Frank Sinatra Pt. 1: Frankie Is the Reason...That the President's Dead

Summary

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DISGRACELAND – Frank Sinatra Pt. 1: Frankie Is the Reason...That the President’s Dead

Host: Jake Brennan
Date: July 31, 2018

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Overview

In this electrifying episode of DISGRACELAND, host Jake Brennan delves into the tumultuous, drama-laden life of Frank Sinatra, illuminating how Old Blue Eyes’ personal ambitions, mob affiliations, and influence over American politics intertwined with—and, as Brennan provocatively contends, contributed to—the assassination of President John F. Kennedy. The narrative draws a direct line from Sinatra’s career low points and his mob-supported comeback, to his pivotal role in JFK’s election, and finally to the ultimate downfall of both Sinatra’s relationship with the Kennedys and Kennedy himself. Through cinematic storytelling, sharp insight, and dark humor, Brennan explores themes of celebrity, power, hubris, and the dangerous overlaps between the entertainment underworld and American history.

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Key Discussion Points & Insights

1. Introduction: Sinatra’s Myths, Power, and Hubris

• Sinatra’s reputation as a legend is interwoven with myth, crime, and charisma.
  • “He sent a tombstone to an unfriendly journalist… He’d rather be a Mafia don than the President…” (03:16)
  • He acted as a liaison between Hollywood’s elite and the underworld, especially in the company of gangsters and politicians.
• The central thesis: Sinatra’s boundless confidence blurred into hubris, which, through a web of relationships and favors, contributed to JFK’s assassination.
  • “An act that Frank’s confidence turned hubris was partly responsible for…” (04:11)

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2. Sinatra: The Original Pop Star

• Sinatra’s rise:
  • Broke the mold as the first teen idol, a singer whose emotional resonance gave him mass appeal.
  • His ability to seem both vulnerable and authoritative made him irresistible:
    • “The sound of his voice conveyed vulnerability and absolute authority all at once.” (05:12)
• Sinatra’s personal resonance for the host:
  • Brennan identifies with aspects of Sinatra’s persona, torn between street-smart authenticity and performative sophistication.
    • “In Sinatra’s voice, I also hear the contrived eloquence, the street kid who muscled his way into the smart set.” (06:31)
• Fall from grace:
  • By 1951, Sinatra’s career tanked; he was broke, divorced, out of work, and seen as washed up.

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3. Comeback: From Here to Eternity & Mob Connections

• Struggles to reclaim career:
  • Frank’s relentless lobbying to play Maggio mirrored his own outsider status.
  • The pivotal role in From Here to Eternity became an obsession.
• Mob intervention:
  • When Hollywood refused, Sinatra went to the Mafia—specifically Frank Costello and mob enforcer Johnny Roselli.
    • “Harry, if we have a problem here, you’re a fucking dead man.” – Johnny Roselli to Columbia Pictures’ Harry Cohn (15:29)
• Triumphant return:
  • Sinatra wins an Oscar (16:59)—a resurrection that made him feel “invincible… hubris, it’s only really hubris if you fail. Otherwise, it’s just confidence.” (17:44)
  • He poured his energy into prolific music releases—pioneering the “concept album” and dominating both film and pop music.

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4. The Sands, the Mafia, and Las Vegas

• Sinatra’s investments strengthened his mob connections:
  • Bought into the Sands Hotel—majority-owned by mob boss Frank Costello.
  • Sinatra’s presence turned the Sands into a hotspot, cementing his partnership with gangsters.
  • He happily ran mob errands, seeing himself as “just taking care of business.”
  • “If Frank had to jump on a plane to Havana with a suitcase full of cash from one of the boys… that wasn’t hubris. That was just Frank having the confidence to take care of business.” (21:13)

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5. Sinatra, the Kennedys, and Political Power

• The favor that changed history:
  • Joe Kennedy, JFK’s father, summoned Sinatra.
    • “There’s power and then there’s power. The Kennedys had it, Sinatra wanted it…” (25:57)
  • Task: Mobilize mob support in West Virginia to win the presidential primary for John Kennedy.
  • Sinatra delivers, calling in “the boys,” especially Sam Giancana, to rig votes and ensure JFK's victory.
    • “A couple thousand dead Democrats managed to crawl out of the Illinois cemeteries and into voting booths to cast their votes for Jack.” (28:23)
  • Sinatra’s role in Kennedy’s election stoked his sense of omnipotence and deepened his integration with both showbiz and the political elite.

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6. The Downfall: Sex, Betrayal, and Estrangement

• Sinatra and JFK’s excesses:
  • JFK and Sinatra bonded over women and parties; Sinatra became JFK’s fixer and “pimp.”
  • Jackie Kennedy despised Sinatra; Bobby Kennedy (JFK’s brother) regarded him as a liability.
  • The real disaster: JFK slept with Judith Campbell, mob boss Giancana's girlfriend—a direct result of Sinatra's introductions.
    • “You’re president, you’re married, you’re sleeping with any woman you want, and you decide to shack up with girlfriend of the most powerful mob boss in the country…” (29:38)
• Cut off:
  • The Kennedy administration severed ties with Sinatra after the scandal, devastating Frank and infuriating the mob, who felt betrayed after having delivered the presidency.

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7. Mob & CIA: Conspiring Against Kennedy

• The mob’s broken expectations:
  • The mob believed helping JFK would keep law enforcement off their backs; instead, Attorney General Robert Kennedy ramped up prosecution.
  • The mob’s Cuban casinos, vital sources of revenue, were lost after Castro’s revolution—the U.S., ironically, considered using Mafia muscle to topple Castro, but failed.
    • “Here it was, taking out a contract on the beard, Uncle Sam, no joke, gangster as fuck.” (33:31)
  • Frank, now on the outside, couldn’t help mitigate the tensions.
• The convergence of conspiracies:
  • Various groups—Mafia, CIA, anti-Castro Cubans, and disaffected elites—all saw Kennedy as a threat.
    • “What an epic fuck show.” (34:59)
  • Brennan narrates how self-interest and vengeance can turn uncoordinated discontent into dark, collective action.

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8. JFK Assassination: Fallout and Guilt

• Sinatra’s devastation:
  • On learning of JFK’s murder on November 22, 1963, Sinatra spirals into a deep depression and guilt.
    • “…he realized then that despite his clout, his friends, his confidence, he had been powerless to prevent it.” (37:46)
  • Brennan frames Sinatra’s grief as the ultimate reckoning of his lifelong hubris and influence.

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Notable Quotes & Memorable Moments

• On mob intervention:
  • “Harry, if we have a problem here, you’re a fucking dead man.” – Johnny Roselli to Harry Cohn, studio head (15:29)
• On Sinatra’s self-image:
  • “He’d rather be a Mafia don than the President of the United States.” (03:31)
• Hubris vs. confidence:
  • “Hubris. It’s a funny thing. It’s only really hubris if you fail. Otherwise, it’s just called confidence.” (17:44)
• On the Kennedy election's dirty underbelly:
  • “A couple thousand dead Democrats managed to crawl out of the Illinois cemeteries and into voting booths to cast their votes for Jack.” (28:23)
• On the assassination’s aftermath:
  • “When Frank Sinatra got word that his friend, the President of the United States, was murdered, he instantly knew why. And he realized then… he had been powerless to prevent it.” (37:46)

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Important Timestamps

• 03:16: Show proper begins—Sinatra’s wild stories and criminal exploits
• 05:12: Analysis of Sinatra’s unique appeal & vulnerability
• 09:50–14:13: Sinatra’s fall and relentless campaign for “From Here to Eternity”
• 15:20–17:44: Mafia intervention and Frank’s Oscar-winning return
• 18:00–21:33: The Vegas period, Sands Casino, and deepening mob ties
• 25:47–29:59: The Kennedy saga: Mob muscle, fixing elections, and power brokering
• 34:59: Conspiracy, self-interest, and the storm around JFK’s presidency
• 37:46: Sinatra’s reaction to Kennedy’s assassination and the shattering of his hubris

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Tone & Style

DISGRACELAND maintains a cinematic, pulpy, irreverent tone that oscillates between dark comedy and noir tragedy. The narrative voice is direct, occasionally profane, always dramatic, and loaded with a rock ‘n’ roll sensibility.

• “What an epic fuck show.” (34:59)
• Brennan’s storytelling eschews dry journalistic distance for immersive “truth-inspired” drama.

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Summary

Frank Sinatra’s story is told as a cautionary tale of ambition, criminal ties, and the dangers of unchecked hubris in the shadowy spaces between entertainment, organized crime, and political power. Through swaggering anecdotes, sharp psychological insight, and explosive historical moments, this episode offers a fresh, entertaining, and conspiratorial take on the tangled fate of a superstar and a president—hinting that Sinatra’s greatest legacy may be as much about chaos and consequence as about music and charm.

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Transcript

[Ryan Seacrest]

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[Public Investing Representative]

Support for the show comes from Public, the investing platform for those who take it seriously. On Public you can build a multi asset portfolio of stocks, bonds, options, crypto and now generated assets which allow you to turn any idea into an investable index with AI. It all starts with your prompt. From renewable energy companies with high free cash flow to semiconductor suppliers growing revenue over 20% year over year, you can literally type any prompt and put the AI to work. It screens thousands of stocks, builds a one of a kind index and lets you back tested against the S&P 500. Then you can invest in a few clicks. Generated assets are like ETFs with infinite possibilities, completely customizable and based on your thesis, not someone else's. Go to public.com podcast and earn an uncapped 1% bonus when you transfer your portfolio. That's public.com podcast paid for by Public Investing Brokerage Services by Open to the Public Investing Inc. Member FINRA and SIPC Advisory Services by Public Advisors llc. SEC Registered Advisor Generated Assets is an interactive analysis tool. Output is for informational purposes only and is not an investment recommendation or advice. Complete Disclosures available at public.comdisclosures

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[Jake Brennan]

Disgraceland is a production of Double Elvis. The stories about Frank Sinatra are crazy. He was once arrested for seduction. Seduction. He sent a tombstone to an unfriendly journalist as a warning. He broke into a home to steal away a cheating Marilyn Monroe from the arms of her lover as a favor to her estranged husband and Frank's pal Joe DiMaggio. Frank Sinatra is rumored to have couriered bags of cash for his friends in the mob, and he was quoted as saying he'd rather be a Mafia don than the President of the United States. And of course, he acted as a pimp for his friend John F. Kennedy. Francis Albert Sinatra, Old Blue Eyes, the son of Italian immigrants, pulled himself up from the streets of Hoboken, New Jersey, to the top of the entertainment world to become, quote, unquote, chairman of the Board. Along the way, he made and relied on some interesting friends, entertainers, politicians and gangsters. Friends whose power, mixed with Frank's inherent confidence made Frank believe he was 10ft tall and could accomplish whatever he set his mind to. And one of the things Frank Sinatra accomplished was the making of some of the greatest music ever recorded. And that music you heard at the top of the show, that wasn't great music. That was a preset loop from my Melotron called Moving Bass piano, moving strings, MK2. And I played you that loop because I can't afford the license for I'm Leaving it up to you by Dale and Grace. And why would I play you that specific slice of greasy duet cheese? Could I afford it? Because that was the number one song in America on November 22, 1963. And that was the day that Frank Sinatra's pal, John F. Kennedy, President of the United States, was assassinated. An act that Frank's confidence turned hubris was partly Responsible for on this episode, JFK moving, string cheese, the Mafia, hubris and Frank Sinatra. I'm Jake Brennan, and this is disgrace. To understand Frank Sinatra the man, you have to understand Frank Sinatra the performer. He was the first teen idol, he was the first pop star, and he was unlike anything anybody had heard or seen before. His command of his voice, stage and camera was entirely unique. Sure, Bing Crosby paved the way, but Frank blazed a new path and the sound of his voice conveyed vulnerability and absolute authority all at once. The result? A level of intimacy and relatability that worked on women and men alike. And we've worn out the old showbiz descriptor. Men wanted to be him and women wanted to sleep with him. But it was invented to describe Frank Sinatra. Watch any of his live performances, from his early days with the Tommy Dorsey Orchestra to his retirement concert in Los Angeles in 1971, and you'll notice an undeniable confidence and electric masculinity. We hear what it is to be a man, the good and the bad. To me personally, when Sinatra speaks, I hear in his slang a lack of self awareness, a neighborhood tough guy with a big heart. More specifically, I hear the unrefined toughness and emotional generosity of my stepfather. Someone strong enough to let you in unafraid, comfortable in his own skin. And in Sinatra's voice, I also hear the contrived eloquence, the street kid who muscled his way into the smart set. I hear my biological father, a man who, like Sinatra, had the intellectual sand to surround himself with educated men, even though he himself was never schooled beyond the 12th grade, but who, no matter how many books he reads, when he speaks will always sound like he's reaching and will thus box you out and make you feel like you need to continuously do better to gain his approval. And the voice sounds slightly uncomfortable, afraid of being found out that he snuck into the party. And through all of Frank's music, you hear a loneliness, something we can all relate to and something Frank used humor to mask. He would have been the class clown had he ever gone to class. So it was no surprise that it was a wise ass comment in 1950 about MGM Studio head Louis B. Mayer that got Frank fired from MGM and spelled the end of his career. Well, the wise ass comment. On top of poor film reviews, lagging record sales, a voice that was failing from overuse and a decade of bad press due to his body and sometimes violent public behavior, by 1951, Sinatra was out. He went from being a street kid from Hoboken New Jersey to the first teen idol, to being one of MGM's biggest Hollywood stars, to being broke, busted, divorced from his first wife, Nancy, perpetually at odds with his tempestuous lover Ava Gardner, and right back where he started at the bottom. It got so bad that Sinatra, who a few years earlier couldn't go anywhere without mobs of screaming girls chasing him down, could now be seen roaming around Times Square at 4am alone and drunk. Beat cops would find him passed out in the doorways and try to move him along. He couldn't even get arrested. Literally. Something had to give. Frank knew he wasn't over. He might not have had any cash, but he still had confidence. And just like every woman he'd ever met, except for maybe Ava, Frank knew America would take him back. Hollywood was abuzz about the script adaptation of the bestselling novel From Here to Eternity. And there was one role that Frank knew would reignite his career. Maggio, the skinny guinea with the chip on his shoulder from Brooklyn, which like Frank's Hoboken, was at the time a world away from Manhattan. Maggio's outsider status, his insecurities, they were characteristics that Frank Sinatra understood on a molecular level.

[Ryan Seacrest]

Hey, it's Ryan Seacrest for Albertsons and Safeway. It's Stock up Savings time now through March 31st. Spring in for store wide deals and earn four times the points. Look for in store tags to earn on eligible items from Lindor, Chips Ahoy, Gatorade, Host, Ziploc and Zoa. Then clip the offer in the app for automatic event long savings. Stack up those rewards to save even more. Enjoy savings on top of savings when you shop in store or online for easy drive up and go pick up or delivery restrictions apply. See website for full terms and conditions.

[Public Investing Representative]

Support for the show comes from Public, the investing platform for those who take it seriously. On public you can build a multi asset portfolio of stocks, bonds, options, crypto and now generated assets which allow you to turn any idea into an investable index with AI. It all starts with your prompt. From renewable energy companies with high free cash flow to semiconductor suppliers growing revenue over 20% year over year. You can literally type any prompt and put the AI to work. It screens thousands of stocks, builds a one of a kind index and lets you back test it against the S&P 500. Then you can invest in a few clicks. Generated assets are like ETFs with infinite possibilities, completely customizable and based on your thesis, not someone else's. Go to public.com podcast and earn an an uncapped 1% bonus when you transfer your portfolio. That's public.com podcast paid for by Public Investing Brokerage Services by Open to the Public Investing Inc. Member FINRA and SIPC Advisory Services by Public Advisors, llc. SEC Registered Advisor Generated Assets is an interactive analysis tool. Output is for informational purposes only and is not an investment recommendation or advice. Complete Disclosures available at public.comDisclosures we all

[Amy Anda]

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[Jake Brennan]

But Columbia Pictures was producing the film and studio boss Harry Cohn hated Frank Sinatra wouldn't be deterred. He wrote Cohn countless letters detailing the many reasons why he was perfect for the role, signing them all Maggio. But Cohn wouldn't budge. Cohn's authoritarian approach to running one of the biggest movie studios on the planet was modeled after fascist dictator Benito Mussolini's approach to running Italy. Cohn had met Mussolini years earlier, before the outbreak of World War II, and was so impressed by him that he remodeled his own office to match the dictator's, designed to achieve maximum leverage over his guests. His desk sat up high on a daisy to intimidate. But the man sitting across from Con was anything but intimidated. Quite the opposite, actually. He was the intimidator. He was Johnny Roselli, a fearsome Mafia enforcer for the Chicago outfit. Sinatra had a friend with high level mob connections appeal to his bosses higher up the Mafia food chain. Sensing a future as of yet unknown opportunity, and perhaps out of genuine affection for old blue eyes, the Mafia via the boss himself, Frank Costello decided to bet on Frank when no one else would, to buy low, as it were. And so Johnny Roselli was dispatched to help sort out the Sinatra situation. Roselli spoke with authority. Harry, give Frank the part. It's perfect for him. Cohn wasn't easily cowed. I know it's perfect for him, which is why he ain't getting it. Sinatra is washed up and he's going to stay washed up. Roselli figured he'd try the soft touch once more. Harry, give the kid a chance. Remember not so long ago when you needed a second chance, who was there for you? We was there for you. Cone was losing patience. John, if we have a problem here, I'm going to have to make some phone calls. Johnny Roselli stood up, hopped up on the dais, put both hands on Cone's shoulders, leaned over into an inch of his face and let it be known that he was through dicking around. Harry, if we have a problem here, you're a fucking dead man. In a little over 24 months, Frank Sinatra could be seen sprinting down the aisle of Pantages theater at the 26th annual Academy Awards to accept the Oscar for Best Supporting Actor for his portrayal of Maggio in the Harry Cohn produced From Here to Eternity. Frank Sinatra was back. Frank Sinatra was never wanting in the confidence department. Even when his career was over, even when he was suicidal, over the only woman to really reject him, Ava Gardner. Even then, the too short, too skinny son of Italian immigrants from Hoboken had confidence to spare. So when he came back, when he raised that Oscar over his head and proved to the world that he could do what only one man before him, Jesus H. Christ, had been able to do, come back from the dead, well, he felt invincible. Like he could do anything. Hubris. It's a funny thing. It's only really hubris if you fail. Otherwise, it's just called confidence. But Frank Sinatra was no longer failing. He was redefining the meaning of success with one hit after another through a diverse portfolio of entertainment projects. Following the 1953 Oscar, Frank poured himself into his work. He ripped off a dizzying array of impressive musical releases under a new recording contract with Capitol Records. Inspired by the genius arrangements of musical director Nelson Riddle, Sinatra took control of the charts, minds and hearts of young lovers everywhere with a string of truly great long players. Songs for young lovers, Swing Easy, and then, in my opinion, his best album, in the wee small hours of the Morning, an album where Frank Sinatra invented the concept of the concept album. Subsequent LPs released in the 50s, a swinging affair, Come Fly With Me and Frank Sinatra Sings for Only the Lonely, would all contain songs that would become so popular they'd eventually become standards of the American pop canon. Sinatra's musical output alone was staggeringly prolific. But with his Oscar still fresh in the minds of Hollywood producers, he also moved quickly to keep his film career moving. He starred alongside Doris Day in Young at Heart, Grace Kelly in High Society, Marlon Brando in Guys and Dolls, and was nominated for another Oscar for his portrayal of a heroin addict in the man with the Golden Arm. Before long, he was the highest paid actor in Hollywood. And he kept moving like a shark in a side of or suit. Slowing down meant looking in the mirror and facing that ever present loneliness. So work, work and more work. Frank took part of his earnings and bought a plane, using it to charter him and his friends Dean Martin, Shirley MacLaine, Humphrey Boger to his new playground in the desert, Las Vegas, where Frank took another piece of his bread and invested in the Sands Hotel and Casino. The property whose majority share was owned by Frank's old friend Mob Boss Frank Costello, the same mafioso who pulled Harry Cohn's strings via Johnny Roselli to get Frank the Oscar winning role in From Here to Eternity. Hanging out with mobsters was old hat for Sinatra. Back in Hoboken, his father made ends meet as half a wise guy. Frank had long referred to them as the Boys. And by the time he entered the entertainment industry, where the nightclubs, dance halls and concert venues were controlled by the Mafia, Frank was used to hanging around with gangsters and not shy about asking for or returning favors for them. Frank was enamored of them. Gangsters had real power and they were a lot of fun. And Frank was no stranger to a good time. Which is why the investment in the Sands made sense. Plus, the gangsters really did like Frank. He was like them, Italian from the streets. And he didn't take shit off no one. Plus, that voice, those eyes. Dude was a pussy magnet. But he attracted more than just women. Everyone wanted to be around Frank. He was a star. Star. With Frank owning a piece of the Sands with his name association, the joint was packed every night. Money poured in. Sure, every once in a while, Frank had to do a little favor for one of the boys, but it wasn't bad. Deliver a message here or there, convince a fellow star to join him at the Sands for a reduced rate. None of it seemed extraordinary because Frank Sinatra himself was extraordinary. If Frank had to jump on a plane to Havana with a suitcase full of cash from one of the boys and make sure it landed in the right greasy hand, well, that wasn't hubris. That was just Frank having the confidence to take care of business.

[Public Investing Representative]

We'll be right back after this. Word.

[Jake Brennan]

Word.

[Public Investing Representative]

Word.

[Ryan Seacrest]

Hey, it's Ryan Seacrest for Albertsons and Safeway. It's stock up savings time now through March 31st. Spring in for storewide deals and earn four times the points look for in store tags to earn on eligible items from Hunts, Nerds, Pillsbury, Lowry's, Breyers, Quaker and Culture Pop. Then clip the offer in the app for automatic event long savings. Stack up those rewards to save even more. Enjoy savings on top of savings. When you shop in store or online for easy drive up and go pickup or delivery restrictions apply. See website for full terms and conditions.

[Public Investing Representative]

Support for the show comes from public, the investing platform for those who take it seriously. On public, you can build a multi asset portfolio of stocks, bonds, options, crypto and now generated assets which allow you to turn any idea into an investable index. With AI it all starts with your prompt from renewable energy companies with high free cash flow to semiconductor suppliers, growing revenue over 20% year over year. You can literally type any prompt and put the AI to work. It screens thousands of stocks, builds a one of a kind index and lets you back test it against the S&P 500. Then you can invest in a few clicks. Generated assets are like ETFs with infinite possibilities, completely customizable and based on your thesis, not someone else's. Go to public.com podcast and earn an uncapped 1% bonus when you transfer your portfolio. That's public.com podcast paid for by Public Investing Brokerage Services by Open to the Public Investing Inc. Member FINRA and SIPC Advisory Services by Public Advisors llc. SEC Registered Advisor Generated Assets is an interactive analysis tool. Output is for informational purposes only and is not an investment recommendation or advice. Complete disclosures available at public.com disclosures let's talk personal Style.

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[Jake Brennan]

the mafia, getting sent for is nerve wracking. It usually means you're being deployed to whack someone or you yourself are about to get whacked. In politics, getting sent for usually means you're being deployed to kiss someone's ass or you yourself are about to get your ass kissed. Which never comes without strings. Which is why when the half politician, half gangster Joseph P. Kennedy, father of Senator and candidate for President of the United States John F. Kennedy, sent for Frank Sinatra, Frank was doubly concerned. What did the old man want? Frank didn't know. All he knew was that he was an admirer of the son Jack. Young, articulate, good looking and that had a hair and that smile you could see from space. Charisma for days. And like Frank, Catholic. Just think, a non WASP with a legit shot at the White House. In 1960, Frank boarded his jet and took off for the Kennedy compound in Hyattisport, Massachusetts. Frank was in awe of the Senator's father. Sinatra's own father worked for JFK's dad back in the day, running rum through the swamps of Jersey during Prohibition. And so here Frank sat looking up at the bootlegger turned ambassador from across the desk like a common laborer being put to task by management. There's power and then there's power. The Kennedys had it, Sinatra wanted it, and what Joe Kennedy wanted was a favor. The message was direct. His son was going to lose the West Virginia primary to Democratic were Hubert Humphrey and that couldn't happen. Losing West Virginia meant losing the nomination and the Kennedys weren't in the Business of losing. Joe needed Frank to get Frank's Mafia pals to roust up enough votes in West Virginia to deliver a win for Jack. Sure, Ambassador, no problem. I'm sure the boys would be happy to help. Frank hightailed it to Miami for a round of golf with Sam Giancana, AKA Momo, AKA the ruthless Chicago mobster who controlled the Midwest and West Virginia. A Sands regular and a friend of Frank's, who at the time was renting out space way up his ass to the Ambassador's other son, Senator Robert F. Kennedy, who'd been making it his business to crack down on organized crime. So Giancana saw the obvious play. Help Jack the haircut, win West Virginia and evict Bobby, the pit bull, from out his fight. And with that, it was done. Sort of. The election was a nail biter. Jack had secured the nomination, but the Republican nominee, Richard M. Nixon, was a formidable candidate and almost as dirty as the Kennedys. Almost. It all came down to Illinois, Giancana's home state, rich with electoral votes and rife with corruption. It was easy in the end. A couple thousand dead Democrats managed to crawl out of the Illinois cemeteries and into voting booths to cast their votes for Jack. The Kennedys were going to the White House, and Sinatra helped put them there. What couldn't Frank do? Take it easy. That's what the party was on. There was one man in America who was a bigger pussy hound than Frank Sinatra, and that was Jack Kennedy. The two were a formidable pair. Frank hosted Jack at his Palm Springs residence and stocked the place with hookers, booze, gourmet food, celebrity friends, and whatever else he thought his new politician pal wanted. And Jack loved it. And the remote location, far beyond the judgy eyes of the press or his wife, meant he could relax, hang out by the pool, gossip with showgirls, smoke a joint or two, get laid whenever it was great. But when Jack entered the White House, Sinatra was starting to be seen as a liability. Jackie, Jack's wife, hated him. I mean, why wouldn't she? Frank was basically her husband's pimp. But more damning was the wrath of Jack's brother, now Attorney General Bobby Kennedy, who learned that Jack, by introduction of Frank, was sleeping with Judith Campbell, girlfriend of mobster Sam Giancana, Bobby's nemesis. Talk about hubris. You're president, you're married, you're sleeping with any woman you want, and you decide to shack up with girlfriend of the most powerful mob boss in the country who is also the sworn enemy of your brother. The Attorney General, AKA the top cop in the land. Yikes. Despite Frank's efforts in helping elect jfk, the Kennedys cut him off. Frank was devastated. He loved Jack. He didn't blame him though. He blamed Bobby. Frank was hurt, angry. But you know who was even more angry? Sam Giancana. Giancana thought that helping the Kennedys would get authorities out of his hair. But no. Since Jack the haircut became President, the heat got hotter. The Mafia felt it everywhere. Tales, raids, wiretaps. And Giancana was losing face. After all, he helped get these snot nosed Irish punks into office. And here they were, endlessly harassing him, making him look like a jerk off sleeping with his woman. But somehow the Mafia had an even bigger problem. All the casinos they owned in Havana, Cuba had just been shut down, abruptly nationalized by the communist Fidel Castro during his recent rise to power. And this meant a massive portion of the mob's revenue had vanished overnight. In true to form, the Kennedys were no help. They'd botched the Bay of Pigs invasion, a CIA backed military effort to oust Castro from power, boot the commies from the western hemisphere and restore democracy and the Mafia's reign in Cuba. But of course, Kennedy would only commit to sticking his dick in halfway. How out of character. And the invasion failed. But the Kennedys didn't care. They thought, as did Sinatra, that they had the world on a string. But some very dangerous people were starting to get dangerously upset. And their confidence was about to turn to hubris. Johnny Roselli couldn't believe his life. Never a dull moment for a mid level hood like Roselli. The action was non stop. The girls, the gambling, the graft, it got to be ordinary. But this, this was very much extraordinary. Roselli was seated across from two CIA spooks who are offering him and the Syndicate, the American Mafia, cold hard cash to whack out Fidel Castro. Who'da thunk? The United States government wanted Castro gone just as badly as the mob did. So here it was, taking out a contract on the beard, Uncle Sam, no joke, gangster as fuck. But try as they would, Roselli and his American mob cohort, Santa Trafficante, Frank Costello and Sam Giancana could not get to Fidel. And every day that communist bastard stayed in power was another day of lost millions for the boys. And making matters worse, the Kennedy administration, through the efforts of Bobby's Justice Department, kept the heat up on organized crime. The Mafia was getting shafted both ways, coming and going. And after the Bay of Pigs debacle, President Kennedy had the balls to declare war on his own CIA. He felt the CIA hung him out to dry with the botched invasion and now seemed content to let Castro remain in power so long as the Soviets were kept out of the hemisphere. The Soviets, Communist Cubans, the anti Castro Cubans, the CIA, the Mafia, not to mention capitalist industrialists, Republicans and papal fearing wasps and racists from the American south, all suddenly found their own self interest coalescing around their mutual hatred of the Kennedys. What an epic fuck show. Frank Sinatra watched it all from the sidelines while his Mafioso buddies tried unsuccessfully to get him to get his so called friend the President to call off his dogs. But it was useless. Frank was out. The Kennedys didn't really. Or so they thought. So they pressed on, kept the heat up on the Mafia, kept Castro in power through their inaction, kept up their pledge to dismantle the CIA and kept Frank Sinatra at bay. Which was likely their biggest mistake. Had they kept Frank in the loop, Frank would have been able to impress upon them just how angry they were making the mob and the CIA. But when you're young, rich, beautiful, powerful and can have anyone you want, do anything you want and you believe in your own bullshit. At some point it became clear to both the Mafia and the CIA that if they couldn't use their combined efforts to get rid of the beard, then they should use their combined efforts to instead get rid of the haircut. There is an old Sicilian saying that if you want to kill a dog, you don't cut off his tail, you cut off his head. Great plots, conspiracies take time to develop, but in the end come together shockingly quick. So quick that the players in the scheme seldom know that they're even playing. Conspiracies are thought to be vast plots conducted from on high by evil villains and schemers. But in reality, conspiracies happen when mutual, mutually aggrieved groups of people simultaneously lock into one powerful shared sentiment, usually greed or vengeance, and are so compelled by their own self interests that their destinies become self fulfilling enough to propel them all collectively toward a singular goal. In this case, for the Mafia and the CIA, it was the elimination of an existential threat to their survival. The Kennedys. If the Mafia was going to survive, if the CIA was going to survive, JFK had to go kill the President of the United States. Now that's hubris. Unless of course you get away with it, then it's just confidence. Dallas, November 22, 1963. Game day. It had been a long time coming. No one, even those involved, truly knew what was happening. They just knew they had a part to play, and that later, if everyone moved in the right direction at the right time, their problems would go away. And that's what happened. When Frank Sinatra got word that his friend, the President of the United States, was murdered, he instantly knew why. And he realized then that despite his clout, his friends, his confidence, he had been powerless to prevent it. After the assassination, Frank crawled into an endless bottle of Jack Daniels and sunk into a deep depression. He he became one of those sad sack characters in one of his songs. What was it that had brought him to this point, this lowest of lows? Hubris mourning the loss of a man he deeply admired and counted as a friend, despite his recent estrangement. Yes, hubris was to blame for this, just as it was to blame for the demise of Jack Kennedy, a man who could not see through the blinding light of his own powerful entitlement. But for Sinatra, this pit of grief, guilt, self doubt, and oh, too familiar loneliness could only be vanquished by real inner strength, real confidence. Or maybe all it would take would be a favor from one of the boys. I'm Jake Brennan and this is Disgrace. 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 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 Disgracelandpod and on YouTube at the end. YouTube.com Disgracelandpod Rocka Rolla

[Danielle Robaix]

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[Jake Brennan]

This episode is brought to you by Choiceology, an original podcast from Charles Schwab,

[Public Investing Representative]

hosted by Katie Milkman, an award winning

[Jake Brennan]

behavioral scientist and author of the bestselling book how to Change. Choiceology is a show about the psychology and economics behind our decisions. Hear true stories from Nobel laureates, authors, athletes and everyday people about why we make the choices we do and how to make better ones. To help avoid costly mistakes, listen to [e-mail] podcast or wherever you listen.