Hi, I’m Nat… and this is The Midnight Files.
Welcome to WTF Wednesday—where I find something mildly concerning…
and instead of moving on like a normal person,I research it for hours.
So… let’s unpack it together.
I was watching a Tv show called Love Story on Disney recently and
it follows the Love Story of John F Kennedy Jr and Carolyn Bassette you watch how they met, how their relationship unfolded,
and the pressure of constantly being in the public eye…
and how that slowly started to impact them.
and I’ll be honest…
I didn’t know much about the Kennedys before watching it.
I mean, I’m from Australia…
and it’s not exactly something we grow up learning about. I just kind of knew that JFK was assassinated when he was the president.
But I think you kind of know from the beginning
that this story isn’t going to end well.
Because let’s be honest—
I think most people don’t usually get a TV show made about them
unless something bad has happened to them
And for john and carolyns case… their story doesn’t have a happy ending either
John, Carolyn, and her sister were all on board this small plane that John piloting
and the crashes into the ocean and all three of them died on impact.
After watching their relationship unfold and somewhat getting to know who they were as people its sad knowing how it ends …Because yes I know its a TV show…
but it’s based on real life.
So after that, I was kind of fascinated with the Kennedy family and I started Googling them. And that’s when I realised john and caolyns death was just the scratching the surface
There are so many dark stories and events that follow their family
Multiple Plane crashes.
Assassinations.
Scandals.
Affairs. Secrets
Even a Lobotomy
It actually kind of reminded me of this show I watched on Netflix called The Fall of the House of Usher… where this family builds insane wealth and power, but not in the best way. and its built on greed, lies, cheating and it doesn’t end well for them. cause it all comes at a cost. And that cost is just… constant loss and misery.
The Kennedys were one of the most powerful and influential families of the 20th century.
And one point, it looked like they really had everything.
But a lot of their story is followed by tragedy.
So tonight…
we’re going to look into the Kennedy family—
how they rose to power…
and why their story feels less like history… and more like a series of unfortunate events.and yes that’s another movie reference…

The Kennedy story starts not in America…
but on the other side of the Atlantic ocean in Ireland.
The family descends from Irish immigrants Patrick Kennedy and Bridget Murphy who fled Ireland during the Great Potato Famine which started in 1845. Quick note about the potato famine—so basically… a disease wiped out most of the potatoes, and the food that was still fine was being sent out of Ireland to Britain. And in the end, millions of people either died… or had to leave.
So we can see why Patrick Kennedy and Bridget Murphy had to leave Ireland and they arrived in Boston Massachuettes in 1848 by boat, they arrived on these ships called Coffin ships. The reason why they were called coffin ships wasn’t because they were shaped like a coffin but because so many people died on board. I mean that would have been so grim to have to travel that journey on a boat like that…

The couple settled in Boston, where Patrick worked as a cooper which is a barrel maker and Bridget had on a variety of jobs over the years.
Something that comes up again and again in the Kennedy story… is that they were Irish Catholics.
And at the time, that actually mattered.
Because Boston was predominantly Protestant city… and because of that, they faced a lot of discrimination, had limited access to opportunities, and like many other Irish Catholic immigrants they were also poor.
Because, you know… history has never had a problem with judging people for what they believe in… ground breaking stuff …
Patrick and Bridget would go one to have five children: Mary, Johanna, John, Margaret, and Patrick but John dies at the age of 1 from cholrea which was quite common at the time.
But something that often gets overlooked in the Kennedy story… is Bridget.
When people talk about the earlier generations of Kennedy family, I feel like they tend to focus on Patrick, even later in 1963 JFK who was the American president at the time, when he visited his great-grandparents’ home in New Ross, Ireland. He spoke only about Patrick and his strong desire for liberty, his deep religious faith, the foundation he laid for the family’s future and being grateful for the inheritance.
But Patrick Kennedy died at a really young age of 35 and to put to put it in perspective Bridget and Patrick had only been in America for 10 years and married for 7 of them. He died from either consumption know to us as today tuberculosis or cholera I couldn’t find a definitive source to say which one as records at the time are not as they are today.
Bridget was left to look after 4 children on her own, in a foreign country and in a city that was mostly anti irish catholic environment..
At the time, Irish women like Bridget were often dismissed or looked down on—sometimes even called ‘Biddies,’ which was basically a term used for domestic servants.
She started out working as a maid… and later became a hairdresser in a Boston department store, before the Civil War..
She went on to become a successful entrepreneur owning a grocery store in East Boston, and investing in property, renting apartments most likely to other Irish immigrants.
And this is why I think she deserves way more credit.
Because she was a single parent, raising four children after losing her partner… in the 1800s, a time where that would have been incredibly difficult.
And somehow… she still managed to build something stable. Something successful.
She created the foundation that allowed her children to actually thrive.
And honestly… I don’t think women get enough credit for that.
So while history often remembers Patrick as the foundation of the Kennedy dynasty…
It was Bridget who actually held it together… and deserves the credit
One of Patricks and Bridget’s sons, Patrick Joseph Kennedy, would become the next step in the family’s rise to power.
Patrick was born in 1858, the same year his father died and he grew up watching his mother build a life from almost nothing.
And he didn’t waste the foundation his mother built… he actually did something with it.
Patrick J. Kennedy went on to marry Mary Hickey, who was also from an Irish immigrant family.
Together, they had four children—Joseph P. Kennedy Sr., Mary, Margaret, and Francis.
Patrick J. Kennedy became both a successful businessman and a Boston politician, building wealth through a network of bars and alcohol-related businesses which helped him gain local influence and connections. He knew how to tell people exactly what they wanted to hear… and used that to his advantage, running as a Democrat and being elected to the Massachusetts state legislature in 1884. He was the first Kennedy to hold public office and power. And honestly… I swear there’s something in the Kennedy genes—because they all seem to know exactly what to say… and people just eat it up.
And while he wasn’t the richest or most powerful Kennedy we’d ever see…
he was the one who opened the door.
Because from Patrick… came his son — Joseph P. Kennedy Sr.
The man who wouldn’t just build wealth…
He would turn the Kennedys into a household name… but it’s also a name now tied to so much tragedy
Joseph P. Kennedy Sr. was born in 1888 into a family that had already begun its rise to power. Because of his dad Patrick J kennedy he was surrounded by influence, ambition, and opportunity.
Joseph had big goals, and that started with university. And where else would he go other than a prestigious Ivy League school like Harvard?
Now, it was competitive… but not quite in the same way as it is today.
Because back then getting into Harvard, wasn’t just about your grades or extracurricular activities it was also about who you knew and who your family was.
And lucky for Joseph… he had a father with political influence, strong community connections, and money.
Which definitely didn’t hurt.
Because without that… it’s very likely his grades alone wouldn’t have been enough and he probably wouldn’t have been seen as the right ‘fit’ for the school
But even with those advantages, there were still limits. Because the Kennedys were Irish Catholic, and even into the early 20th century in America, they were still discriminated against and that meant exclusion from the most powerful social and financial circles.
So even though Joseph made it into Harvard… he was never fully accepted.
here were a lot of clubs at Harvard that Joseph would never be part of—not because he didn’t want to join, but because he simply wasn’t invited.
These weren’t the kind of clubs you could just sign up for. You had to be selected… and Joseph didn’t fit the mold.
At the time, Boston’s elite was dominated by what were known as WASPs—White Anglo-Saxon Protestants.
It wasn’t an official organisation… but it might as well have been.
They were the old-money, Protestant American elite—the ones who held social power, controlled opportunities, and decided who belonged… and who didn’t.
And if you were Irish Catholic, like Joseph Kennedy?
You were automatically on the outside looking in.
Which, when you really think about it…
is kind of wild.
Because it was a wealthy religous group of people who thought they were better than everyone else… and doesn’t that kind of go against the whole premise of their religion.
And it’s interesting… because he didn’t come from poverty.
But in those spaces, that didn’t really matter.
He was still judged for who he was.
But despite all of that… he kept his focus.
He studied, he made connections, and while he wasn’t a standout student, he did well enough—graduating in 1912 with a degree in economics
But graduating didn’t magically fix anything.
Those same barriers followed him straight into the real world.
Honestly… the guy couldn’t catch a break.
Gets into Harvard, still gets sidelined… and then steps out into the real world and it’s more of the same.
So naturally—
like any stressed 20-something with a very convenient safety net…
he went straight to his dad for help.
Through his father’s connections, he managed to get a job in banking
And to be fair—once he was in, he didn’t waste the opportunity.
He moved up quickly and by the time he was 25 years old, in 1914, he became one of the youngest bank presidents in the United States, taking over the Columbia Trust Company in Boston. Which, was not so coincidentally, as it was the only Irish-owned bank in Boston at the time.
So yes, he had help getting there.
But the bank itself wasn’t exactly thriving. It was struggling and at risk of being taken over… and he actually played a role in turning that around.
So while he didn’t exactly start from scratch…
he also wasn’t just handed a title and left to sit there. he had to prove he could actually do the job.
So now that joseph had the makings of succefsul career he started looking into other avenues of making money and gaining power and one of those was who he married.
Rose Fitzgerald was born in 1890. She was raised to be deeply religious and had a real love for music, especially the piano.
She wanted to study piano, history, and languages at Wellesley College where there was more academic freedom, critical thinking and independence. but her father, John F. Fitzgerald, said ah ahhh no daughter of mine will study as a Protestant school. You’re going to the convent…
So Instead, Rose was sent to the Convent of the Sacred Heart, and later to a convent boarding school in the Netherlands, called Blumenthal.
I felt kind of bad for Rose, cause Later in life, Rose said that not being able to attend Wellesley college was something she always felt sad about… but she also believed the religious training she received helped shape the foundation of her life. So basically, she made the best out a bad situation
It does make you wonder, though—where she might have ended up, or what she could have done, if she’d been able to make her own choices.
She clearly had a talent for music and a genuine interest in history and languages.
Sometimes I think we forget how lucky we are now—to have the freedom to choose our own paths. Because for us, the hardest part is figuring out what we want—not asking for permission to do it.
When Rose finished her studies she returned from the Netherlands back to boston, but she didn’t get to do whatever she wanted she now had to accompany her father to his political engagements, putting aside her own wants again.
So you can kind of see how her life was already preparing her for what was coming… a life as a politician’s wife, living constantly in the public eye.
She came from one of the most powerful political families in Boston. Her father, John Fitzgerald more commonly known as ‘Honey Fitz’, was the mayor of Boston at the time that Rose and Joseph met and began dating. Honey Fitz was known to be charismatic and deeply influential figure in Irish-American politics.
He served as the mayor of Boston twice, and during his time in office he worked on modernising infrastructure, improving public health, and trying to manage tensions between different social and ethnic groups.
Which, to be fair, was a big job there was a lot of social change in the early 1900s.
But at the same time… it wasn’t exactly groundbreaking.
His time in office was pretty standard for the era.
Before he was the mayor of Boston, he served in the U.S. House of Representatives and later returned to Congress in 1919
So Joseph and Rose met in Boston’s tight-knit Catholic social circles in the early 1900s. apparently they first met at Old Orchard Beach, when Rose was just seventeen.
But her father didn’t approve, as he felt she was far too young for anything serious.
So… what do you do when your father tells you to stay away from a boy…
You do it anyway and hide it…
The two of them began meeting in secret—rendezvousing behind the scenes, which was actually pretty controversial for the time, especially given how religious and traditional their world was.
Families like the Kennedys and Fitzgeralds were moving in the same circles… just not on the same level yet.
And Honey Fitz’s hesitation wasn’t just about Rose being too young—there was definitely more to it.
He didn’t think Joseph was good enough.
Or more accurately… he didn’t think he had the right social standing.
But Joseph really wanted the relationship to work. And as he started finding success in banking, things began to change.
Because it turns out, Honey Fitz didn’t just warm to Joseph…
he warmed to what Joseph could offer.
And with more money, more influence, and a clearer future ahead of him, Joseph started to look less like a risk… and more like someone who coudl elevate the Fitzgerald family even further
Joseph and Rose dated for several years before marrying in 1914, in what became more than just a union between two people…
it was a union between wealth and political power.
It’s hard not to wonder and question josephs motives.
was this really a love story—or a strategic move into one of Boston’s most powerful political families? Especially when you consider that Joseph courted rose for around 7 years and then would go on to have numerous affairs throughout his life while still being married to Rose.
In the 1920s, Joseph decided to go into a new venture the stock market, a world that, at the time, was largely unregulated. Insider trading wasn’t illegal, and market manipulation was common. Joseph understood how the system worked, and more importantly, how to use it to his advantage.
He made enormous profits during this period.
In the early 1920’s Joseph Sr joined the stock brokerage firm Hayden, Stone & Co., where he became an expert in the then-unregulated market... a system that, by today’s standards, would be considered not just unethical—but outright illegal.”
Then in 1924, Joseph Sr. was hired to protect the Yellow Cab Company from a ‘bear raid’— which is where investors deliberately try to drive a stock’s price down.
He successfully defended the company by manipulating the shares… but was later suspected of carrying out a bear raid himself to profit.
It feels like he’s not just building a fortune… but relying on increasingly shady
And somehow—very conveniently—Joseph got out of the stock market just before the stock market came crashing down… that caused that little event in history known as the freaking Great Depression.
By the end of 1929, he was sitting on an estimated $4 million. Around $75 million today.
Which is… impressive timing.
Suspiciously impressive.
But hey—maybe he was just incredibly lucky.
When the majority of America was struggling just to get by…
Joseph had cash and a lot of it
As property values collapsed across the United States, he began quietly buying creating a monopoly for himself.
Not small purchases… but major assets.
In 1933, he bought a mansion in Palm Beach for around $120,000—one of the Kennedy family’s most iconic homes.
And it just so happened to sit across the water from the very elite circles that had once shut him out.
Which feels… intentional.I see what youre doing their joseph
And he didn’t stop there. Through the late 1930s and early 1940s, Kennedy expanded into New York, acquiring commercial buildings at what were essentially “Depression prices.”
He was in a position to buy up property because he knew the market would recover—and he’d make money when it did.
And you can’t really blame him for that.
But at the same time… he was buying when most people had lost everything. People who didn’t have much of a choice but to sell.
So yeah, it was smart—but it also meant building wealth while others were struggling.
And when you add in things like insider trading and the timing of those real estate deals…
it starts to feel like he might’ve been picking up a bit of bad karma along the way.
One of his most strategic purchases was in 1943, when he purchased a prime property on 59th Street and Lexington Avenue in Manhattan for around $1.9 million, reportedly putting down only a fraction of that in cash if around 100,000.
He used leverage, borrowing heavily to control high-value assets, a strategy that allowed him to expand rapidly without tying up all his capital.
Then in 1945, he made what many consider his greatest deal.
He purchased the Merchandise Mart in Chicago for roughly $12 to $13 million, Kennedy used extreme leverage, reportedly putting down as little as $700,000 to $1 million in cash.
Just 15 years earlier, it had cost nearly double that to build the merchandise mart.
When Prohibition ended in 1933, Joseph P. Kennedy Sr. wasted no time at all.
He secured exclusive U.S. importation rights for several major British and international distillers through his company, called Somerset Importers Ltd.
Brands like Haig & Haig they sell Scotch whisky blends, Dewar’s Scotch, Gordon’s Dry Gin, and other European spirits brands
This was all legal as prohibition had ended but … it fuelled long-standing rumours that he may have already had connections in the alcohol trade during Prohibition and took part in the illegal distribution of alcohol.
There’s never been definitive proof of that but theres been a lot speculation
Joseph later sold Somerset Importers in 1946 for around $8 million—which would be well over $100 million today.
And even the name Somerset Importers may not have been a coincidence.
It most likely a pointed reference to the exclusive Somerset Club in Boston—a club that did not allow Irish Catholics like Joseph to join.
So it does show a more vindictive side to joseph and his quiet desires to prove something to those who once excluded him. Honestly cant blame him for that.
Joseph Kennedy’s wealth continued to grow through film, real estate, and strategic investments. He was involved in Hollywood, including the restructuring of RKO Pictures, and he invested heavily during the Great Depression, buying assets when prices were low and others were struggling. By the end of 1935 it was estimated that by short selling and reinventing in realest during the great depression, his fortune was around 180 million around 4.23 billion today. Which is just insane that he managed to get to that amount of wealth.
Now while Joseph was making big money… he was also making some pretty big decisions—mainly in the form of multiple affairs.
In the late 1920s, he moved to Hollywood… so he could be with his mistress Gloria Swanson—while still very much married to Rose, who was at home with their nine children.
And they weren’t exactly subtle about it either.
They were seen out together, openly acting like a couple.
And just to make things even easier… Gloria was also married.
At one point, her husband was conveniently sent off to Europe for work—which, unsurprisingly, made the whole situation a lot less complicated for them and made it even easier for them to walk around hand in hand like they weren’t married and in a normal relationship.
But Joseph didn’t just get involved in her personal life—he got involved in her career too.
He backed her film Queen Kelly, encouraged her to invest her own money into it, and positioned himself right in the middle of the production. Which, in theory, sounds great… except the film went wildly over budget, production fell apart, and it was never properly released in the U.S.
So now you’ve got a half-finished film, a lot of money gone… and Gloria’s reputation taking a hit.
Hollywood was already shifting from silent films to “talkies” at the time—which didn’t help—but this situation definitely didn’t do her any favours either.
And then… he was done.
He ended the relationship, went back to his wife, and carried on like nothing had happened.
Meanwhile, Gloria’s career had stalled—and her marriage didn’t survive it either.
So overall… it didn’t exactly end well for her.
Which, honestly… feels pretty on brand for Joseph at this point.
And that wasn’t even the only affair… he was linked to a number of others affairs over the years as well.
So Joseph’s back with the family on the estate, and instead of, I don’t know… reflecting on any of it—
he’s thinking, what next?
More power.
So naturally… he turns to politics.
He became a major supporter of Franklin D. Roosevelt’s presidential campaign, using his wealth and influence to back the future president.
And when Roosevelt won… Joseph was appointed the first chairman of the Securities and Exchange Commission in 1934.
Which is where it gets a bit ironic.
Because now—he’s the one helping introduce and enforce regulations to stop insider trading and market manipulation.
Under the Securities Exchange Act of 1934, the government brought in strict rules to clean up the stock market—cracking down on things like insider trading, where people used non-public information to make profits.
And Joseph Kennedy was right at the centre of it, helping bring structure and oversight to what had previously been a pretty unregulated system.
Which sounds great… until you remember he’s now making illegal the very tactics that made him rich
Now the way Joseph ran his home honestly isn’t that different to how he went after power, money, and politics.
He and Rose had nine kids—Joseph Jr., John, Rosemary, Kathleen, Eunice, Patricia, Robert, Jean, and Edward. Which already feels like a lot… but it wasn’t just a big family, it was a very intense one.
And I don’t even think they would’ve ever realised how unusual it was, because it was just normal to them.
Like yeah—most parents have expectations for their kids.
But this was that… on steroids.
There was a lot of pressure. A lot of discipline.
Everything was competitive, and very controlled. Joseph was dominant and strategic.
Rose was structured and deeply religious.
And their kids? They were expected to be good at everything—good grades, social life, politics… all of it.
Failing at something in that household would’ve been… kinda awkward.
Not really accepted—more of that “I’m not angry, just disappointed” vibe… but intense.
Even dinner wasn’t just dinner.There was no small talk. It was debates—politics, world events, the economy
There’s a scene in the TV series Love Story that actually shows this really well.
When Carolyn goes to the Kennedy house for dinner, she thinks it’s just going to be a normal family thing—chatting, getting to know everyone.
It’s not.
It turns into this full-on debate at the dinner table, led by Ethel Kennedy—firing questions about politics and economics, putting people on the spot, and everyone’s expected to just… keep up.
Carolyn clearly has no idea what’s going on—because John didn’t exactly warn her that this is what their dinners are like.
So she’s sitting there trying to follow along, feeling super uncomfortable, and the whole thing just makes her seem really out of place… when really, she just didn’t know what was going on
And Joseph? He was already incredibly successful by this point but his next goal was His eldest son Joseph Jr in the whtie house
Joseph Patrick Kennedy Junior was born on July 25, 1915.
From the moment he was born, his dad had big political plans for him,.
Because I swear these extroverted traits run in there genes, Joseph Jr was intelligent, confident, and naturally charismatic.
He also attended Harvard University like his father and was known for both his academic ability and his strong personality.
But unfortunately josephs political career would have to be put on hold because as World war 2 began and he willingly joined the united states navy.
He became a naval aviator and flew multiple missions.
By 1944, he had already completed a number of dangerous assignments.
But then he volunteered for something even more extreme.
A classified mission known as Operation Aphrodite.
The idea behind Operation Aphrodite was experimental and highly dangerous.
He was to pilot a Liberator bombers aircraft that would be filled with explosives. Sounds super safe
Pilots would take off, fly the plane to a certain altitude, and then bail out.
After that, the aircraft would be remotely controlled and directed toward German targets.
It was essentially an early form of a guided missile.
And it was incredibly unstable.
On August 12, 1944, Joseph Jr. took off from England in a plane packed with explosives.
Before he could bail out…
The aircraft exploded in mid-air.
The explosion was so powerful that it completely destroyed the plane.
And joseph jr was killed instantly.
He was 29 years old.
There was no warning.
No chance to escape.
No final moment.
Just an explosion in the sky.
The official explanation is that the explosion was caused by a technical malfunction.
As the equipment used in Operation Aphrodite was new, experimental, and known to quite unreliable.
That is the accepted historical fact.
But, as with many Kennedy tragedies, there have been theories and conspiracies and I do like looking into the other theories that people come up with. Because some fo them are just crazy
Some people have suggested the mission may have been sabotaged.
Others question why a mission that risky was given to someone seen as the family’s best shot at the presidency.
And then there’s the slightly darker conspiracy—whether Joseph Sr. and the family had already started shifting their hopes toward JFK instead of joseph and wanted joseph jr out of the way
That said, I don’t think anyone deserves to be put in that kind of danger, regardless of politics or family ambition.
And importantly, there is no credible evidence to support sabotage or these theories.
However, its undeniable that the facts are
Joseph Jr. was from one of Americas most ambitious political families and he was placed into one of the most dangerous experimental missions of the war. I wonder did he choose the mission willing or was he pressured into it but we’ll never know.

One year prior to Josephs death in 1943, something had already begun to shift from the focus on Joseph to his younger brother John F Kennedy who we know as JFK.
Joseph Jr has joined the US navy and so did his younger brother JFK,
JFK was serving the US navy in the pacidic duing world war 2.
He was in command of a patrol torpedo boat.
On the night of August 2nd, 1943… in the waters near the Solomon Islands…
his boat was struck and cut in half by Japanese destroyer called Amagiri.
Two of his crew died on Impact and the rest were thrown into the dark ocean… injured, disoriented… and miles from safety.
This next part of the story if what made JFK a war hero.
Over the next several days, he led his surviving crew through open water —
swimming between small islands, including Plum Pudding Island, and later Ola-sana Island.
At one point, Kennedy swam for hours, towing a badly injured crew member by a strap clenched between his teeth.
He continued to swim out into open water at night…
trying to signal passing Allied boats but wasn’t having any success.
He had to get creative and he managed to get Two local Solomon Islanders to pass on a coconut shell he with a message carved into to give to allied forces stationed near by on Nauru island. The allied forces were coastwatchers that may have been a mix of Australians and New Zealenders. So he was just kind of hoping that this message would get to them without being discovered by the wrong people. He carved this into the coconut
“NAURO ISL… COMMANDER… NATIVE KNOWS POS’IT… HE CAN PILOT… 11 ALIVE… NEED SMALL BOAT… KENNEDY.”
Days later… they were rescued.
The story spread quickly.
A young naval officer…
leading his men through survival, endurance, and determination.
It was the kind of story that builds a public image.
The kind that creates a hero.

So we’ve seen a pretty shady rise to power, cheating, and Joseph Jr. killed in a plane crash… And what follows after this starts to feel less like coincidence… and more like a never ending series of bad events Next week we will delve into even more craziness an assassination, more affairs, a lobotomy… and yes somehow, more plane crashes. I honestly don’t even know how one family ends up with that many plane crashes. And that’s today’s WTF Wednesday. Thak you for watching or listening how ever youve stumble across channel
Let me know what you think
I’ll see you in the next one for part 2.