10 Assassinations That Went Horribly Wrong

Keyword vibe check: This is a story about botched assassination plotsthe kind where a grand, grim plan collides with bad timing, worse logistics, and the universe’s favorite prank: “Oops.”

To be clear, nothing here is “funny” in the way tragedy is funny. But history is full of moments so absurdly miscalculated that the only sane responseafter the respectful pauseis to admit: humans are not as competent as our movie trailers suggest. These cases show how failed assassination attempts can hinge on a wrong turn, a jammed weapon, a heroic bystander, or a security detail moving like a well-trained swarm of bees.

And because this is a list-style deep dive, we’ll do two things for each entry: (1) tell you what happened (without getting graphic) and (2) explain exactly how it went wrongsometimes for the would-be assassin, sometimes for the target, and sometimes for everyone living on the same planet afterward.

1) The Assassination of Archduke Franz Ferdinand (1914): The “Wrong Turn” That Rewired the 20th Century

Some plots fail because the assassin panics. This one “succeeded” because the universe tripped over its own shoelaces and landed face-first into catastrophe.

In Sarajevo, a team of conspirators tried to kill Archduke Franz Ferdinand. Early attempts didn’t go smoothly: one attacker threw an explosive that failed to kill the Archduke, and the motorcade kept moving. By any normal standard, the plan had already entered its “abandon mission and pretend you were never here” phase.

Then the day made a hard left into dark comedy. A navigational mistake brought the Archduke’s car to a stop near one of the conspiratorsGavrilo Principcreating an accidental, point-blank opportunity. The result was fatal for the Archduke and his wife, and historically explosive for everyone else.

How it went horribly wrong

• Plan cohesion collapsed: an early failed attempt should have ended the operation.
• Chance beat strategy: a wrong turn and a stalled car turned “botched” into “deadly.”
• The aftermath dwarfed the act: the assassination helped ignite a chain reaction leading to World War I.

Why it still matters

This is the cautionary tale that proves a plot doesn’t need to be well-executed to be world-changingjust “lucky” in the worst possible way.

2) The Attempt on Andrew Jackson (1835): Two Pistols, Two Misfires, One Furious President

If you’re imagining a sleek, shadowy assassination attempt: nope. This one was public, chaotic, and ended with the target swinging a cane like he’d just been personally offended by physics.

Outside the U.S. Capitol, Richard Lawrence tried to shoot President Andrew Jackson. The first pistol misfired. Jacksonalready not famous for gentle conflict resolutionmoved toward him. Lawrence pulled a second pistol. That one misfired too. The crowd intervened, and Jackson survived what became the first known attempt on a sitting U.S. president.

How it went horribly wrong

• Reliability fail: both weapons misfired at close range.
• Immediate resistance: Jackson and bystanders reacted fast.
• Zero exit plan: the would-be assassin was quickly subdued.

Why it still matters

It highlights something security professionals know well: attackers often fail because they overestimate their control. Tools malfunction. People move. Crowds don’t behave like background extras.

3) Theodore Roosevelt (1912): The Bullet That Hit… a Speech

In 1912, Theodore Roosevelt was campaigning when he was shot in Milwaukee. The moment could have ended instantlyexcept the bullet had to pass through two oddly heroic objects: a steel eyeglass case and a thick, folded speech manuscript.

Roosevelt was wounded, but he didn’t immediately leave the stage. He delivered remarks anyway, famously framing the injury as proof that he was still in fighting shape. (This is the historical equivalent of texting “lol I’m fine” while actively not being fine.)

How it went horribly wrong

• Unexpected armor: the speech and eyeglass case slowed the bullet.
• Target behavior: Roosevelt’s decision to keep speaking reduced panicbut also ruined the attacker’s hoped-for “instant outcome.”
• Public control: the attacker was apprehended quickly.

Why it still matters

It’s a reminder that “small” detailswhat someone carries in their pocketcan reshape life-or-death outcomes. History is occasionally held together by stationery.

4) Franklin D. Roosevelt (1933): The Shot That Hit the Wrong People

Before FDR even took office, he survived an attack in Miami. The shooter fired multiple shots toward Roosevelt, but Roosevelt was not hit.

Instead, several bystanders were wounded, and Chicago Mayor Anton Cermak was struck and later died. Accounts highlight a key moment: a woman in the crowd reacted quickly and interfered with the shooter’s arm as the shots were firedan unplanned, split-second intervention that changed the outcome.

How it went horribly wrong

• A crowded environment: “aiming” in a dense public scene is chaotic, not cinematic.
• Bystander intervention: someone physically disrupted the attacker’s control.
• Collateral tragedy: innocent people paid the price for the attacker’s failure.

Why it still matters

It shows the grim truth of public political violence: even when the “target” survives, the event can still be lethaland historically consequential.

5) Harry Truman (1950): The Blair House Gunfight

While the White House was being renovated, President Harry Truman stayed at Blair House. Two attackers attempted to reach him there, leading to a violent confrontation with security.

Truman was not harmed, but the episode became infamous because it wasn’t a single quick shotit was a full-on, public security crisis, with a deadly exchange of gunfire and rapid containment.

How it went horribly wrong

• Security presence: armed protection created an immediate barrier.
• Time worked against the attackers: the longer it took, the more responders arrived.
• High visibility: the plot could not stay “quiet,” which is often fatal to a plan.

Why it still matters

It helped cement a modern reality: attempts on leaders can turn into wider public danger instantly, which is why protective details are designed to stop threats fasteven if that means chaos for a few minutes.

6) Charles de Gaulle (1962): The Car That Refused to Cooperate with Bullets

In the Paris suburb of Petit-Clamart, conspirators ambushed French President Charles de Gaulle’s vehicle. The attack was severehis car was hit repeatedlyyet de Gaulle and others in the vehicle survived.

Why? A cocktail of factors: timing, the driver’s reactions, and the plain mechanical fact that vehicles don’t always behave the way attackers expect. The attempt is remembered not only for its intensity, but for how it failed to achieve its intended result.

How it went horribly wrong

• Overconfidence: attackers assumed volume of fire would guarantee the outcome.
• Movement and split seconds: a moving target punishes bad coordination.
• Survival despite damage: “riddled” does not automatically mean “stopped.”

Why it still matters

It’s a case study in how real life rejects the math of certainty. Even well-planned violence can fail when the environment refuses to follow the script.

7) The July 20 Plot Against Hitler (1944): When “Close Enough” Wasn’t

One of history’s most famous assassination attempts involved a bomb intended to kill Adolf Hitler during a meeting. The conspirators’ plan hinged on proximity and conditions that would maximize the blast.

But the details didn’t line up the way they needed. The setting changed. The bomb’s placement shifted. The physics of the room did not cooperate. Hitler survived, and the failure triggered brutal reprisals against those involved.

How it went horribly wrong

• Environment change: room conditions reduced the blast’s lethality.
• Placement matters: small shifts in where the device ended up changed who absorbed the force.
• Aftermath disaster: the failed attempt led to a crackdown and executions of conspirators.

Why it still matters

It demonstrates the harshest “botched” outcome: not only failure, but catastrophic retaliationand a reminder that plots against entrenched power often pay a terrible price when they don’t succeed.

8) Gerald Ford (1975): Two Attempts in 17 Days, Both Undone by Small Mistakes

President Gerald Ford survived two assassination attempts in California within just 17 daysan eerie streak that reads like the plot of a tense miniseries no one asked for.

In Sacramento, Lynette “Squeaky” Fromme approached Ford with a gun, but the attempt failed because the weapon wasn’t ready to fire the way she expected. In San Francisco, Sara Jane Moore fired but missed, and a bystander intervened immediately, disrupting her ability to shoot again.

How it went horribly wrong

• Attempt one: a critical readiness failure (the moment required to make the gun fire never happened).
• Attempt two: aim + interruptiona miss and a fast tackle ended it.
• Human variables: Secret Service reactions and civilian courage broke the “plan.”

Why it still matters

These two events highlight a consistent theme: attackers often lose to “boring” realitiesmechanics, nerves, crowds, and someone nearby deciding, in half a heartbeat, to act.

9) Ronald Reagan (1981): The Shot That Bounced and the Seconds That Saved a Life

Outside a Washington hotel, President Ronald Reagan was shot and seriously wounded. Several other people were hit as well, including press secretary James Brady, who suffered devastating injuries.

What turned this from assassination into survival story was a brutal combination of quick protective movement, fast medical response, and the grim lottery of trajectory. Reagan later became known for responding with humoran attitude that helped calm the public and became part of the event’s cultural memory.

How it went horribly wrong

• Immediate protection: the protective detail moved Reagan into the vehicle quickly.
• Medical urgency: rapid treatment mattered.
• Unintended outcomes: others were harmed even as the main target survived.

Why it still matters

It’s a reminder that “successful” protection isn’t clean. A failed assassination attempt can still leave lifelong consequencesand change laws, public trust, and security practices.

10) George W. Bush (2005): The Grenade That Stayed Wrapped

In Tbilisi, Georgia, a live grenade was thrown toward President George W. Bush during a public appearance. It landed alarmingly closeclose enough to freeze your blood even reading about it.

But it did not explode. The reason is almost maddeningly simple: it remained tightly wrapped in cloth, which prevented the mechanism from functioning as intended. An alert security officer removed it quickly, and the crowdunaware of the full danger in the momentkept moving through history without realizing how near it had come to a different headline.

How it went horribly wrong

• Mechanical interference: the cloth wrapping prevented proper deployment of the grenade’s mechanism.
• Fast removal: quick action reduced risk to everyone nearby.
• Investigation follow-through: the case ultimately led to arrest and conviction.

Why it still matters

This one is a masterclass in unintended self-sabotage: the attacker tried to conceal the weaponand that concealment is what kept it from detonating.

Extra (About ): The Human “Experience” of a Botched Assassination Attempt

Lists like this can make history feel like a sequence of plot twists: misfire, wrong turn, heroic tackle, end credits. But the lived experience of an assassination attemptespecially one that failsis closer to a sudden tear in reality. People who survive these moments often describe the same strange rhythm: confusion first, certainty later.

In crowds, the initial sound can be misread. A pop becomes a balloon. A sharp crack becomes construction noise. There’s a brief, fragile window where everyone’s brain tries to keep the world normal because the alternative is too expensive to process. Then comes the second wave: people notice frantic motion, protective bodies moving fast, faces shifting into panic, and a collective realization that something terrible is happening right now.

For protective details, “experience” looks like training taking over. The goal isn’t bravery in the cinematic senseit’s choreography under stress. You’ll see the same priorities repeated across decades: move the principal, cover the angles, remove the threat, evacuate. In Ford’s case, a bystander’s split-second decision to grab an attacker’s arm shows that civilians can become part of that choreography, even without trainingsometimes at personal cost, sometimes at the cost of privacy, sometimes at the cost of being forever attached to a single moment.

Survivors also show wildly different reactions in the minutes afterward. Theodore Roosevelt kept speakingpart stubbornness, part showmanship, part refusal to give the attacker control over the narrative. Ronald Reagan leaned on humor later, which served a public purpose: it reassured people that the government still had a pulse. These reactions aren’t “right” or “wrong.” They’re coping strategies that also happen to become historical artifacts.

Then there are the bystanders and secondary victimsthe people history remembers as “also wounded” or “accidentally hit.” Their experience is often the most haunting because it has the least narrative protection. They didn’t sign up for the symbolism. They just stood in a crowd, went to work, or came to see a leader speak, and then their lives became footnotes to someone else’s headline. A failed assassination attempt can still be a life-altering tragedy for people who never had power, never had a motorcade, and never had the option to step behind bulletproof glass.

Finally, there’s the long-tail experience: security changes, public anxiety, and the way political violence echoes through everyday life. After an attempt, leaders often appear in public quicklynot because it’s easy, but because fear spreads when absence becomes the story. A botched assassination isn’t just a failed plan; it’s a stress test on institutions, on crowds, and on the human instinct to pretend tomorrow will be normal.

Conclusion

Across centuries, the pattern is uncomfortably consistent: assassination plots rarely unfold like clean, controlled operations. They unravel in the real worldwhere weapons misfire, drivers get lost, crowds interfere, and security reacts faster than anyone expects. Sometimes the target survives. Sometimes someone else doesn’t. And sometimes, as in Sarajevo, a “messy” moment becomes a hinge of global history.

If there’s a single lesson here, it’s that political violence doesn’t just threaten a personit threatens everyone nearby, plus the fragile social agreement that public life can be safe. And when a plot goes horribly wrong, it often leaves behind something worse than failure: collateral tragedy, tightened fear, and a historical scar that outlives the headlines.

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