Why We’re Obsessed with JFK Conspiracies
Donald Trump says he’ll declassify all the files about the assassination. We’d never have got to this point if it weren’t for a weird ’90s film.
Today we're bringing you the third episode of Breaking History a new podcast in which I go back in time in order to make sense of the present.
The last episode was about the long history of progressives derailing California’s politics. In this episode, I explain how, exactly, the assassination of John F. Kennedy gave birth to so many wild conspiracy theories. If you want to understand why President Donald Trump recently ordered the director of national intelligence to plan how to release all the files relating to that dark day, you can listen to the episode below—or keep scrolling to read a print adaptation of it.
Every now and again, a work of art is so profound that it reaches into the real world and actually affects current events.
Consider, if you will, the most politically resonant piece of American pop culture produced in the last 50 years: the 1991 film JFK.
It was a full frontal attack on the American state: a three-hour video essay explaining just how and why the U.S. government, up to and including a former president, colluded to murder John F. Kennedy. It was explosive, including a long scene analyzing the famous Zapruder film—amateur footage of the assassination—meaning that audiences were forced to watch Kennedy’s head being blown off by a bullet again, and again, and again, and again.
JFK’s hero was played by the biggest movie star on earth, Kevin Costner, and given lines like: “President Kennedy was murdered by a conspiracy that was planned in advance at the highest levels of our government.”
And it was directed by the most celebrated filmmaker in America at the time, Oliver Stone—a dazzling Oscar winner, a traumatized Vietnam vet, a political firebrand, and a total crank.
The conspiracy he puts forth in JFK is vast. And yet, he was given $40 million to put it on the big screen. And the film wasn’t quashed by hidden political forces. No, it was nominated for eight Academy Awards, an insane endorsement of a wild accusation.
And JFK went on to change the course of history. There had always been Americans who believed that Lee Harvey Oswald hadn’t acted alone, or even shot Kennedy at all. But by the end of the Cold War, the conspiracy theorists were considered fringe and paranoid.
The release of JFK marked the moment conspiracy theories went overground, at the dawn of the internet age. Tinfoil hats were no longer just for oddballs, they were for moms and dads and me and you.
Stone had dressed JFK trutherism in Hollywood finery, and once the nation heard these accusations accompanied by a swirling John Williams score, the assassination was codified as a conspiracy in the minds of the American people.
You found it on Seinfeld; Jerry said: “I’m saying that the spit could not have come from behind. There had to have been a second spitter.”
And on The Sopranos; Tony said: “My cousin acted alone. I did not sanction this,” and Johnny Sack replied: “Lone gunman theory.”
You also found it in Congress. JFK was so significant that in 1992, just four months after its release, Stone gave testimony before the House. He hypothesized two interlocking conspiracies: first, about the role of the CIA and the Pentagon in the murder of JFK; and second, about a vast cover-up involving Lyndon B. Johnson, J. Edgar Hoover, and the Warren Commission, which investigated the assassination. In Stone’s mind, the twentieth century is a crime scene and the U.S. government is holding the murder weapon.
His testimony—and his film—were so influential that, in 1992, Congress passed a law ordering the government to release thousands of secret CIA files.
The question Stone asked is one that Americans still can’t get off their minds. And it seems, in 2025, like Trump is going to try to answer it. If this film about the deep state killing a president had never been made, we would not have arrived where we are today, with Trump ordering the declassification of the remaining files on the assassinations of JFK, Senator Robert F. Kennedy, and Martin Luther King Jr.
I can’t help but think of the eeriest quote from JFK: “We’re through the looking glass here, people. White is black, and black is white.”
Personally, I believe that it’s almost certain that Oswald acted alone. But at the same time, I can understand why people think otherwise. It isn’t as crazy as the conspiracy that the Earth is flat. The murder of John F. Kennedy is a really strange chapter of American history, full of mysteries, coincidences, and lies. And it’s a chapter in which the government squandered its most precious asset, the trust of the American people.
So, what happened on that day, November 22, 1963? What happened to send the nation down a rabbit hole it has never been able to climb out of?
First came the terrible news from Walter Cronkite, live on CBS: “From Dallas, Texas, the flash apparently official. President Kennedy died at 1 p.m.”
Next, Dallas police arrested Oswald, who, during his perp walk, both protested his innocence and revealed a curious detail about his life.
When a reporter asked: “Did you shoot the president?” Oswald responded: “No, they’ve taken me in because of the fact that I lived in the Soviet Union.
The Soviet Union? Wait, what?
Imagine what is going through the heads of the American people. How could a rational person not suspect that something sinister was going on?
And then, two days later, on live TV, Oswald was killed, depriving America of a trial. His murderer was a nightclub owner named Jack Ruby. When asked why he did it, Ruby’s motive didn’t seem solid. He did it, he claimed, because he just loved Jack Kennedy that damn much. He wanted to be a hero. But as the press dug into Ruby, it turned out that he was part of the Dallas underworld.
And so Ruby unlocked the first genre of JFK conspiracies: The mob did it.
The Mafia theory has largely faded in recent years, but it goes like this: The mob helped get Jack Kennedy elected in 1960, with the expectation that he would support the toppling of Fidel Castro’s regime in Cuba—which would mean the Mafia would get their Havana casinos back. But the new president refused to support an invasion of Cuba and appointed his brother Bobby Kennedy as attorney general. Bobby had been waging a vendetta against organized crime for years.
So the Mafia decided to kill the president.
I don’t buy it myself. There has been no evidence linking Oswald to the Mafia, and Gerald Posner, the author of the classic evaluation of the JFK assassination, Case Closed, has shown conclusively that Oswald fired the shot that killed the president.
But don’t worry, there are plenty of other conspiracy theories to choose from.
As the country reeled from Kennedy’s murder, more information came out about Oswald. He’s a very strange guy. A former Marine—he served for three years—Oswald was nicknamed Osvaldovich when he was stationed in Japan from 1957 to 1958, in part because he would talk incessantly about Marxism. An oddball with delusions of grandeur, at the end of his tour he began ordering Russian language newspapers to base.
After obtaining an early discharge on September 11, 1959 from the Marines, Oswald hopped a ship across the Atlantic and wound up in Helsinki, Finland. There, he walked up to the Soviet embassy, renounced his American citizenship and obtained a Soviet visa. When he arrived in Moscow on October 15, the KGB believed they had hit pay dirt. But within a few days, the Soviets realized Oswald knew nothing that could really help them—and told him they would not be granting him citizenship. Oswald was devastated; he went back to his hotel and slit his wrists. The KGB discovered him there and rushed him to a hospital.
After that, Oswald was sent to Minsk, now the capital of Belarus, where he was given a job in a radio factory. The KGB kept tabs on him. We know this because both Norman Mailer and later my Free Press colleague Peter Savodnik got access to reams of the KGB’s actual files. They include mundane details about Oswald’s eating habits, how often he masturbated, and what he discussed in the break room of the factory.
But while the Soviets knew everything about Oswald, when he was shot by Ruby in 1963, the CIA and the FBI claimed to know very little.
At the time of his death, Oswald was something of a political activist. He was a member of the Fair Play For Cuba Committee, a left-wing organization composed of many prominent intellectuals like Gore Vidal and James Baldwin. Oswald had become a spokesman for the group and even engaged in debates with anti-Castro émigrés. In a 1963 interview on a local television station in New Orleans, Oswald declared he was a Marxist.
Not a few months before he murdered Kennedy—having just tried and failed to kill a retired far-right general named Edwin Walker—Oswald took a trip to Mexico City and met with officials at the Cuban and Soviet embassies there, ostensibly to get a visa to travel to Cuba.
What the American authorities saw, in the man who’d just killed the president, was a communist defector to the Soviet Union who had returned to America and attacked its leader. Surely it was logical that he had been ordered to do so by the KGB?
It’s a fair question, and one that obsessed the leaders of our government. JFK’s successor, Johnson, was consumed by the idea that it could have been a Communist plot—and he was even more concerned by what that would mean for the future of planet Earth.
While recruiting people to serve on the Warren Commission, which was then being set to investigate the assassination, Johnson made it clear that he did not want anyone to blame the Cubans or the Russians.
For instance, on November 29, 1963, just a week after the assassination, Johnson called his former mentor, Senator Richard Russell of Georgia, and tried to cajole his old friend to serve. “We got to take this out of the arena where they’re testifying and [Nikita] Khrushchev and Castro did this and did that,” he said, “kicking us into a war that can kill 40 million Americans in an hour.”
Johnson asked Russell to join the commission to deflect attention away from the country’s enemy, the Soviet Union. He knows that the Cold War is on a knife edge and an accusation against the Soviets could tip into thermonuclear war.
This reminds me of Plato’s concept of the noble lie, when a leader has to practice deception in public for a greater good. But this noble lie would come to haunt America, because the deception helped undermine the American people’s trust in the story their leaders were feeding them.
Indeed, in his last televised interview, LBJ admitted to Cronkite that he could not bring himself to believe the official story. In 1975, two years after Johnson’s death, the full tape was revealed:
Lyndon B. Johnson: I can’t honestly say that I’ve ever been completely relieved of the fact that there might have been international connections.
Walter Cronkite: You mean you still feel that there might have been?
LBJ: Well, I have not completely discounted.
WC: That would seem to indicate that you don’t have full confidence in the Warren Commission report?
LBJ: I think the Warren Commission study, first of all, is composed of ablest, most judicious bipartisan men in this country. Second, I think they had only one objective, and that was the truth. And third, I think they were competent and did the best they could. But I don’t think that they, or me, or anyone else, is always absolutely sure of everything that might have motivated Oswald or others that could have been involved.
Absolutely wild! After years of being told to believe the Warren Commission Report’s assertion that Oswald acted alone, here was a former president of the United States suggesting that he never could “completely discount” that Oswald had been part of a great, unrevealed conspiracy.
This is why I approach anyone who doubts the official line on the assassination with humility and charity. They are not crazy; in fact, they are in illustrious company. Because here we have evidence that Kennedy’s own vice president—who many conspiracy theorists blame for a cover-up—entertains the idea of a conspiracy himself.
Back in the ’60s, inside the corridors of power, Johnson was not the only one doubting the official narrative. James Jesus Angleton, chief of the counterintelligence directorate of the CIA, also figured Oswald was engaged in a conspiracy with the Russians. He believed this even after a defector by the name of Yuri Nosenko told the CIA that the Soviets had nothing to do with it. Angleton was convinced that Nosenko was a double agent sent to America to feed him disinformation.
But with Stone’s JFK, conspiracy theories turned on America itself, pointing the finger at the deep state operating within the government. A seed was planted by former New Orleans district attorney Jim Garrison, who was the inspiration for the main character of Stone’s movie—the man played by Costner. The real-life Garrison openly declared his belief that the CIA was involved in Kennedy’s murder and linked the assassination to the government’s escalation of the war in Vietnam.
These views were catnip to the anti-war, anti-establishment Stone, who portrayed Garrison as the last Boy Scout, the brave soul willing to take on the American government.
Today, most JFK assassination researchers have dismissed Garrison as a charlatan. To buy into Garrison’s elaborate concoction, you have to start thinking of the world around you as an elaborate deception, where white is black and black is white.
For example, for Garrison, the fact that Oswald was a spokesman for a pro-Castro organization—the Fair Play for Cuba Committee—was actually evidence that he was deeply anti-Castro, like the CIA. His theory was that Oswald was actually a military intelligence agent, sent to Moscow, then allowed to return in order to build a credible backstory of Soviet involvement. It was the CIA who had organized the murder, said Garrison—and the CIA who made sure Oswald was perfectly placed to be blamed, and labeled a Soviet assassin.
The case made by the rogue district attorney, and partially co-signed by Stone, requires Oswald to play a part in something called Operation Mongoose—a very real, top secret CIA program, which, when you hear the details, sounds like an absurd fantasy.
Operation Mongoose dreamed up ways to kill and discredit Castro. One plot would place a chemical in his shoes that would cause his beard to fall out. Another was to booby trap a seashell. Exploding cigars? They pitched it. The Bugs Bunny ideas never really went anywhere, but they were part of a serious, broad campaign to eliminate Castro.
Why is it so implausible that this wacky bunch trained Oswald to kill Jack Kennedy? Well, the man who oversaw Operation Mongoose was unlikely to want JFK dead, given that he was JFK’s own brother: the attorney general, Bobby Kennedy.
Garrison remained a gadfly for years, but lived long enough to advise Stone on the film that revived his own reputation.
You could say the movie was an inside job.
Such was the power of Stone’s JFK that, in direct response to the film, Congress passed a law requiring the government to release the remaining files related to the assassination by 2017.
And, in 2017, Trump complied with that law—up to a point. But even the most unpredictable president drew a line at releasing them all.
Back in October 2024 though, Trump went on Joe Rogan’s podcast and explained that he would be opening the rest of the JFK files in his second presidency. And last month, he ordered the director of national intelligence to come up with a plan to do so.
Today, on the brink of a potentially monumental reveal of secret CIA files, can we expect any of these conspiracy theories to be validated?
For what it’s worth, Trump’s former CIA director, Mike Pompeo, does not think the coming declassification will shed much light on what we already know.
“The news value of them is grossly overrated,” he told TV presenter John Stossel. “I think we released—I can’t remember on our watch, 140,000, 180,000 pages of those documents while I was the CIA director.” And of the remaining documents, he said, “There’s less there than meets the eye.”
Author and journalist Jefferson Morley, who is among the most credible skeptics of the official narrative about the JFK assassination, told The Free Press he is hopeful there will be revelatory files in the release.
“Did the CIA find out that one guy killed the president for no reason and another guy came along and killed him for no reason? Or did they find out something else? Okay. The answers are overdue. Let’s just put it that way.“
Meanwhile, Posner, the author of Case Closed—the most persuasive book that Oswald alone killed Kennedy, is keen to find out everything the CIA and FBI knew about Oswald when he visited the Cuban and Soviet embassies in Mexico. “It’s not that there necessarily is a plot to kill the president, but maybe the CIA knew more about Oswald’s unhinged behavior at the Cuban and Soviet missions,” Posner told The Free Press.
“We had to have a lot of surveillance on those two enemy missions in the middle of the Cold War. And then what they should have done, of course, is share the information. When Oswald comes dejected back into the United States, 10 days later … an open investigation on that would have made the case a priority and potentially would have stopped the assassination.”
So, there is a chance that maybe, perhaps, we might discover some kind of conspiracy.
I welcome the sunshine. I want to know the remaining state secrets. But I also wonder if even this dramatic moment will ever satisfy the beautiful minds and the dot connectors. Because once you go through the looking glass, it’s hard to come back out.
If you believe in conspiracy theories, then why wouldn’t Trump and his allies be in on it, too? Or perhaps the documents proving who really had JFK murdered were destroyed long ago? You get the picture. When black is white and white is black, anything is possible and nothing is real.
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