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What if the most powerful man in the
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world, the president of the United
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States, and the most dangerous man in
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the country, the head of the Chicago
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mob, was sharing a secret, a secret so
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explosive it could have destroyed them
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both. And that secret was a woman. This
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is the story of the unbelievable love
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triangle that connected the White House,
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the Hitter mob, and Hollywood, and how
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one woman's life became tangled in a web
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of power, politics, and peril that
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threatened to bring them all crashing
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down. Section one, the president. In the
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late 1950s, America was on the verge of
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something new. And no one seemed to
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capture that hopeful, ambitious energy
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better than John F. Kennedy. He was the
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handsome war hero, the charismatic
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senator from a legendary political
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family. He had a smile that could light
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up a room and a way with words that
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could inspire a nation. By 1960, he was
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aiming for the highest office in the
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land, the presidency. The Kennedy name
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was practically American royalty, a
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carefully crafted image of glamour,
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intelligence, and public service. It was
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a brand, and that brand was Camelot. But
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behind that perfect gleaming facade, the
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Kennedy operation was a machine built
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for one thing, ruthless political
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The family patriarch, Joseph P. Kennedy,
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was a man famous for his cutthroat
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business deals and his deep
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understanding of how power really worked
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in America, from the boardroom to the
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backroom. He'd allegedly built
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relationships with underworld figures
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during prohibition and knew that you
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don't always win elections with just
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handshakes and speeches. As JFK launched
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his presidential campaign, the race
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against Richard Nixon was looking razor
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thin. Key states, especially those with
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powerful union bosses and dug in
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political machines, were going to be the
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battlegrounds. The Kennedes needed every
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single advantage they could get, even if
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that meant reaching into the very
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shadows they publicly denounced. And
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Jack Kennedy himself, the aspirational
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figure for a whole new generation, had a
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reckless appetite for secrets,
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especially when it came to his private
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life. His list of alleged affairs was
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long and legendary, a habit that
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constantly risked exposing the pristine
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image of Camelot to a devastating
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scandal. It was this mix of ambition and
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appetite, of public ideals and private
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risks, that set the stage for a
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collision with worlds far beyond the
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polished halls of Washington DC. Section
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two, the mob boss. A world away from the
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campaign trail. In the smoky back rooms
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of Chicago, a very different kind of
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power belonged to one man, Salvatore Sam
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Born to Sicilian immigrants, Gian Carana
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had climbed the bloody ladder of
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organized crime, starting as a teenage
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getaway driver and rising to become the
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undisputed boss of the Chicago outfit,
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the criminal empire Al Capone built.
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Known for his brutal temper and sharp
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mind, Gian Connor was a man of
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incredible influence and violence. He
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controlled a massive network of illegal
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gambling, liquor distribution, and
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extortion rackets. But his reach didn't
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stop at the underworld. By the late
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1950s, Gianana had pushed the outfit's
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influence into the glittering casinos of
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Las Vegas and the sunny shores of Latin
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America. More importantly, he had his
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hooks in both politics and
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Gian Carana got it. Real power wasn't
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just about violence. It was about
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influence. His connections to powerful
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labor unions gave him the ability to
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swing elections, a tool he was happy to
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use for the right price. His
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relationship with Hollywood was just as
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calculated. He was a regular at
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celebrity parties, rubbing shoulders
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with the biggest stars of the era. This
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wasn't just for fun. It was business.
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His control over unions like the
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Teamsters meant he could shut down a
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movie studio with a phone call and his
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reputation for violence made sure
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Hollywood's elite treated him with a mix
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of fear and respect. Sam Gianana had
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become a public figure, a celebrity
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gangster who loved the limelight, a
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trait that made his more secretive
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partners very nervous. He was known for
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his relationships with famous women, but
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it was another lesserknown woman who was
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about to connect his dangerous world
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directly to the Oval Office. Section
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three. The starlet out in the sprawling
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sundrenched suburbs of Southern
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California. Judith Eileene Katherine
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Immore was living a life that felt a
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million miles away from Washington
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politics and Chicago mob wars. Growing
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up in the wealthy neighborhood of
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Pacific Palisades, she was raised in a
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world right next to celebrity, close
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enough to feel its magnetic pull. After
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a short marriage to actor William
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Campbell in the 1950s, she became Judith
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Campbell, a beautiful and charming
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divorcee making her way through the
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glamorous social scenes of Hollywood and
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Las Vegas. She was the kind of woman who
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attracted powerful men. Moving through a
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world of exclusive clubs, highstakes
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casinos, and private parties where the
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lines between fame, power, and money
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were intoxicatingly blurred. Judith
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wasn't a movie star or a politician. She
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didn't have any official power. But in
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the ecosystem of 1960s America, her
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beauty and charm were a currency all
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their own. She was about to be thrown
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into the center of a storm, becoming the
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living, breathing link between the
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country's greatest hopes and its darkest
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secrets. Her journey would start with an
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introduction from a man who moved easily
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between all these worlds, the one and
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only Frank Sinatra. Section four, the
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connection. Frank Sinatra was more than
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the world's most famous singer. He was a
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cultural force and a power broker. The
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chairman of the board partied with movie
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stars in the Rat Pack. Campaigned for
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politicians and according to a mountain
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of FBI surveillance, kept a close and
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useful friendship with mobsters like Sam
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Gianana Sinatra was the bridge. the guy
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who could connect the dots between
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Hollywood glamour, Washington power, and
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mob business. And in 1960, he made two
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introductions that would change
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everything. On February 7th, 1960, in
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the neon glow of Las Vegas, just weeks
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after JFK had announced his run for
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president, Frank Sinatra introduced
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Senator Kennedy to Judith Campbell. The
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spark was instant. For the next month,
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Kennedy and Judith were on the phone
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almost every day, a fact later confirmed
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by White House phone logs. Their first
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physical encounter happened on March the
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7th at the Plaza Hotel in New York City,
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the night before the New Hampshire
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primary. This kicked off an 18-month
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affair that would continue even after
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Kennedy was in the White House with
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secret meetings in New York, LA, and
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even inside the White House itself. But
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Sinatra wasn't done playing matchmaker.
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He also introduced Judith to his friend
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from Chicago, Sam Gianana. Soon, Judith
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found herself in the incredible position
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of being the mistress to both the
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leading presidential candidate and one
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of the country's most powerful mob
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bosses. She would later say her
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relationship with Kennedy was a
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passionate romance and her connection to
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Gian Kana started as a friendship before
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turning intimate. She was walking a
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tight rope between two men who
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represented the opposite ends of
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American power. But this triangle wasn't
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just about sex. It was about politics.
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As the 1960 election got tighter, the
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Kennedy campaign grew desperate.
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According to several sources, including
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Sinatra's own daughter, Tina, Joe
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Kennedy asked Sinatra to get Gian
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Conor's help in securing the Union vote,
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especially in the crucial West Virginia
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primary and the battleground state of
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Illinois. An overwhelming and some say
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suspicious turnout for Kennedy in
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Chicago's Cook County ultimately helped
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him win Illinois by a tiny margin of
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just over 8,000 votes. Gian Car would
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later brag that Kennedy never would have
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been president without his help. And
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Judith Campbell was allegedly right in
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the middle of this unholy alliance. She
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later made the bombshell claim that she
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became an unwitting courier, a secret
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link between the president and the
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mobster. For about 18 months, she
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crisscrossed the country carrying sealed
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envelopes between Kennedy and Gian
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Carana. She claimed she arranged about
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10 meetings between the two men. The
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contents of those envelopes and the
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subject of those meetings are still
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debated by historians.
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Judith alleged the envelopes sometimes
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held cash payoffs from Kennedy to Gian
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Carana for his help rigging votes. Even
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more shocking, she claimed the messages
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were about a secret and dangerous plot,
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one where the CIA had hired Gian Car and
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other mobsters to assassinate Cuban
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leader Fidel Castro. The president of
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the United States was allegedly using
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his mistress as a go-between to talk to
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a mafia kingpin about election fraud and
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foreign assassinations.
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The scandal wasn't just a secret affair
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anymore. It was a matter of national
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security, a web of corruption
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threatening the very foundation of the
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Kennedy administration. Section five,
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the fallout. The Devil's Bargain, if
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that's what it was, wasn't built to
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last. Once in office, President Kennedy
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appointed his younger brother, Robert F.
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Kennedy, as attorney general. And Bobby
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Kennedy had one main goal, to wage an
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allout war on organized crime. For Sam
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Gian Connor, this was a stunning
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betrayal. He had allegedly put the
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president in power, expecting a little
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slack and some access in return.
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Instead, the full weight of the federal
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government, led by the president's own
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brother, was coming down on him and his
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FBI transcripts of secret recordings
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caught the mob's rage. Gian Kana felt he
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had been completely double crossed.
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Meanwhile, another powerful man in
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Washington was watching this whole
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dangerous situation with growing alarm.
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FBI director J. Edgar Hoover. The FBI
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had been watching Gianana for years and
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knew about his connection to Judith
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Campbell. When they found out she was
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also having an affair with the
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president, the alarm bells went off. The
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potential for blackmail was huge. In a
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private meeting, Hoover reportedly laid
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out the information for Kennedy, warning
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him of the catastrophic security risk.
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The message was clear. End it. Soon
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after, Kennedy abruptly cut off all
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contact with Judith Campbell. He also
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cut ties with Frank Sinatra. The break
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was so sharp that on his next trip to
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California, the president famously
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stayed at the home of Bing Crosby, a
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Republican, instead of with Sinatra, who
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had just built a helicopter pad at his
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home for presidential visits. For years,
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the story stayed buried. But in 1975,
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everything blew up. The Church
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Committee, a US Senate committee
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investigating abuses by intelligence
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agencies, started looking into the CIA's
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plots to assassinate Fidel Castro.
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During their investigation, they
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discovered the CIA had worked with the
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mob, specifically with guys like Sam
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Gian Carana, and they discovered a name
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that connected both worlds, Judith
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Campbell. Though the committee didn't
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release her name at first, it was
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eventually leaked to the press.
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Suddenly, Judith Campbell Exner, she had
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since remarried, was thrown into the
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national spotlight. The fallout was
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brutal. The press painted her as a mob
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mole and a call girl. Friends abandoned
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her. For her own safety, she became a
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recluse, terrified of payback from those
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who wanted to protect the Kennedy legacy
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or bury the mob's secrets. In 1977,
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trying to tell her side of things, she
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published her autobiography, My Story.
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In it, she confirmed her affair with
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Kennedy, but said it was purely
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personal. Years later though, as she was
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battling the cancer that would
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eventually take her life, her story
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changed. In a series of deathbed
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confessions, she revealed the darker
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details. Her role as a courier, the
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money, and the talks about the Castro
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plot. She even made the shocking claim
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that she'd had an abortion in 1962
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after becoming pregnant with Kennedy's
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child. The men at the center of the
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triangle met their own dark ends. On the
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night of June 19th, 1975,
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just days before he was supposed to
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testify before that same church
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committee, Sam Gianana was in the
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basement kitchen of his Illinois home.
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An unknown killer shot him once in the
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back of the head and then several more
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times around the mouth. A classic mob
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message for a man who talked too much.
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His murder is still unsolved. President
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Kennedy, of course, had been
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assassinated years earlier in 1963,
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an event that still fuels endless
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conspiracy theories, many of which point
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to an enraged and betrayed mafia looking
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for revenge. Conclusion: The story of
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Judith Exner, John F. Kennedy and Sam
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Gian Conor is so much more than a tale
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of a secret affair. It's a chilling look
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at the hidden places where power,
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politics, and crime all met in 20th
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century America. It reveals a world
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where the lines between the government
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and the underworld were terrifyingly
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thin, where the shiny image of Camelot
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might have been built on a corrupt deal
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with organized crime.
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The three main players, the president,
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the mob boss, and the starlet, each
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represented a piece of the American
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dream, twisted into a nightmare of
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secrets, betrayal, and death. Judith
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Exner spent the rest of her life defined
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by the powerful men she knew. She died
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taking whatever secrets she had left to
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her grave. The legacy of her story is a
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permanent stain on the romantic myth of
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the Kennedy years. A harsh reminder that
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history is often written in whispers and
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backroom deals. It leaves us with
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haunting unanswered questions. What was
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really in those envelopes she carried?
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How much did the mob really influence
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the 1960 election? And did this
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dangerous alliance ultimately play a
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role in the violence and tragedy that
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came later? It just goes to show that
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sometimes the most explosive secrets
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aren't kept in government vaults or
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gangster hideouts, but in the life of a
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single person caught in the crossfire.
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If you want to dive deeper into the
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hidden stories and forgotten scandals of
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history, make sure to subscribe and hit
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another investigation into the secrets