On November 22, 1963, 24 year old Lee Harvey Oswald fired the shot that would change history. As crowds cheered on Dealey Plaza, the former Marine sharpshooter put a bullet through the head of America’s telegenic young President. It was the first successful assassination of a US president in 62 years. But Oswald didn’t live long enough to celebrate his grim achievement. Not two days later, Oswald would be dead too, killed by an assassin’s bullet while in police custody.
It’s a story you’ve doubtless heard many times before. But it’s also only a fragment, a single chapter in the vast, messy novel of Lee Harvey Oswald’s life. Born in 1939 to a New Orleans widow, Oswald was a man who tried his best to live a life of adventure. He enlisted in the Marines, defected to the Soviet Union, flirted with spies in Mexico City. But it was a single shot fired in Dallas that would cement his place in history. Join us today as we explore the life of America’s most notorious assassin.
When Lee Harvey Oswald first opened his eyes on October 18, 1939, he had no way of knowing he’d just been born into a world paralyzed by tragedy.
Not two months earlier, the boy’s father, Robert Oswald Snr., had died of a heart attack, leaving his heavily pregnant wife Marguerite to look after their two sons.
These dire circumstances may explain the dislocated early life baby Lee experienced.
In 1942, Marguerite sent Lee’s older brothers away to boarding schools. She tried to drop Lee at a local orphanage, but was told he was too young. Undeterred, she simply waited a year and then had him admitted.
And so began the incredibly depressing childhood of Lee Harvey Oswald.
For the next few years, young Lee bounced between orphanages, relatives’ homes, apartments Marguerite managed to briefly find and just as quickly lose… you name it.
In 1952, when the boy was 12, Marguerite even took him with her all the way across the country, as far from the bayous and old colonial piles of Louisiana as she could. All the way to New York City.
But if Ma Oswald was expecting the streets in the Bronx to be paved with gold, she soon got a dose of harsh, cold reality.
Life in New York City was hard. Marguerite took a job at a dress shop, but it required her to work backbreaking hours, hours in which her young son was left to his own devices.
As a consequence, Lee Harvey Oswald entered his teenage years lonely and rootless, spending long, listless days kicking his heels at the Bronx Zoo, or aimlessly riding the subway.
Technically, he was supposed to be in school, a fact that did not go unnoticed by the truant officer who picked him up one day in 1953.
By this point, 13-year old Lee had moved over 20 times in his short life, usually after Marguerite’s latest job or latest relationship blew up in her face.
The boy was surly, withdrawn. Prone to violence. He sometimes threatened others with a pocket knife.
So rather than just caution this wayward child, the truant officer sent him to a psychiatric facility.
There, Lee was found to suffer from neglect, but no actual mental illness. He was just another directionless kid with too much time on his hands and no-one to love him.
But while the love situation wouldn’t change, Lee’s life was about to get a whole lot of direction.
On June 19, 1953, Julius and Ethel Rosenberg were executed by electric chair at New York’s Sing Sing Prison for handing US secrets to the Soviets.
The execution galvanized New York’s leftists, who campaigned across the city in the weeks leading up, handing out leaflets.
One of these leaflets made its way into the hands of teenage Lee Harvey Oswald.
For the first time in his life, the boy encountered socialism. As the Rosenbergs’ bodies were quietly buried, Lee started reading books on socialist thought.
It was an obsession that survived even his next major move.
In 1954, Marguerite abandoned New York City, dragging her son back to New Orleans and an apartment on Exchange Alley in the French Quarter.
Today, the French Quarter is famous as a tourist hotspot. In 1954, though, Exchange Alley was the seediest part of a seedy city, crawling with pimps, prostitutes, and mobsters.
Lee even had a connection to the local mafia, via his uncle, Charles Murret.
It was a world Lee couldn’t wait to escape from.
In 1955, the teenager applied to the Marines, lying about his age, but was found out and rejected. A year later, aged 17, he tried again.
This time, he got in.
In 1956, Lee Harvey Oswald officially became a member of the United States Marine Corps. He likely hoped it would be the start of a new chapter in his life, a way to escape his problems.
But when your problems are as deep rooted as Lee Harvey Oswald’s were, escaping them is easier said than done.
So, here’s the thing about joining the Marines if what you really need is a place to settle and call home. That ain’t gonna happen.
No sooner was his training complete than Lee Harvey Oswald was shipped off to Japan, before being shipped off to the Philippines, and then back to the US.
Yep, it was his wayward childhood all over again. Only now the weapons he carried were bigger than just a pocket knife.
While in the Marines, Oswald managed to gain certification as a sharpshooter.
He also developed an interest in banned weapons, an interest that got him in a lot of trouble when his forbidden pistol accidentally discharged and wounded him.
The discovery of Oswald’s pistol led him to be court martialed, which led him to be court martialed again when he got angry and attacked the sergeant who was court martialing him.
The sorry debacle ended with Oswald spending time in the brig. When he emerged, he was more bitter than ever.
That’s not to say Oswald’s time in the Marines was all a disaster.
The young man continued to study Marxism, and learned Russian. He even began preaching about Marx’s ideas to his fellow Marines.
Note to any drill sergeants out there: if one of your marines suddenly starts being all pro-Soviet in the middle of the Cold War, it’s totally OK to tell the FBI, guys!
That goes double if you happen to be living in 1959.
On January 1 that year, Fidel Castro overthrew the Cuban government and installed the first Communist dictatorship in the Americas.
We don’t know precisely how Oswald reacted to this news. But we do know he intensified his efforts with his Russian.
By now, it was clear a plan was forming in the young marine’s mind. A plan that would help him escape his problems once and for all.
On September 11, 1959, Oswald got a hardship discharge from the Marines. Just nine days later, he boarded a boat to Europe, where he intended to apply to a Swiss college.
He never made it.
The moment Oswald reached England, he boarded a flight to Helsinki. There, he applied for and soon got a Russian tourist visa.
On October 16, 1959, Lee Harvey Oswald officially crossed into the Soviet Union.
Barely had the ink dried on his entry stamp then he declared to his Russian guide that he wanted to defect.
Thanks to spy movies, we tend to imagine the Soviet authorities were always on the lookout for Americans willing to go Red.
In reality, it didn’t quite work like that. Oswald wrote to the Kremlin, telling them he wanted to defect. The Kremlin took one look at his application and were all like “nahhhhh”.
The rejection hit Oswald hard. On October 21, the day his visa ran out, he slit one of his wrists in his hotel bathtub.
In hospital, Oswald was again interviewed by the KGB. Again, they decided he wasn’t defector material.
So Oswald forced their hands.
On October 31, the newly-discharged Oswald stormed into the US embassy in Moscow and declared he was going to surrender his citizenship. Worse, he was going to tell the Kremlin everything he knew about US radar codes.
In the minor storm that followed, the Kremlin reluctantly agreed to reopen his case. On January 4, 1960, they finally approved Oswald to defect to the Soviet Union.
When he got the news, Oswald must have felt like partying. Finally, it had happened. He’d found a way to escape his overbearing mother, to escape his wandering, American life.
Now he’d have a place in this world at last. A home to call his own. A home known as…
Belarus? Wait, what?
On a freezing cold January day, Lee Harvey Oswald was ordered away from glamorous Moscow to the grim, gray streets of the Belarusian capital, Minsk.
Rather than a fresh new start, the move would soon turn out to be a horrendous mistake.
A Lonely Exile
If you’ve never been to Minsk – and we mean it with all sincerity when we say “lucky you” – you should know it’s a city that will never win any tourist awards.
Rebuilt in a cold, Stalinist style following its total destruction in WWII, Minsk is Kiev without the charm, Chisinau without the nightlife, Warsaw without the edge.
Stepping off the train there in the dead of winter in 1960 must have felt only slightly less depressing than stepping off the Styx River into the Underworld.
Still, Oswald’s new life wasn’t without a certain charm.
Minsk in 1960 wasn’t a city that was used to seeing Americans. The moment Oswald arrived, he was treated as a celebrity.
Not only that, the Kremlin gave him a luxury apartment – luxury by USSR standards – and a plush job making radios.
With all this adulation, it was kind of easy for Oswald to forget what a precarious position he’d put himself in. Kind of easy to pretend his marine discharge being downgraded to “undesirable” might not cause him problems in the future.
It was only after about 6 months, when locals were used to him and the novelty of defection had worn off, that Oswald realized he was now living in a boring foreign city with nothing to do.
It probably didn’t help that the KGB was openly monitoring him. Oswald’s entire apartment was bugged, informants watched his every move.
By February, 1961, Oswald was writing in his dairy “(my) work is drab. The money I get has nowhere to be spent. As my Russian improves, I become increasingly conscious of just what sort of a society I live in.”
Barely a year after he first arrived in Minsk, Oswald began petitioning the US and USSR to let him return to America.
But the America that existed now was not the same one Oswald had left.
The previous November, a telegenic young man had narrowly squeaked home to victory in the US presidential election.
Known as John F Kennedy, he was the youngest elected president in American history.
Not that JFK preyed much on Oswald’s mind that year.
No sooner had he decided to leave Minsk than he found a reason to stay.
In mid-March, 1961, Oswald met Marina Prusakova by chance at a trade union dance.
Well, it was supposedly by chance. Marina’s uncle worked for Soviet intelligence, and it’s long been suspected he engineered Marina’s meeting with the American.
Regardless, the two hit it off and, a mere six weeks later, on April 30, 1961, they married.
Barely nine months later, on February 15, 1962, Marina Oswald gave birth to their daughter, June.
It was at this time that Lee Harvey Oswald began taking his return to the USA very seriously.
Aware that finding work in America with an undesirable discharge hanging over him would be difficult, Oswald came up with a desperate plan.
He wrote directly to Secretary of the Navy, John Connally, asking for his discharge to be scrubbed.
In return, he merely got a glossy leaflet asking him to support Connally for Governor of Texas.
It was more than just a slap in the face. To Oswald’s mind, it was like Connally had personally urinated on him and then seduced his mother.
From that moment on, Oswald began nursing a grudge against Connally that would soon grow to murderous proportions.
Undesirable discharge or not, though, the Oswald family’s petition to return to the USA was gaining steam.
It turned out Oswald never had surrendered his American citizenship, despite threatening to do so back in Moscow.
When this came to light, there was little the Americans or Soviets could realistically do to keep the family in Minsk.
On June 2, 1962, Oswald, Marina, and their baby daughter June all received permission to return to the US. They headed straight for Fort Worth, Texas, where they moved in with one of Oswald’s brothers.
Just like that, Oswald’s career as a professional defector was over.
He was now back in the land of the Free. And it wouldn’t be long before Oswald was using those freedoms to buy himself a gun.
Dreams of Cuba
So, given Oswald’s past, you’re probably expecting to hear how his return to America was marked by the Feds dragging him off for a lengthy interrogation.
Not quite. While the FBI did check in with Oswald, the CIA didn’t even bother to send anyone out to talk to him.
Unless you believe the theories that say the CIA did debrief Oswald, but then destroyed the evidence after JFK got shot to cover their tracks.
Either way, come summer, 1962, Oswald was living in Texas, looking for a job.
It was not a happy search.
Remember how we said his undesirable discharge might be a massive deal when looking for employment?
Well it turned out to absolutely be a massive deal. So many places turned Oswald down after learning about his unhappy break with the Marines.
According to people who knew him, Oswald responded to these setbacks by blaming the man who had refused to scrub his discharge: John Connally.
But not even an undesirably discharged defector is completely unemployable. In October, 1962, a Minsk émigré friend of Marina finally got Oswald a job in Dallas.
But there was something else that had caught Oswald’s magpie mind by this time: Cuba.
That fall, Oswald began to obsess over Castro’s new Cuba. He started to tell people Kennedy was a terrible president for authorizing the 1961 Bay of Pigs invasion – a bungled attempt to overthrow Castro.
It was at a Dallas party in February, 1963 that Oswald aired these views to one Volkmar Schmidt. Schmidt snorted and told Oswald he should be far more angry at Edwin Walker.
An ultrarightist, Walker had been forced to retire his post as a general for teaching his soldiers fascist ideas.
Something about Walker’s story caught Oswald’s imagination. He began to stalk the former general. Not long after, he ordered a pistol and a rifle through the mail.
On April 10, 1963, Marina was home late at night when Oswald came bursting through the door, white as a sheet, babbling that he’d shot him.
“Him” was Edwin Walker. Less than an hour earlier, a single bullet had come through Walker’s window, just missing the ex-general.
The shot had been fired by Oswald, who’d buried the rifle and fled the scene, convinced he’d killed Walker. It was only when Marina turned on the radio that Oswald realized he’d missed.
Not two weeks later, Oswald vanished from Texas.
This is where we get into the really mysterious part of Lee Harvey Oswald’s life.
We know he eventually resurfaced in New Orleans, but the timeline of what he did there is all confused.
Proponents of the theory that the mafia killed Kennedy believe Oswald spent his time in New Orleans getting connected to the mob via his uncle, Charles Murret.
Whether or not that’s the case, we do know he took a minor job at a coffee company, and sent for Marina and June to join him.
But all this was just a sideshow.
Oswald’s real interest in New Orleans was Cuba.
That May, 1963, Oswald founded a pro-Castro group, handing out leaflets in the street, trying – and failing – to recruit new members.
Yet he seems to have been playing some sort of game. In August, Oswald approached an anti-Castro group and offered his services. The group turned him away.
Still, Cuba remained a powerful draw in the young man’s mind. He appeared on local radio twice to defend the Castro regime. In September, he told Marina he was planning to hijack a plane and fly it to Havana.
Eventually, this strange dream completely consumed the dreamer.
On September 25, Oswald vanished from New Orleans, just as suddenly as he vanished from Dallas.
His exact movements that night are unknown. Years later, an anti-Castro activist in Dallas would recall a man named “Leon Oswald” showing up on his doorstep, asking for money to help the guerilla war against Castro. The activist refused.
Regardless, we know exactly where Oswald was by mid-morning the next day.
He was on a bus bound for Mexico City. And he had a plan that would make his past defection look like a mere warm-up act.
City of Spies
At the height of the Cold War, there was no more shadowy city in the Americas than Mexico City.
Officially, Mexico was neutral. Unofficially, it was a hotbed of clandestine meetings, dangerous games, and spies gunning to get the drop on one another.
Into this setup for a Graham Greene novel walked the most shadowy man of them all.
Lee Harvey Oswald arrived in the Mexican capital on September 27, after an all-night bus journey.
Barley had he dumped his bag in the hotel than he was making for the Cuban embassy.
Oswald had made up his mind. He was going to defect to Cuba.
OK, so remember how the USSR was initially all like “nah, dude, we don’t want you”? Well, Cuba was even more like “nahhhhh. Sorry, but nahhhhhh.”
Rebuffed, Oswald went to the Soviet embassy and tried to get a transit visa through Cuba, presumably hoping to defect when he landed. But the Soviets were also like “nahhhh.”
So Oswald went back to the Cubans. He literally begged them to take him. But they refused.
Broken, Oswald left the Cuban embassy. Five days later, he was on a bus back to Dallas, his shiny new dream in tatters.
At least, that’s the official version.
The unofficial version comes from reports by CIA assets in Mexico City when Oswald arrived.
They paint a very different picture.
The spy June Cobb reported Oswald had been spotted at a party attended by Cuban diplomats. While there, he was overheard joking about killing JFK.
Another asset claimed to have seen Oswald at a separate party, conversing with two Americans. These two men have never been identified.
Spooky stuff, eh?
Whether you believe the official or unofficial versions, there’s no denying that Oswald was back in Dallas by October 3. Exactly two weeks later, he took a job at the Texas School Book Depository.
From this point on, the story of Lee Harvey Oswald takes on a feeling of inevitability.
On October 20, Marina gave birth to Oswald’s second daughter. Just three days later, Oswald clandestinely attended a rightwing rally being held by Edwin Walker – the general he’d tried to shoot.
On November 1, the FBI came knocking at Marina’s door. She was living with a friend after a row with Oswald, and was surprised to discover the Feds wanted to talk with him. When word reached Oswald, he became jumpy.
On Tuesday, November 19, a local Dallas paper published the route the President’s motorcade would take through the city on Friday. Oswald noted that the car would pass right by his place of work.
He also noted that Governor John Connally would be riding alongside the president.
Finally, on November 21, Oswald went to the house of the friend Marina was staying with; incidentally, the same place he had left his rifle for safekeeping.
That evening, he tried to make up with Marina three times. Each time, Marina refused. Oswald wound up spending the night in the garage, his rifle beside him.
And that was how things stood as the clock ticked midnight and November 22, 1963 officially began. President Kennedy was on his way to Dallas, and Oswald was just a nobody who dreamed of being a somebody.
In just over twelve hours, that dream would become a nightmarish reality.
The Shot that Changed the World
The morning he entered the history books, Lee Harvey Oswald woke up early, removed his wedding ring, and left it and some money alongside the sleeping Marina.
He wrapped his rifle in paper, and took it with him to work on the sixth floor at the Texas School Book Depository.
At noon, Oswald’s fellow workers clocked off for lunch. He told them he would be right with them. Then he patiently waited until they’d all filed into the elevator and left, before going back to retrieve his rifle.
At 12:29pm exactly, as advertised, the presidential motorcade swung onto Dealey Plaza. As John F Kennedy waved at the crowds, the wife of Governor John Connally leaned toward the president and said:
“Mr President, you can’t say Dallas doesn’t love you.”
Those would be the last coherent words Kennedy would ever hear.
As the clock ticked over to 12:30, there was the distant crack of a gunshot.
If you watch the Kennedy footage carefully, you can see that Governor Connally heard this first shot. He reacts, starts to turn around…
And then the entire, sensible world shattered into a billion pieces.
There was another crack. A bullet went through the President’s throat, hit Governor Connally, causing him to slump forwards. In the car, Jackie Kennedy grabbed her husband, asking him what was wrong.
Up on the sixth floor of the Texas School Book Depository, Lee Harvey Oswald took aim with his rifle again.
Five seconds later came the third, final, crack. President Kennedy’s head jerked back with the force of the bullet. The screen faded to black.
The rest of that fateful afternoon you already know.
The images of panic in the streets are seared onto our minds. The sound of Walter Cronkite’s voice, disbelievingly telling the nation that President Kennedy is dead.
You know, too, the way Oswald fled the scene, only to shoot Officer J.D Tippit dead less than an hour later. You likely remember the story of how Oswald then tried to hide in a movie theater, only to be arrested shortly after.
At midnight that same day, Oswald was booked for assassinating the president and paraded before the press.
It’s only with hindsight that we can look at photos of that moment, and notice Jack Ruby, lurking in the background.
By the time the clock ticked over and November 22, 1963 receded into history, nobody on Earth had any doubt.
In less than 10 seconds that afternoon, a single man had pulled a trigger and changed the world.
The dream was over. Nothing would ever be the same again.
“I’m Happy that I got Him.”
After the drama of the previous day, Saturday November 23, 1963 was eerily quiet.
In Dallas, Lee Harvey Oswald sat in a police cell, protesting his innocence.
Outside, a local strip club owner named Jack Ruby hung around, asking every cop he saw what time Oswald would be transferred to another jail.
The only thing of note that really happened that day was the first broadcast of the long-running British sci-fi series Doctor Who. But we’re gonna guess maybe people in Dallas were too preoccupied to care much about that?
But if November 23 passed in stunned silence, November 24 would be marked by the crack of another gunshot.
At 11:17am that morning, Dallas police led Lee Harvey Oswald out into a waiting crowd to be transferred to another facility.
No-one noticed as Jack Ruby sauntered down the ramp towards the prisoner, murder in his eyes. No-one noticed the revolver being raised, the sudden movement.
There are photos you can find of the exact moment Oswald was shot. His mouth is wide open, his eyes bugging out his head. The crowd of policemen look blandly at him, as if they haven’t yet realized what is happening.
Oswald collapsed into a pool of blood. As he was grabbed by police, Jack Ruby was heard to shout:
“You guys couldn’t do it. I did it for you. I had to show that a Jew has guts. I’m happy that I got him.”
Less than two hours later, at 1:07pm, Lee Harvey Oswald was pronounced dead.
And that’s really the end of our story.
There’s simply no time here to go into the endless theories that grew in the wake of Oswald’s own assassination, linking him to the mafia, to the Cubans, to the Soviets, to the CIA. No time for the Warren Commission.
No time even to check back in with Jack Ruby, dying of cancer complications in his cell on January 3, 1967, remorseless to the end.
Perhaps the only thing we should mention is the little green book Secret Service agent Mike Howard found in Oswald’s apartment. The one with a kill list written in it and Governor Connally’s name decorated with daggers.
Of Kennedy’s name, there was no sign.
But even this is just a distraction from our main narrative.
There are plenty of videos on the JFK assassination out there, millions. If you want theories on who did what and why, they’re only a click away.
But our job today was to tell the story not of the conspiracy, but of the man at the heart of it. That job is now done.
Lee Harvey Oswald was laid to rest at Rose Hill Burial Park, Fort Worth, on November 25, 1963, the exact same day John F Kennedy was interred at Arlington Cemetery.
Finally, after 24 years of rootless searching, Oswald had at last found his home.
Excellent timeline of Oswald’s life: https://www.pbs.org/wgbh/frontline/article/twenty-four-years/
Timeline of the shooting: https://www.theguardian.com/world/2013/nov/22/jfk-assassination-timeline
John Connally theory: https://www.latimes.com/opinion/op-ed/la-oe-reston-jfk-assassination-target-20161122-story.html
Oswald in Mexico City: https://www.npr.org/2013/11/10/243981006/inconsistencies-haunt-official-record-of-kennedys-death
Oswald in the USSR: https://www.bbc.co.uk/programmes/w3cswsrd
June Cobb’s report: https://www.politico.com/magazine/story/2017/05/20/what-could-a-mysterious-us-spy-know-about-the-jfk-assassination-215143
Oswald’s defection letter: https://unredacted.com/2010/01/08/document-friday-oswalds-letter/