When you hear the name Joseph Kennedy, you might picture a savvy businessman and a political heavyweight. Yet, there are 10 terrible things that this patriarch pulled off, ranging from shady finance tricks to outright extremist sympathies. Below we unpack each shocking episode, giving you the full, unvarnished story behind the man who helped shape his son’s destiny.
10 terrible things Unveiled
10 He Made A Fortune Through Insider Trading
Joseph Kennedy was a prodigy when it came to making money. By the age of twenty‑five he already wore the badge of president of a bank – the youngest ever in the United States. While his hard work and sharp instincts certainly helped him amass wealth, the real boost came from a series of market maneuvers that would be illegal today.
He turned the stock exchange into his personal gold mine by employing tactics that modern regulators would brand as insider trading, creating artificial shortages to drive prices up, and short‑selling other equities to push them down. Back then those tricks weren’t outlawed, and Kennedy’s fortune ballooned as a result.
He knew exactly what he was doing. In a conversation with a classmate, Kennedy bragged, “It’s easy to make money in this market. We’d better get in before they pass a law against it.” Ironically, the very law that would later curb his methods was signed by none other than Kennedy himself. In 1934 President Franklin D. Roosevelt appointed him head of the Securities and Exchange Commission, quipping, “It takes a crook to catch a crook.” Kennedy then helped criminalize insider trading, effectively outlawing the very tactics that had built his empire.
9 He Brought His Mistress On Vacation With His Wife
Joseph Kennedy married Rose Fitzgerald in 1914, but the honeymoon quickly turned into a marathon of infidelities. A contemporary relative recalled, “Even in the early years of their marriage, Joe had a reputation for being a ladies’ man.” His most notorious liaison was with silent‑film star Gloria Swanson, who co‑starred in *Sunset Boulevard*. The two kept up a two‑year affair that was not always hidden from Rose.
The drama reached its zenith when Kennedy whisked both his wife and his lover away on a European vacation, forcing Rose to watch as he carried on with Swanson behind her back. Swanson later described Rose’s demeanor as stoic, noting that even if she suspected impropriety, “she never once gave any indication of it.”
Rose’s quiet endurance reflected the era’s expectations of women to endure silently. She and her children were fully aware of the affairs, yet a family secretary later recalled that Rose “never showed any pain” about the situation, embodying the belief that a woman’s place was to suffer in silence while preserving the family’s public image.
8 He May Have Been A Bootlegger
When Prohibition took hold in the United States, rumors swirled that Kennedy was quietly financing the illegal liquor trade. Allegations came from notorious gangsters such as Frank Costello and Meyer Lansky, both of whom accused him of bootlegging. Even a piano tuner employed by Al Capone claimed to have witnessed Kennedy in conversation with a whiskey magnate about illicit business.
While no definitive proof ever emerged, several concrete facts lend credence to the speculation. In 1922, Kennedy kept the party flowing at his Harvard twentieth‑year reunion, pouring liquor despite the nationwide ban. Moreover, when the 21st Amendment finally repealed Prohibition, Kennedy already possessed a sizable stockpile of alcohol ready for distribution across the country.
Kennedy always maintained that his supplies were obtained legally, suggesting that the bootlegging rumors might have been a smear campaign. Regardless of the truth, the episode illustrates his knack for spotting profit opportunities—legal or otherwise—and capitalizing on them with ruthless efficiency.
7 He Was A Vocal Anti‑Semite
In 1938, Joseph Kennedy accepted the post of American ambassador to the United Kingdom, a period that coincided with Adolf Hitler’s ascent and the intensifying persecution of Jews. Kennedy did not shy away from voicing his own anti‑Jewish prejudice. When news of attacks on German Jews reached him, he remarked, “They brought it on themselves.” He later added to a friend, “As a race they stink. Look what they did to Hollywood.”
His anti‑Semitic stance extended into diplomatic circles. He spent considerable time conferring with the German ambassador, Herbert von Dirksen, who later wrote that Kennedy “understood our Jewish policy completely.” Kennedy’s motivation was not humanitarian; he feared that excessive violence against Jews might turn global opinion against Hitler, jeopardizing his own geopolitical calculations.
Kennedy even tried to devise a scheme to relocate every German Jew to Africa or to a British/American colony, a plan that President Roosevelt promptly halted. Nevertheless, Kennedy’s public statements continued to echo support for Hitler’s policies, describing Jewish commentators as poised to “set a match to the fuse of the world.”
6 He Was A Nazi Sympathizer
Joseph Kennedy’s eldest son, Joseph Jr., attended a speech by Adolf Hitler in 1934 and came away impressed, writing that the German leader had identified a “common enemy” to rally the nation. He noted, “It was too bad that it had to be done to the Jews,” and added that “the dislike of the Jews, however, was well founded.” This sentiment mirrored his father’s own views.
Sharing his son’s admiration, Joseph Sr. advocated for a peace pact between the United States and Nazi Germany. While stationed in England, he worked to keep Winston Churchill out of office, hoping that Prime Minister Neville Chamberlain would forge an alliance with Hitler.
Kennedy even sought official permission to meet Hitler personally on two occasions, claiming his goal was “to bring about a better understanding between the United States and Germany.” President Roosevelt, however, blocked both attempts, refusing to allow a wealthy ambassador to negotiate with the Nazi regime.
5 He Said That Democracy Was Finished
Joseph Kennedy once told a reporter, “Democracy is finished in England. It may be here as well.” He believed the United Kingdom was merely fighting Germany to stay alive, not to combat fascism, and he applied the same logic to the United States. In conversations with von Dirksen, Kennedy claimed that President Roosevelt was a victim of “Jewish influence” and that the president would soon be ousted.
He went further, declaring that “the Democratic policy of the United States is a Jewish production.” Such statements were more than mere political commentary; they reflected a deep‑seated belief that Jews controlled American governance.
Roosevelt was outraged. Kennedy’s role as ambassador became untenable as he spread anti‑Semitic conspiracy theories and openly supported Hitler. In 1940, Roosevelt forced Kennedy to resign, effectively ending his diplomatic career.
4 He Lobotomized His Daughter
After his political ambitions were crushed, Joseph Kennedy turned his attention to grooming a son for the presidency. He saw his only daughter, Rosemary, as a potential liability. Rosemary displayed unpredictable behavior and frequent emotional outbursts, leading the family to label her as mentally handicapped—a diagnosis later questioned by modern psychiatrists who suspect she was merely depressed.
Desperate to “fix” the situation, Kennedy arranged a lobotomy for Rosemary. During the procedure, surgeons asked her to sing “God Bless America,” using her response to gauge how deep to cut. The operation stopped only when she became incoherent, leaving her severely impaired for the rest of her life.
Following the surgery, the family kept Rosemary’s condition hidden. Kennedy’s secretary recalled that “Rosemary’s name was never mentioned in the house.” The only evidence of her existence lay in a few family photographs tucked away in the attic.
3 He Supported Joseph McCarthy
When his son John F. Kennedy campaigned for the presidency, he publicly opposed Senator Joseph McCarthy’s infamous Un‑American Activities Committee. Behind the scenes, however, Joseph Sr. was one of McCarthy’s staunchest supporters. He donated generously to McCarthy’s campaign and leveraged his influence to secure a job for his son Robert on the committee, even arranging for McCarthy to become a godfather to Robert’s child.
This allegiance placed JFK in a precarious position. As public sentiment turned against McCarthy, Democrats moved to censure the senator. When a fellow senator knocked on JFK’s door asking him to sign a condemnation, Joseph Sr. erupted, shouting, “You’re trying to ruin Jack!”
JFK missed the actual censure vote due to a broken back, but he later recalled joking that if a reporter asked about his feelings toward McCarthy, he would “reach back for my back, yell ‘Oow,’ and pull the sheet over my head hoping to escape.”
2 He May Have Rigged An Election
In the 1946 congressional race, John F. Kennedy defeated his opponent, Joe Russo. Russo later alleged that Joseph Sr. orchestrated a vote‑splitting scheme by hiring a custodian who also happened to be named Joe Russo to run for the same seat, hoping voters would be confused and divide their support.
Rumors of electoral cheating resurfaced during JFK’s later presidential bids. When the younger Kennedy was preparing for the primaries, Joseph Sr. even approached Richard Nixon, saying, “Dick, if my boy can’t make it, I’m for you.” The elder Kennedy’s loyalty clearly lay with his family above all else.
JFK was aware of his father’s reputation, jokingly sharing a telegram that read, “Dear Jack, don’t buy a single vote more than is necessary. I’ll be damned if I’m going to pay for a landslide.” The anecdote underscores how Joseph Sr. kept a tight grip on political maneuvering, even if it meant bending the rules.
1 He And His Son Had Affairs With The Same Woman
“Dad told all the boys to get laid as often as possible,” John F. Kennedy once recalled, a mantra that would shape his own notorious reputation as a playboy. Joseph Sr. not only encouraged his children’s libertine habits but also boasted about them openly.
In 1940, a young JFK wrote to his father, bragging, “An awful lot of people were there, three girls to every man, so I did better than usual.” The ultimate testament to this family‑wide licentiousness came with Marlene Dietrich. She had an affair with Joseph Sr. in 1938, a liaison he flaunted in front of his son. Decades later, in 1963, JFK invited Dietrich to the White House, securing a private encounter with the sixty‑year‑old star.
Before departing, JFK asked Dietrich, “Did you ever get to bed with my old man?” Dietrich denied it, replying, “He tried, but I never did.” The exchange highlighted the father‑son rivalry and the lingering shadow of Joseph Sr.’s earlier conquest.