam Giancana's girlfriend. That conversation was recorded on a phone call that Judith Exner made to JFK from Sam Giancana's house.

• 31:28Jake Brennan?

  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.

• 31:53Jake Brennan?

  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.

• 32:12Jake Brennan?

  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.

• 32:56Jake Brennan?

  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 and R. JFK loved Frank's Palm Springs pad. It was private, infilled with beautiful women. It's where JFK first slept with Marilyn Monroe. JFK said yes. He was coming to Frank's, and Frank was gonna save the day. He'd talk to Jack, get Jack to talk to Bobby to back off Sam and the boys.

• 33:29Jake Brennan?

  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.

• 33:44Jake Brennan?

  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.

• 34:08Jake Brennan?

  Frank had no juice. Bobby Kennedy was on a warpath. Sam and the rest of the boys had no choice, and John F. Kennedy was now dead.

• 34:21Speaker 05

  Now from Washington, government sources say that President Kennedy is dead.

• 34:27Jake 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 racked 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.

• 34:49Jake Brennan?

  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.

• 35:56Jake Brennan?

  Sam Giancana had his ways of making men talk. Most of them included Sam "Mad Sam" DiStefano, 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...

• 36:29Jake Brennan?

  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 fucking 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.

• 36:57Jake Brennan?

  In Chicago, Sam Giancana 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, and the cowboy screamed in agony.

• 37:24Jake Brennan?

  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.

• 38:06Jake Brennan?

  Frank felt he couldn't count entirely on Sam Giancana.

• 38:12Jake Brennan?

  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.

• 38:44Jake Brennan?

  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 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 fucking cowboy? Time then, for the cattle prod.

• 39:27Jake Brennan?

  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 and defiance. So Sam had no choice. The prod hit the cowboy's testicles with 5 milliamps of current and 2,000 watts,

• 40:10Jake Brennan?

  and still, the near-dead motherfucker gave up nothing.

• 40:19Jake Brennan?

  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 grata with the Kennedys. But he knew he could get his friend, Peter Lawford, to get a word in with his wife,

• 41:02Jake Brennan?

  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 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 we'll get his boy back as soon as possible."

• 41:48Jake Brennan?

  While Giancana's men 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 toffs 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.

• 42:33Jake Brennan?

  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.

• 43:04Jake Brennan?

  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 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.

• 43:45Jake Brennan?

  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 with the kidnapping, were tortured and killed by Sam "Momo" Giancana on behalf of his friend Frank "The Voice" Sinatra.

• 44:27Jake Brennan?

  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. I'm Jake Brennan, and this is DisgraceLand.

• 45:00Jake Brennan?

  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 Disgraceland. This week's question of the week 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. 617-906-6638. 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 after-party 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 [email protected]. Leave a review for the show on Apple Podcasts or Spotify and you might win some free merch. All right, here comes some credits.

• 45:45Jake Brennan?

  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 page at disgracelandpod.com. If you're listening as a Disgraceland All-Access member, thank you for supporting the show. We really appreciate it. 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

• 46:27Jake Brennan?

  Instagram, TikTok, Twitter, and Facebook @disgracelandpod and on YouTube at youtube.com/disgracelandpod. Rock-a-rola.

• 46:40Speaker 06

  He's a bad, bad man.

• 46:43Speaker 07

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• 47:12Jake Brennan?

  Hey guys, time to dust off your detective skills while unwinding in the Caribbean on Virgin Voyages' second true crime voyages. Back by popular demand, this five-night, adults-only escape sets sail March 20th, 2027 to Grand Turk in the Beach Club at Bimini. The difference between this year and last will be that I will be on the cruise this year, along with Zeph, and he and I will be taping a live version of DisgraceLand, along with podcast hosts from Exactly Right's Buried Bones, Podcast of the Year Award winners Wisecrack, and other fan favorites. Get on this cruise with us, guys, and enjoy live podcast recordings, behind-the-scenes storytelling, exclusive meet-and-greets, and immersive true crime programming throughout this one-of-a-kind voyage.

• 47:57Jake Brennan?

  Head over to www.virginvoyages.com/truecrime to secure your spot.

• 48:03Speaker 02

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• 48:47Speaker 02

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