Joseph Kennedy’s Path to the White House: The Mob’s Influence on JFK’s Election

41 Min Read

Joseph Patrick Kennedy Sr. made a few phone calls. He needed a favour. His son, John Fitzgerald Kennedy, wanted to become President of the United States. Victory was not exactly within his grasp, but Daddy, who had never relinquished control of his nine children, decided to take advantage of the underworld connections he had from the Prohibition era. He turned to mob leader Joseph Bonanno and made contact with Blue-Eyed Jimmy. He needed a connection to Sam Giancana, a mob boss in Illinois. There, the electorate had always voted for a Protestant candidate, the Kennedys were Catholics. Jack, as everyone called JFK, needed to win the US presidency in that state, and the similarly Protestant West Virginia would have come in handy too. Daddy decided to change the election result. He had the money, the power and the connections to achieve his goal.

In the end, he chose the singer Frank Sintara as his intermediary. He invited him to lunch. Sinatra assumed he wanted his voice, but Joe, as Joseph was called, enlightened him that he needed it for something much more important. “We know the same people. I know you know the people I mean.” Sinatra, an old acquaintance of the mobsters, knew. “We need the power of our friends in Chicago who control the unions. They can win elections for us. But, Frank, you understand I can’t go to them alone. It could come down to Jack. The White House should owe them nothing.” 

Sinatra understood. He played a round of golf with Sam Giancana. “My friend Jack Kennedy needs a little help in the West Virginia prelims …,” he reportedly began the conversation. Most of its inhabitants were Protestants. In May 1959, John F. Kennedy, a Catholic, defeated Hubert Humphrey, a Protestant, there, even though West Virginia had never elected a Catholic to a major office. Kennedy was not proven to have had any undue influence on the election result, but he was the talk of the town. 

West Virginia was only part of the deal Daddy Kennedy made with Giancana, but it wasn’t just the famous singer who was the link between the mob boss and one of the then 12 richest Americans who were not allowed to be seen together. It was also their shared mistress. Sinatra paid Judith Campbell $200 for her first night with the then 70-year-old Kennedy. The night turned into a “long and intimate relationship”, as Judith later recalled, which coincidentally became the mistress of Sam Giancana. 

He reportedly made sure that the young Kennedy won the election while he was meeting trade unionists and politicians all over America. “Votes were not so much bought as they were commanded, demanded and in some cases obtained by flattery,” the widow of one of the mobsters, Murray Humphrey, later recalled.

John F. Kennedy became the 35th US President by the skin of his teeth. His father was indifferent to the rumours of a rigged election and duplicate ballots, and was genuinely moved by his victory. He had once pinned his political hopes on his eldest son, Joe Junior. They collapsed when he exploded over the English Channel in 1944. Now his dreams have been realised by a cynical and distant Jack, whom he had not counted on. 

But the Mafia was counting on it. “All this will be repaid”, Giancana reportedly explained why he was so keen on Kennedy, but Kennedy forgot to return the favour. In the conspiracy theory, the Mafia thus became another possible assassin of the US President, while in the more real world, as soon as his son occupied the presidential chair, Daddy Kennedy thoroughly vetted his staff. President or not, Jack was his son and he wanted to keep control of him. He found himself an overseer who reported to him not only on what he was doing, but also on affairs of state. 

Cowboy in the Wild West

Joseph Patrick Kennedy was a surprisingly family man, though never a conventional husband. He cheated on his wealthy and powerful but devoutly pious wife Rose Fitzgerald, the eldest daughter of Boston’s first Irish-born mayor, almost from the day he met her. 

The regular delivery of the women, who were to him the equivalent of market goods, as one of his colleagues put it, was handled by his employees, and he was in charge of the money. The fair-haired descendant of Irish immigrants to America during the Great Irish Famine, when a million people died of starvation in Ireland between 1845 and 1852 and a million were forced to emigrate, he grew up in a fairly well-to-do family that sold alcohol for a living, but was far from wealthy. 

He graduated from Harvard with no financial problems, but his Irish background meant he was not accepted into the most select student clubs. It was then that he began to despise the business elite, even though he later became one of them. “The only thing these people understand is money”, he complained at the time, and later that everything should be taken away from them, “even their gold teeth”.

He bought a bus with a friend and started giving tours around the city. When he returned to his hometown of Boston, which he described as a pious city, the story repeated itself: the predominantly Protestant banks refused to hire him because they were afraid of the Irish. So he started his career in the field, but by the age of 25 he was already bragging that he was “the youngest bank manager in the world”. He was already closer to his goal: to be a millionaire by the age of 30.

Banking alone would not have got him there, but he was never that interested in work, believing only in money-making businesses, and in the 1920s he entered the car industry, Hollywood and Wall Street, which was then like the Wild West. He proved to be a great cowboy. He cleverly exploited the virtually unregulated trade, explaining that he needed to make as much ‘easy money’ as quickly as possible before the state would regulate the business. 

“I was worried that the stock market would close before I could buy everything I wanted,” he recalled of the time around 1915, when he was 27 years old and the stock market bubble was soaring skywards. Empowered by insider information, now illicit, and endowed with the ability to blackmail, flatter, seduce, manipulate and intimidate, he was a multi-millionaire by 1928, the year of his 40th birthday. 

In October 1929, the stock exchange was closed down. People committed suicide en masse. They lost everything they had. Joe rejoiced. When everyone from taxi drivers to shoe shiners had taken part in the stock market, he knew it was time to say goodbye. The value of the shares was over-inflated. 

He helped lift it himself. He teamed up with other businessmen and they bought each other’s shares to artificially boost their value. Even naïve Americans became interested in such shares. When they were interested enough, they sold them the shares at a high price. 

For example, he sold shares in Paramount Pictures at $35 per share. When the stock market crashed, he bought them back at $6 a share. Similarly, at the beginning of 1929, he got rid of all his risky investments and started again after the crash. 

Doctorate in tax avoidance

Before the stock market crash, his assets were worth around $4 million, and they were worth the same afterwards. Six years later, he had around $180 million under his thumb. Or, in today’s purchasing power, he turned his USD 57 million into more than USD 3.2 billion after the banking crash and during the Great Depression that began with it and left Americans dying of starvation. 

By the end of the 1950s, he was one of the 15 richest Americans, with a fortune worth between 200 and 400 million dollars then, or between 2 and 4 billion today. Thanks to his insider-boosted stock trading, the Kennedy family still owns around a billion dollars today.

After his death in 1969, the money could have been dissipated, but it could not. The ever calculating Joe introduced a safeguard: he distributed the money into trusts and stipulated that no beneficiary could reduce the principal by more than 10%. In this way, he protected the assets from incompetent heirs, but also from the tax authorities. 

Some of the estimated 33 funds today have only a few tens of thousands of dollars, some have as much as $25 million. Some 300 members of the Kennedy family are eligible. The wealthiest of them is Caroline Kennedy, daughter of John Fitzgerald Kennedy, but the estimate of her fortune varies widely: between $80 million and $500 million. The Kennedys like to say that they are a public family and their finances are private, so they just don’t talk about it, but it is estimated that Caroline receives between $12 and $30 million each year from trust funds.

The money in some funds is reportedly not taxed at all, another legacy of the skilful manipulator Joe, who was rumoured to check the tax burden first and then decide on the investment. But even though he also had a PhD in finding loopholes and exploiting all avenues to make money, including illegal ones, he was admired by his colleagues. 

He had an incredible amount of energy, with which he could work for unimaginably long periods of time. They were even more fascinated by his ability to “juggle numbers, accounts, people, employees and contracts as he flew from office to office, from city to city, from coast to coast”. His children never had to be involved in his business, and he opened a trust fund for each of them in his youth. But then, apart from him, hardly anyone knew what he was up to. 

Many details of his business and private life are still shrouded in fog, but it is clear that he did not, as is often said, smuggle alcohol during Prohibition, but he did make money out of it. Most of the family records are closed to the public, but those that are available show that he did a lot of business with the mobsters Frank Costello and Meyer Lansky. This does not prove that he smuggled alcohol, but it is very likely that he sold to the mob from the rich stock his father had before Prohibition.

The business was lucrative, but not as lucrative as the sale of alcohol immediately after Prohibition was lifted at the beginning of December 1933. As if by pure chance, Joe Kennedy went to England in November 1933 to secure the exclusive right to import and sell two of Britain’s finest brands of whisky and one of gin. And, again quite by chance, he set off with James Roosevelt, the eldest son of the newly elected US President. 

He had previously set up an import-export business at home, mapped out a sales network and rented warehouses. Now, under a law that allowed alcohol to be imported for medicinal purposes, he had shipped it to America, stashed it in warehouses and was waiting. When Prohibition was lifted not long afterwards, all he had to do was start selling it. 

Bookkeeper on a cloud of passion

He also turned his money around in Hollywood. “Look at these cleaners turning into millionaires in Hollywood. I could get them all the business,” he arrogantly proclaimed when he got there in his 20s. He bought an FBO film studio, started making low-budget films and learned public relations. He never forgot the lesson: he knew how to sell everything but himself to death. 

For example, he successfully persuaded the heads of film studios to come to Harvard, where he explained to them that they did not know how to make films, especially because they were constantly on the verge of bankruptcy, and that they needed a new way of production and distribution. After the lecture, he gave them a handbook with his name printed in gold letters on the cover. 

But soon after his arrival in Hollywood, one name was etched in his mind in golden letters: Gloria Swanson. She was the complete opposite of his pious wife, who believed that sex for pleasure was a sin and only allowed to conceive a child. As she had just given birth to her eighth child, her 38-year-old husband had time for a mistress whom everyone agreed was a lustful sex symbol. 

At the height of their relationship, he not only showed her around, he took her to Europe with him. Of course, his wife Rose, whom he married at the age of 26, was also on the trip. Until her death at the age of 105, she maintained that Gloria was just a poor girl who had been helped out of financial difficulties by her husband after she turned down a million-dollar contract to make independent but unprofitable films.

Although Swanson refused to allow photos to be taken together, everyone in Hollywood knew about the affair and even Rose’s father, another unfaithful husband, had reportedly heard about it. He reportedly threatened his son-in-law that he would tell his daughter about the affair if she did not break it off immediately, and she told him that she would divorce Rose and marry Gloria. The father-in-law fell silent. 

Rosa’s mother reportedly did not hold her tongue, but both the relationship and the marriage continued. It almost broke up in 1921, when Rose gave birth to her fifth child. She moved away temporarily, but returned and remained with her husband without disagreement until his death. In 55 years of marriage, she had got what she wanted: the status of a wife and a place in society. As long as this foundation was solid, she was not interested in other women. She had what she wanted: children, religion and money to shop. 

In her more than a century-long life, she has never spoken a single regrettable word about Gloria Swanson. Joe’s relationship with her failed because of them. Just two years after the affair began, Joe decided to boost Gloria’s fading film career by producing a high-budget film, Queen Kelly, starring her. Nothing went as it should have. 

He and Gloria got together and he drove to New York. At a press conference, he announced his retirement from the film industry. Gloria had to finish the film alone. She reviewed the business of her production company and froze in shock: Joe Kennedy hadn’t stopped counting on Cloud of Passion. He had dumped all the costs of Queen Kelly on her production company. She also bought her own gifts, which he gave her, invoicing her company for the fur products. Gloria was now not only alone, she was also penniless and careerless. 

A fox protects hens

But Joe, as always before, landed safely on solid ground. After making a fortune in the stock market and helping to crash it, President Franklin Delano Roosevelt made him Chairman of the Securities and Exchange Commission in 1934. Its task was to write laws to regulate the wild west of the stock market and help the country get back on its feet in the midst of the Great Depression. 

Washington roared: you can’t send a fox to guard the hens. Roosevelt didn’t trust Kennedy either, but he needed him. He knew the dirty business, so he felt he was the only one who could step on the toes of his own kind. And he did. 

Convinced that Roosevelt would not destroy capitalism, but save it, he was prepared to “happily bet half my fortune on the New Deal, if it means I get to keep the other half”. He persuaded businessmen to do business as usual, and he himself exploited every loophole he could find during his two years as chairman of the Commission.

Roosevelt was not blind. He too was clear that Kennedy was interested in nothing more than his private gains, and he refused to let him near the levers of power. He made a rich man with political ambitions chairman of the Maritime Commission, with the task of reviving American maritime trade. The Commission was marginal, Kennedy presented his work to the public as if he were saving the world. 

He often said that it’s not who you are, but how people see you. Now, image was more important to him than ever. Wealth no longer satisfied him, he wanted power. At the end of Roosevelt’s second term – he expected to be elected twice – he intended to become the new US President, the first Catholic to hold the office. 

He had to create an immaculate public image for himself before he could be nominated as the Democratic Party’s presidential candidate, and government departments seemed to have been commissioned to do just that. He lobbied hard, hobnobbed with Roosevelt’s son James even more eagerly than before, and in 1938 got the President to appoint him US Ambassador in London. The plan was the same as always: come, analyse, recommend, move on. He might have succeeded this time too, if Hitler had not interrupted his plans. 

It started off great. Kennedy was so cleverly woven into London’s social cream that not a day went by without a picture of him or a member of his family appearing in the newspapers. The three older children, Kathleen, Joe Jr and John, literally swept their British peers away with their American ease. 

Daddy Kennedy, of course, swept women first. His two sons, Joe, 23, and Jack, two years younger, knew by now that their 50-year-old father was their great rival, but they warned the girls at the embassy that he usually preyed on his prey at night. 

No one warned Prime Minister Neville Chemberlain about it, or he would not have listened, because they were of like mind: England must not stand up to Germany. When Hitler was already marching towards Czechoslovakia and war was at the door, Kennedy in London was bellowing loudly against it. He had no moral objections to it, in fact he had a moral attitude to a little thing, and he was bothered by the war because it was bad for business. 

So he tried to prevent it with a business strategy: bribe the Germans, give them what they want and peace will be peace. He conveyed to his President the assessment of Charles Lindbergh, an aviator who had been invited by the Germans to see their air fleet, that Germany was a European superpower in the air. He began publicly to convince the English that the Germans would defeat them in a matter of days. 

He and Prime Minister Chamberalin, who like him advocated reconciliation with Hitler, were also supposedly able to resolve the Jewish question: the German Jews would be relocated to Africa and elsewhere in Western Europe under British and American administration. The US President learned of his alleged plans from the newspapers. His ambassador forgot to tell him about them.

Kennedy’s anti-Semitism was well known from his days in Hollywood, which was then dominated by Jews. He liked to explain that a Jew here and there was quite all right, but that as a race they were losing. He also expressed his “complete understanding” of Germany’s problems with the Jewish problem to Von Dirksen, the German ambassador to England. 

Buried dreams

He went home for three months and told everyone that America had no place in this war. When he returned, London was a different place. A great opponent of the war, he boasted publicly of the influence he had on Prime Minister Chamberlain, and of the then relatively unimportant Winston Churcil, who had argued strongly against Hitler, he was fond of saying: “Never trust a man who is constantly hooked up to a bottle of whisky”. At other times, he warned people not to listen to this ‘drunken and warmongering’ fellow. 

Churchill did not strike back publicly, but rather ordered Kennedy to be followed, his phone calls tapped and his car routinely stopped and searched, claiming it was a matter of national security. The Kennedy dossier, as it was called, was getting thicker and thicker. It collected, among other things, rumours about Kennedy and what he said in private. 

So far, he has successfully got away with a lot. Of course, just because he became an ambassador, he had no intention of giving up his alcohol trade. When England entered the war in September 1939, for him it was “the end of the world, the end of everything”. Among other things, his whisky imports to America were threatened, but he quickly solved the problem: he shipped his precious cargo across the channel on government ships. Although they were overloaded, they had to find room for some 200 000 cases of the Ambassador’s whisky. 

He only curbed his abuse of power when a competitor threatened to launch a public debate in Congress on the improper functioning of the US Embassy in London. Of course, he found out about the threat from political friends before his competitors could act. 

Meanwhile, Churchill and the intelligence services tightened their net around him, until one of the US embassy officials got caught in it. In May 1940, it emerged that he had been leaking classified information to the Germans. Kennedy had to admit to his President that he was unable to ensure secure communications between them, and Churchill, the new Prime Minister, began to communicate directly with the US President. 

Thus, he first pushed Kennedy to the brink and soon took him off the political floor altogether. He successfully defeated America’s most powerful opponent of the war, a man who could have influenced the role America would play in the Second World War.

From then on, Kennedy often dined at home, according to those who followed his life. He also had no access to Churchill, who was almost at home with his predecessor. The cream of London excluded him and his family. 

Even the former Allies refused to listen to his constant repetitions about how the English were finished because the Germans were going to wipe her out. Lord Halifax, formerly himself an advocate of peace negotiations with Hitler, wrote in his diary: “Mr Kennedy is a most rotten specimen of a dupe and a loser. He is interested in nothing but his own pocket. I hope that this war will at least exterminate such men.”

When the German bombing of London began in the spring of 1940, Kennedy fled to the country with his mistress. He had already sent his family to America. Now those who had not given up on him before were turning away from him. From then on, Kennedy wanted only to go home. He pressed Roosevelt and finally got him to return to America in October 1940. 

On the way, he was on the verge of revealing to everyone how “that crooked bastard in the White House is dragging their children straight into the war”. He didn’t. He publicly backed Roosevelt, hoping that he would endear himself to the people again and win the presidency after all, only to have his hopes dashed by a statement he did not know would make headlines: ‘Democracy is over in Britain, and maybe it is over here’. Voters chose Franklin Delano Roosevelt to lead them a third time, and Joe Kennedy saw his dream come true in 1961 when his son became President.  

A man of great contradictions, he was, despite his relentless persecution of women, very much a family man. The Second World War did not spare him. In August 1944, a plane piloted by his eldest son, Joe Junior, exploded over the English Channel. He volunteered for service. His second-born son, Jack, was wounded over the Pacific Ocean. He felt the consequences for the rest of his life. His son-in-law Billy Hartington, the future Duke of Davenshire, was killed by a sniper in Belgium just four months after marrying Kennedy’s daughter Kathleen, better known as Kick. 

One rebellious and one missing daughter

Her marriage to Hartington nearly cost her mother a heart attack. It was so “horrible” that it “broke her heart”. What was so wrong with one of England’s most desirable bachelors, the rich and powerful Billy? He was a Protestant. Rose’s husband cheated on her regularly and even put himself in front of her with mistresses, but he was a Catholic. Billy was not saved by the fact that he was reserved and quiet and her daughter was rebellious and talkative. For Rose, a mixed marriage was like a hellish reunion.

She had almost given up on her daughter, even though Kick had been her life companion until then, because her husband was spending his time with other women. She did not come to her wedding. Only her eldest brother, Joe junior, was actually there. 

Fortunately for Mum, the marriage lasted only four months, and unfortunately for her, Kick decided to stay in London. She did not tell her parents about her new chosen husband, Earl Peter Wentworth Fitzwilliam. She did not expect that being a fabulously wealthy Protestant would make up for being married, drinking and gambling. 

She only told them the news after Peter had decided to divorce her. Now Joe was furious too. He often saw his mistresses as marketable commodities, and he was all the more vigilant about his daughter’s reputation. He had one of her early suitors checked to his underpants to see if he was good enough for her.

Now he was coming to Paris to talk to Kick and Peter about what to do. Two days before the meeting, the couple were on their way to Cannes. The plane landed in Paris to refuel. The pilot refused to take off because of turbulence, but Peter insisted. The plane crashed. All four people on board were killed. 

Instead of meeting his daughter, Joe identified her body. He attended her memorial service but did not go to her funeral. No one from her family was present when she was buried in England. The funeral was organised by her former mother-in-law. Yet Joe was broken. After the death of Joe junior four years earlier, there was no way he could recover. Now he was saying goodbye to Kick after Rosemary disappeared in 1941. 

He was responsible for her loss. The Kennedys’ eldest daughter was born in 1918 with mental health problems. She had stagnated at the level of a 10-year-old girl, except that in her teens she was no longer just a sweet little girl who was extremely loved by all the family members, even though she was not competitive like them; she was a rebellious teenager who knew how to escape from boarding school in the middle of the night. 

Joe decided to have her problem surgically corrected. At the age of 23, he had her lobotomised. He did not tell Rose about it, either before or after the procedure. Rose never wanted to talk about the “accident”, as she called the lobotomy, but she said that from then on her Rosemary was gone. Her personality had completely disappeared.

Love in the marital bedroom

But her father was the most resilient. At the age of 60, he had a new secretary, the attractive 24-year-old Des Rosiers, on whom every man’s eye, not just his, was fixed. He decided at first sight that she would be his, but first he hired her, then he rented a house for her ten minutes from his home in Palm Beach and visited her three months after he met her. He immediately started undressing her and kissing her. She was not surprised, then or since, when he started calling her house our home. 

“He taught me everything,” the secretary, who was a virgin until she met him, later recalled. In their nine years of relationship, she never knew his dark side, although she had heard about it. “He was funny, warm, attentive, never demanding, very perceptive and very gentle. It was not difficult to fall in love with him. He was utterly charming. I was completely taken by him.” They had sex, she reported, every day at least once a day.

They met wherever Joe was, because she was his personal secretary. When Rose was away, she had to move into the family home and share his double bed. Sometimes she moved in for a week or two. His children had no objections. They never knew the meaning of the word monogamy, so at least his sons never lived it. 

The house was full of staff, but even that meant nothing to Rosa. They loved Kennedy, but not his wife. She took advantage of them. Obsessed with appearances, she spent unbelievable sums on clothes, she went crazy with the staff if they got paid for a whole hour but worked for a minute less. For example, Des was annoyed when she bought more packs of tissues and toilet paper on a trip than Rose thought they needed.

Although she never said anything, Des was convinced that he knew about her relationship with her husband. What’s more, Des believed that Rose had got along with other women as long as she remained a common-law wife, but she still took tranquillisers for peace of mind. Her doctor prescribed five different kinds, plus four for her stomach, which was acting up, along with her nerves. 

She took her medication alone, with Des taking on all her other roles. His wife was not only in Kennedy’s bed, but also in his private life, managing the staff of his home, paying his salary, taking care of the family’s bills, accompanying him on his business trips, entertaining his guests, and so on. 

Well, sometimes there were three of them at a party, but otherwise Rose liked to walk around the house with a note pinned to her chest. She used it to write down what the staff needed to do, like fix a pillow in one room, throw away an old magazine in another, and so on. This was her main task when she was not in church or elsewhere. 

She and her husband were rarely at home together. She went shopping alone at least a few times a year in Paris, Vienna or Switzerland, spent a lot of time with her mother in Boston, and often stayed in the family home when her husband was away. 

They lived as friends with mutual respect, but without tenderness, almost without common interests. She hated sailing, he loved it, and he spent his days with Des on his new yacht, which he bought in 1952. She was in his home even when Mother, as Kennedy called his wife, was home. 

He never spoke to Des about his marriage and his relationship with his wife, although sometime in 1952, at the age of 68, he considered marrying her. Des resisted. She found their marriage comical, he was 36 years older than her. When his son’s presidential election campaign began, she was no longer by his side. At the age of 33, after nine years of marriage, she left him. 

She wanted her life, he, at 69, did not force her to share his. They parted amicably, and she remained in the same relationship with his children. During Kennedy’s presidential campaign, she was secretary and stewardess on Jack’s plane. She massaged his feet and hands, just as she once massaged his father’s temples and neck in his living room in front of his wife. 

But she did not want to be the President’s mistress. She accepted the post of one of his secretaries, but resigned after only a few weeks because of the working hours, which started at 8.30 and ended at 22.00. With no plans, she told the President that she wanted to spend a year in Paris. Would she be a secretary at the American Embassy in Paris? Would she. JFK picked up the phone. Des had a new job in five minutes. 

John spent only two years in his. In 1963, his father watched as he was murdered. Five years later, he saw it all again when his second son, presidential candidate Bobby, was shot. A good year after that, he himself died, having provided financially not only for his children, but also for future generations of Kennedys.

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