He Was A Problematic Patriarch
He dreamed of the White House—but left behind a curse instead. Joseph P. Kennedy Sr. was the powerful patriarch of America’s most iconic political dynasty, with presidential ambitions of his own. But behind the polished image lurked shady business deals, dangerous political sympathies, and scandalous affairs. In the end, his legacy wasn’t a presidency...it was a chilling trail of tragedy that would haunt the Kennedy name for generations.
1. He Was Born With Presidential Ambition
Joseph Patrick Kennedy Sr was born in September of 1888—and almost immediately began building a presidential legacy. His father, himself already a well-connected businessman and political figure, raised the younger Kennedy in East Boston. Before he graduated from Boston Latin School, Kennedy was already president (class president, that is).
But, of course, he had even higher hopes for the future, and more than enough fiery ambition to get there.
Wide World Photos, Wikimedia Commons
2. He Wasn’t Prestigious Enough For The Porcellian
With a stellar record and outsized ambition, Kennedy attended Harvard where he mingled with the other elites. However, his pedigree didn't get him everything he wanted. Perhaps it was Irish Catholic upbringing that kept him out of the uppermost echelons of the WASP-y Porcellian Club. Nevertheless, his peers saw him as “astute” with a keen "eye for value”. Soon, no one could deny his potential.
Emilio Kopaitic~commonswiki, Wikimedia Commons
3. He Was The Youngest (Bank) President
By age 25, after graduating from Harvard, Kennedy made his first big move towards the Oval Office. With a staggering $45,000 loan from friends and family, he staved off a hostile takeover of Columbia Trust Bank, an institution where his father held a considerable interest. In recognition of his actions, Columbia Trust made him bank president—the youngest in history!
The young buck was just getting warmed up.
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4. He Started A Dynasty
As the son of Patrick Joseph “PJ” Kennedy, Kennedy Sr already had political pedigree. But, when he married Rose Fitzgerald, the daughter of a Boston mayor, in 1914, he became a political powerhouse. Together, the pair formed an Irish Catholic dynasty that would forever reshape the face of American politics and power.
Though, not always for the best.
Photographer: Larry Gordon, Wikimedia Commons
5. He Profited From WWI
When the brutal, grinding fighting of WWI began ravaging Europe, Kennedy Sr was initially skeptical of any US involvement. However, that didn’t stop him from seeking to turn a profit. Kennedy Sr oversaw production of steel at the Bethlehem Steel shipyard where he caught the attention of a rising political star; one Franklin Delano Roosevelt.
Their friendship would prove pivotal.
Leon Perskie, Wikimedia Commons
6. He Treated Business Like A Battlefield
Kennedy Sr’s heartless money-making tactics continued after WWI ended. In 1919, he went to work for the Wall Street brokerage firm Hayden, Stone & Co, where he developed a reputation as a shrewd—if totally unprincipled—stock market trader. Suffice to say, he made the battlefield look positively civil in comparison. The battlefield, however, was about to come to him.
American Museum of Natural History, Wikimedia Commons
7. He Barely Survived
On September 16, 1920, Kennedy Sr’s dreams of a presidential future nearly came to an unceremonious end. As he was standing at the intersection of Wall Street and Broad Street, a horse-drawn wagon passing nearby exploded. The blast knocked Kennedy Sr off his feet—but he was one of the lucky ones. Several others perished in the unsolved attack.
When he stood up, he was even more ruthless than before.
Unknown authorUnknown author, Wikimedia Commons
8. He May Have Betrayed His Clients
In 1924, John D Hertz of the Yellow Cab Company brought on Kennedy Sr to help him stave off an attack from predatory short sellers. However, once the dust (or dollars) settled, Hertz had a sneaking suspicion that Kennedy Sr had orchestrated the bear raid himself, playing both sides of the market against a stock he was supposed to protect.
It wouldn’t have been the first time he got shady—or the last.
9. He Orchestrated A “Pump And Dump”
In 1933, Kennedy and some of his Wall Street associates pulled off another unscrupulous market manipulation. This time, they spread rumors that an auto-glass company had contracts to produce bottles as the Prohibition era came to a close. In reality, he and his friends had formed a “stock pool” to “pump and dump” shares based on the false news. He got away with it, of course, which probably explains why he eventually began to escalate...
Corporate author/original rights holder: FBO Pictures Corp., Wikimedia Commons
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10. He Saw The Crash Coming—Sorta
In his later years, Kennedy loved to claim that he had predicted the 1929 stock market crash that precipitated the Great Depression. He often told the story of selling all his stock after a shoe-shine boy gave him market tips. However, it’s likelier that the story came from Bernard Baruch. Historians generally agree that Kennedy escaped financial disaster “because he possessed a passion for facts, a complete lack of sentiment and a marvelous sense of timing”.
Either way, while people across the country fell apart, his own fortune positively soared.
National Archives Photo, Wikimedia Commons
11. He Turned Crisis Into Cash
While most Americans suffered through the Great Depression, Kennedy Sr only gained more and more. Between 1929 and 1935, his fortune ballooned from $4 million to a staggering $180 million (more than $4 billion today). He then used the money to set up trust funds for each of his nine children, guaranteeing they’d never have to work a day in their lives—however shortened they might be.
It wasn’t enough to be rich, however. He wanted to be liked as well.
Chinmaya S Padmanabha, Wikimedia Commons
12. He Took Over Tinseltown
By 1926, Kennedy Sr had conquered Wall Street on his way to the White House. As such, he set his sights on a new empire: Hollywood. He moved west and bought up controlling shares in hundreds of vaudeville theaters. Then, he merged his holdings to form RKO Pictures—one of the biggest studios of Hollywood’s Golden Age. But suffice to say, he wasn’t exactly in it for the art...
13. He Raided A Theater
Just because Kennedy Sr had left Wall Street, didn’t mean that he had abandoned his Wall Street business tactics. Shortly after arriving in Hollywood, Kennedy Sr went after Alexander Pantages’ chain of 63 profitable theaters. He made an offer of $8 million—a king’s ransom in the 1920s—but Pantages turned him down flat.
But if you haven't guessed by now, Kennedy Sr didn't like to take no for an answer.
14. He Played Hardball
After Pantages refused to sell his theaters, Kennedy Sr retaliated. He stopped distributing his RKO films to Pantages’ theaters, cutting him off from the industry pipeline and starving his screens of the movies that audiences most wanted to see. Still, however ruthless Kennedy Sr was, Pantages proved even more stubborn, still declining the sale.
That’s when things took a darker turn.
Frank Ross productions Ltd. Rko Radio Pictures, Wikimedia Commons
15. He Got What He Wanted—At A Bargain
Shortly after his standoff with Kennedy Sr, Pantages found himself on the receiving end of heinous allegations against a woman, Eunice Pringle. With his reputation destroyed and his fortune slipping away, Pentages saw that he had no choice: he sold his theater chain to Kennedy. By that time, Kennedy only had to pay $3.5 million for the beleaguered business.
The whole ordeal raised a serious question, though.
Los Angeles Times, Wikimedia Commons
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16. He Set The Whole Thing Up
Hollywood and business insiders all agreed: the accusations against Pantages were a little too convenient to be coincidence. Rumors swirled that Kennedy Sr had framed Pantages. The girl who accused Pantages even confessed in her final moments that Kennedy had put her up to it, orchestrating the entire plot to force Pantages to sell.
However, it may all have been an urban legend, depending on who's story you choose to believe...
Los Angeles Times, Wikimedia Commons
17. He Made Real Oscar Gold
Pringle’s daughter, Mary Worthington, later came forward to debunk the idea that Kennedy Sr had paid her mother to lie about Pantages. Regardless of the truth behind the rumors, however, Kennedy Sr made it out of Hollywood like a bandit. By the time he left Tinseltown, he had pocketed more than $5 million in profit—over $90 million today.
But, like many rich men of that time, it turns out money wasn’t all he got out of Hollywood.
18. He Had An Affair With A Movie Star
Hollywood wasn’t all business for Kennedy Sr—there was more than a fair share of pleasure. The married business magnate openly carried on an affair with the silver screen legend Gloria Swanson. Their affair was passionate, public—and profitable. He financed two of her films, though neither would become a hit. Their affair also ended just as controversially as it began.
Unknown authorUnknown author, Wikimedia Commons
19. He Didn’t Pay For Gifts
For a billionaire, Kennedy Sr turned out to be pretty cheap. Swanson thought that her billionaire businessman boyfriend was spoiling her with gifts…until she found the receipt. Kennedy Sr had charged the actress’ account for one of her own “gifts”. Needless to say, that ended the affair. But there was another reason that Swanson wanted out of the relationship.
Edward Thayer Monroe, Wikimedia Commons
20. He Was “Rough” And “Arduous”
In her memoir, Swanson spilled the tea on what it had been like to date, not just a Kennedy, but the Kennedy. And it wasn’t what it was chalked up to be. In the tell-all pages of her memoirs, she described Kennedy as a “rough” and “arduous” lover. Thankfully, it didn’t last long. She further wrote, “it was over with a hasty climax”.
Speaking of hasty…
Karl Struss, Wikimedia Commons
21. He Bankrolled FDR’s Big Break
In 1932, Kennedy Sr finally entered national politics. But it wasn’t for his own ambitions. Instead of entering the political ring himself, he threw his weight—and his money—behind FDR. It was his way into the inner circle. And as usual, the investment paid off. He wasn’t chasing power. He was buying it.
Unknown or not provided, Wikimedia Commons
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22. He Cashed In Before Anyone Else
After Hollywood, Kennedy Sr wasn’t done making money. While the rest of the country waited for Prohibition to end, Kennedy Sr was already securing import rights for major British hooch brands. With his good friend, FDR, just taking office, Kennedy Sr used his political connections to ensure he’d be first in line to profit from the changing laws.
This move gave rise to one of the most persistent rumors in American history.
23. He Was (Probably) Not A Bootlegger
Given his preemptive moves during Prohibition, rumors of Kennedy Sr’s “bootlegging” empire swirled—and have persisted for decades. However, historians have searched for evidence of Kennedy Sr’s questionable Prohibition practices and have come up empty. Biographer David Nasaw even called the rumors “just farcical”.
In fact, Kennedy Sr despised drinking—enough to make a pretty untraditional move in his personal life.
Unknown authorUnknown author, Wikimedia Commons
24. He Paid His Kids Not To Drink
Part of Kennedy Sr’s fortune may have come from the hooch business, but he didn’t sample his own product. In fact, Kennedy Sr was so opposed to the stereotype of the heavy-drinking Irishman that he offered each of his sons $1,000 if they stayed sober until age 21. Whether he ever drank or not himself, he certainly made a pretty coin on the white lightning.
25. He Bought The Biggest Building In America
Flush with cash from the Great Depression and the end of Prohibition, Kennedy Sr funneled his fortune into another business: real estate. And he went big! He purchased the Merchandise Mart in Chicago—the largest building in the world at the time. It wasn’t just a business move. It gave him influence, visibility, and power in a city that would become critical to his family’s political rise.
It was the biggest flex money could buy, and even so, just the beginning of even bigger money moves...
User:JeremyA, Wikimedia Commons
26. He Was In Charge Of Wall Street
After helping elect FDR, Kennedy Sr got a surprising thank-you gift: control of the entire US stock market. As the first chairman of the newly formed Securities and Exchange Commission, he was tasked with cleaning up the exact kinds of get-rich-quick schemes he had used to build his own fortune. He was surprisingly effective.
The original uploader was RMajouji at English Wikipedia., Wikimedia Commons
27. He Pretended To Be The People’s Champion
In a speech to the Boston Chamber of Commerce following his rise at the SEC, Kennedy Sr warned about the “frenzied financing of the late twenties”—despite, himself, having been one of the “frenziest” financiers. As head of the SEC, he promised protection for ordinary investors and gave Wall Street a much-needed facelift.
He was, indeed, a wolf in sheep’s clothing.
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28. He Got FDR Re-elected
When Roosevelt ran for reelection in 1936, Kennedy Sr was once again instrumental in getting the president across the finish line. He penned and published a book titled I'm for Roosevelt and made sure it landed on the desks of all of his business associates.
Quietly, behind the scenes, he was even more influential than anyone knew.
Franklin Delano Roosevelt Presidential Library, Wikimedia Commons
29. He Was The Church’s Favorite Capitalist
The radio priest Charles Coughlin had millions of devout Catholic listeners across America—but only one favorite businessman. In 1936, the increasingly popular priest heaped criticism on FDR and his policies, but, curiously, he had only good things to say about Kennedy Sr. He even called Kennedy the “shining star” of the FDR administration.
To Kennedy, it seemed God himself was priming him to replace his friend in the Oval.
Craine, Detroit, Wikimedia Commons
30. He Thought He’d Replace Roosevelt
When FDR appointed Kennedy Sr as ambassador to the UK in 1938, Kennedy Sr accepted the position with grace and gratitude. However, behind FDR’s back, he was plotting a hostile takeover. In 1939, he confidently told the British press that FDR would “fall” in the next election.
He wasn’t just predicting the future—he was planning a coup.
31. He Rubbed Shoulders With Royalty
As ambassador to the UK, Kennedy Sr lived like a king. He and his wife, Rose, quickly became darlings of British high society, dining with aristocrats and vacationing with royalty. The highlight? An opulent weekend at Windsor Castle hosted by none other than King George VI and Queen Elizabeth.
But he wasn’t exactly going to stick with the Brits when they needed him most.
Unknown authorUnknown author, Wikimedia Commons
32. He Ran From The Blitz
When the Third Reich started raining fire on London, Kennedy Sr didn’t stick around. Instead, he retreated with his family to the English countryside, far from the ruin and rubble. However, his cowardice didn’t go unnoticed. Winston Churchill’s son, Randolph, commented, “I thought my daffodils were yellow until I met Joe Kennedy”.
Things only got worse for him from there.
Cecil Beaton, Wikimedia Commons
33. He Tried To Make A Deal With The Devil
While Churchill called for resistance against aggression from The Third Reich, Kennedy Sr wasn’t quite as steely-spined. He supported appeasement and even tried—on multiple occasions—to secure a personal meeting with the dreaded fuhrer himself. He hoped that by meeting with the fuhrer, he might get “a better understanding” between the US and the totalitarian regime.
He was…not successful.
Official photographer, Wikimedia Commons
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34. He Thought Democracy Was Doomed
As the Third Reich’s forces swept across Europe, Kennedy Sr began making disturbing public statements. He openly advocated for American neutrality and downplayed the importance of Britain’s desperate struggle against evil. In a Boston Globe interview, he went so far as to say, “Democracy is finished in England. It may be here”.
Back home, his presidential dreams were unraveling fast.
35. He Was Defeatist
In yet another damning defeatist interview, Kennedy Sr told reporters that Britain wasn’t fighting for democracy—but for “self-preservation”. He said that, for the United States, helping the UK was simply a way for America to buy time. With statements like that, American voters weren’t sure if he was their UK ambassador, or a Third Reich spokesperson.
His allies began to distance themselves.
CNN, American Dynasties: The Kennedys (2018)
36. He Was Just A “Rich Man”
British politicians—once charmed by the flashy American millionaire—had turned on him. One MP sneered that Kennedy Sr was “a rich man, untrained in diplomacy, unlearned in history and politics, who is a great publicity seeker”. The MP further took aim at Kennedy Sr’s presidential ambitions, ridiculing his ambition to become the “first Catholic president of the US”.
What Kennedy Sr did next really ended his presidential potential.
CNN, American Dynasties: The Kennedys (2018)
37. He Said Something He Shouldn’t Have
Kennedy Sr’s comments went from being politically tone-deaf to outright appalling. According to Harvey Klemmer, his own staffer, Kennedy Sr once remarked that “[some] individual Jews are [all right][…]but as a race they stink”. Then he made things worse. Klemmer told Kennedy Sr what was happening to Jews in the Third Reich to which Kennedy Sr allegedly responded, “Well, they brought it on themselves”.
Then he buried his presidential hopes for good.
The Kennedys: A Fatal Ambition(2018), Channel 5 Television
38. He Sympathized With The Third Reich
In a private meeting with the Third Reich’s ambassador in London, Kennedy Sr made another shocking comment. According to diplomatic records, he said the Third Reich’s real mistake wasn’t persecuting Jews—it was being too loud about it. He reportedly added that he “fully understood” the Third Reich’s policies towards this particular minority.
All the while, his personal life was also in shambles.
CNN, American Dynasties: The Kennedys (2018)
39. He Vacationed With Marlene Dietrich
Before his fall from grace, Kennedy Sr took his family to the French Riviera in 1938. There, they stayed at the glamorous Hôtel du Cap—and quickly caught the attention of one particular guest: the iconic actress Marlene Dietrich. Despite the fact that Kennedy Sr was there with his family, he really only seemed to have eyes for Dietrich...
Twentieth Century Fox, Wikimedia Commons
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40. He Had An Affair With Dietrich
According to Dietrich, Kennedy Sr “followed [her] around” like a lovestruck teen at the glitzy hotel. Though she found him “sweet” she also noted that he was “old already”. Nevertheless, the two carried on a secret affair that would turn even more sordid when, decades later, Dietrich carried on a tryst with Kennedy Sr’s son, John—yes, that John.
Meanwhile, back on the political front, things looked disastrous.
George Grantham Bain Collection (Library of Congress), Wikimedia Commons
41. His Presidential Dreams Came Crashing Down
By 1939, Kennedy Sr had (not surprisingly) fallen out of favor with the FDR administration. While he was still technically ambassador to the UK, Roosevelt bypassed his old friend and began communicating directly with Churchill, leaving Kennedy Sr isolated and humiliated. By the end of 1940, Kennedy Sr had no choice: he had to resign in disgrace.
Just like that, his presidential ambitions were over. But there was still hope for the Kennedy name.
Unknown authorUnknown author, Wikimedia Commons
42. He Groomed His Sons For Power
By the time WWII broke out, Kennedy Sr’s presidential ambitions were long over—but his obsession with the White House wasn’t. He funneled his dreams into his eldest son, Joe Jr, hoping that his decorated son could fulfill the family ambition. But, when Joe Jr perished in combat, Kennedy Sr turned to another one of his children: John F Kennedy.
43. He Secretly Admired Nixon
Kennedy Sr’s political ambitions transcended party (and family) lines. Even though his son, JFK, would go on to become the hero of the Democratic party, Kennedy Sr’s only allegiance was to power. In 1960, he confessed to Richard Nixon—his son’s rival—that he admired his anti-Communist views. “If my boy can’t make it,” he told Nixon, “I’m for you”.
It wasn’t the first time he threw a child under the bus for power.
Oliver F. Atkins, Wikimedia Commons
44. He Thought His Daughter Was An Embarrassment
As his sons climbed the political ladder, Kennedy Sr turned his attention to a different kind of problem: his daughter, Rosemary. Her intellectual disability—and worsening behavior—concerned him. He worried she might ruin the family’s carefully manufactured image and derail his sons’ political careers before they could fulfill his ambitions and ascend to the White House.
So, he came up with a solution. A horrifying one.
Angus McBean, Wikimedia Commons
45. He Scrambled His Daughter’s Brain
Kennedy Sr consulted with doctors about how to deal with Rosemary and settled on a controversial procedure: a lobotomy. He believed it would calm her down and make her more “manageable” so that he could protect the family’s carefully crafted image. In 1941, surgeons cut into Rosemary’s brain. It would turn out to be the worst decision of his life.
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46. He Kept A Skeleton In His Closet
When the lobotomy failed catastrophically—leaving Rosemary unable to walk, speak, or care for herself—Kennedy Sr institutionalized her. But here’s the kicker: he didn’t tell anyone! Not his wife. Not his other children. And certainly, not the public. For the next twenty years, he kept Rosemary hidden away in a mental facility like a skeleton in his closet.
A skeleton he would never face.
47. He Never Visited His Daughter
After the botched lobotomy, Kennedy Sr heaped insult onto his daughter’s injury. Once she was in the mental facility, he never visited Rosemary—not once. As far as he was concerned, she was out of sight and out of mind. Author Kate Clifford Larson revealed that it wasn’t until Kennedy Sr suffered a debilitating stroke in 1961 that the rest of the family even learned where Rosemary was.
Even in his failing health, however, all he cared about was his legacy.
The Tragic Story of The 'Hidden Kennedy' (2021), Well, I Never
48. He Took The Secret To His Grave
It wasn’t until 1987—nearly two decades after Kennedy Sr’s demise—that the world learned the truth about what he had done to Rosemary. Until then, he had kept her condition a closely guarded family secret to protect his legacy. But his legacy was already cursed.
The Tragic Story of The 'Hidden Kennedy' (2021), Well, I Never
49. He Watched His Dynasty Collapse
In 1963, two years after suffering a stroke that left him debilitated, Kennedy Sr could only watch on in horror as his dreams fell apart. His son, JFK, fell to an assassin. Then, less than five years later, he lost another son, Robert, also to a crazed and brazen act. Incapacitated by his stroke, he could no longer express his grief through speech. His final public appearance came in a taped message with his wife and son, Ted.
The family legacy he built was already crumbling around him.
The Tragic Story of The 'Hidden Kennedy' (2021), Well, I Never
50. He Passed On A Broken Man
A year after Robert’s demise, Kennedy Sr passed on at his home in Hyannis Port. He was 81 years old. By then, he had outlived three of his four sons and institutionalized one of his daughters. The dynasty that he had tried so hard to build had already crumbled around him, tarnished by a curse that brought only scandal, tragedy, and loss.
The Tragic Story of The 'Hidden Kennedy' (2021), Well, I Never
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