Top 10 Historical Assassins Who Failed Spectacularly

History remembers the assassins who got it right—but what about the ones who flubbed it so badly they practically gift-wrapped their own arrests? This list isn’t about clean exits or clever escapes. It’s about the would-be killers who packed the wrong ammo, got distracted mid-murder, or just straight-up aimed like stormtroopers.

From guns that jammed to plots that unraveled faster than a toga in a wind tunnel, these are the top 10 assassins in history who gave it their absolute worst… and lived (briefly) to regret it.

Related: Ten Vicious & Violent Political Feuds from American History

10 Richard Lawrence vs. Andrew Jackson (1835)

Picture this: a soggy January morning in 1835, and Andrew Jackson, frail at 67 and attending a funeral at the Capitol, exits through the East Portico when Richard Lawrence—an unemployed painter who genuinely believed he was King Richard III—steps up and pulls a Derringer. He fires. Click—nothing. Panicked, he whips out a second pistol. Click—still nothing. Two perfect misfires in a row.

Jackson, livid, lunges at him with his cane and inflicts what one witness called “multiple wallops,” until passersby, including Congress member Davy Crockett, drag him off. The pistols were later tested and found to be in working order, suggesting rain-soaked powder was to blame.

Lawrence babbled about royal estates and was swiftly locked in an asylum for life. That day, Jackson became the first U.S. president to survive an assassination attempt—thanks to two guns and especially bad timing. The odds against both pistols failing? A mind-boggling 125,000-to-1.^[1]

9 John Flammang Schrank vs. Theodore Roosevelt (1912)

Imagine following a presidential campaign all the way to Milwaukee because you believe the dead president whispered in your ear to do it. That was John Flammang Schrank, convinced that McKinley’s ghost told him to stop Roosevelt’s push for a third term. He finally drew a .38 Colt revolver, aimed at Roosevelt’s chest—and fired! But the bullet had other plans.

First, it hit a 50‑page speech manuscript stuffed in TR’s pocket, then smashed into his steel eyeglass case. By the time it reached flesh? It barely nicked him. Roosevelt, bleeding but unbowed, dusted himself off, adjusted his sweater, and gave his speech anyway—quipping, “It takes more than that to kill a Bull Moose.”

Doctors later deemed the bullet too risky to remove, so Roosevelt carried it in his chest until his death. Schrank was declared insane and institutionalized for life.^[2]

8 Giuseppe Zangara Aimed at FDR, Hit Mayor Instead (1933)

Picture a sunny Miami scene: Giuseppe Zangara, a frail Italian immigrant armed with a .32 pistol, sneaks into a presidential viewpoint to take a shot at Franklin D. Roosevelt. He fires—misses Roosevelt entirely. One bullet ricochets off a metal pie tin and strikes Chicago Mayor Anton Cermak, who later dies of peritonitis worsened by the wound.

Zangara is tackled and arrested on the spot. He confessed he didn’t hate Cermak—he “just wanted to kill the big guy.” He also declared, “I have the gun in my hand. I kill kings and presidents first and next all capitalists.”

Zangara, who suffered chronic pain and blamed world leaders for his misery, was executed in Florida just weeks later. A presidential attempt turned into a tragic case of wrong place, wrong mayor.^[3]

7 Oscar Collazo & Griselio Torresola vs. Harry S. Truman (1950)

Meet the ultimate duo of dysfunction: Oscar Collazo and Griselio Torresola, two Puerto Rican nationalists determined to assassinate President Truman at Blair House. The problem is, they had zero intel and zero planning. Collazo’s pistol failed to fire at first because he hadn’t chambered a round—oops. Torresola was more lethal, killing officer Leslie Coffelt, who—despite being mortally wounded—returned fire and killed Torresola.

The shootout lasted less than a minute. Truman, awakened mid-nap, peeked out the window as chaos erupted. Later, he deadpanned: “A president has to expect these things.” Collazo was sentenced to death, but Truman commuted the sentence to life—he was eventually released by Jimmy Carter in 1979.

The Secret Service rewrote its protocols afterward. A botched plot with bloody consequences and one heroic final shot.^[4]

6 Vladimir Arutyunian vs. George W. Bush (2005)

In 2005, Georgian President Mikheil Saakashvili was hosting U.S. President George W. Bush in Tbilisi’s Freedom Square. Enter Vladimir Arutyunian: 27, angry, and packing a Soviet-made RGD-5 hand grenade. From just 82 feet (25 meters) away, he lobbed the thing—wrapped in a red handkerchief—straight into the crowd near the podium.

No explosion. No panic. Nothing.

Secret Service agents discovered the grenade later, still armed but inert. Why? Arutyunian had wrapped it too tightly, jamming the safety lever and preventing detonation. Bush was unaware of the incident until hours later.

After fleeing, Arutyunian killed a Georgian agent during a standoff but was wounded and captured. He confessed fully and is now serving a life sentence. Moral: if you’re going to throw a grenade, don’t gift-wrap it.^[5]

5 Lynette “Squeaky” Fromme vs. Gerald Ford (1975)

Squeaky Fromme, a fervent Charles Manson follower, stalked President Gerald Ford in Sacramento, California, in September 1975. She approached him in a crowd, brandished a Colt .45 pistol—and forgot to chamber a round. The trigger was pulled, but no discharge. Ford was escorted away calmly.

Fromme stood still and was tackled by Secret Service agent Larry Buendorf, who disarmed her within seconds. She later claimed she only meant to frighten the president into addressing environmental issues, especially redwood preservation. Her “message” was more eco than execution.

Sentenced to life in prison, she served nearly 35 years before her release in 2009. A weapon that never fired. A protest that landed her behind bars.

Remarkably, just 17 days later, Ford survived a second assassination attempt—this time in San Francisco, where Sara Jane Moore fired a revolver at him from across the street. Her shot missed, and she, too, was quickly subdued. Ford became the only U.S. president to survive two assassination attempts in the same month.^[6]

4 Felice Orsini vs. Napoleon III (1858)

Paris, January 14, 1858—Felice Orsini, a fiery Italian revolutionary, hurls three homemade bombs at Napoleon III’s carriage, hoping the blast will spark Italian independence. Instead, the only sparks fly from panicked horses. Eight bystanders die, 140 are wounded—including a policeman. Orsini is knocked senseless, staggers home, and is arrested the next morning.

None of the bombs harmed Napoleon III or Empress Eugénie. From prison, Orsini wrote a passionate letter urging the emperor to support Italy’s liberation. He was guillotined seven weeks later. Though a failure in execution, the attack influenced public sentiment and indirectly contributed to Italian unification. Call it a deadly case of misguided idealism—and premature detonation.^[7]

3 Max Hödel vs. Kaiser Wilhelm I (1878)

At 3:30 p.m. on May 11, 1878, Berlin plumber-turned-anarchist Max Hödel sneaks up on Emperor Wilhelm I and his daughter as they ride past in an open carriage along Unter den Linden. Hödel fires two revolver shots—both miss. He runs across the street and fires again—still no hit.

However, a bystander is mortally injured. Hödel is tackled and arrested immediately. Expelled from the Socialist Workers’ Party just weeks earlier, Hödel acted alone, but Bismarck used the event to justify sweeping Anti‑Socialist Laws.

Hödel was tried for treason and executed that August. What should have been a royal assassination became political propaganda—built on a bad aim and cobblestone chaos.^[8]

2 George McMahon vs. King Edward VIII (1936)

Imagine the proud Trooping the Colour parade in London, July 16, 1936. King Edward VIII rides by on horseback, every eye on him—when suddenly, a scruffy man in a brown suit (George McMahon) pulls a revolver. It falls to the ground during a scuffle, landing beneath the king’s horse. Edward tips his hat and rides on, unbothered.

McMahon later claimed he was hired by foreign agents but botched the job to expose a conspiracy. MI5 had allegedly been aware of him and may have supplied the gun, though theories remain murky. Another man was arrested nearby with a weapon, adding to suspicions.

McMahon was sentenced to 12 months’ hard labor. No shots fired, no royal harm—just a tangle of secrets and missed opportunities.^[9]

1 Operation Valkyrie Conspirators vs. Adolf Hitler (1944)

Picture it: a cozy briefing room at Hitler’s Eastern Front HQ. Colonel Claus von Stauffenberg places a suitcase bomb under a sturdy oak table. Confident, he leaves. Minutes later, it explodes. Plaster flies, windows shatter. But Hitler survives—saved by the thick table leg deflecting the blast and his slight repositioning.

Four people die, but not the target. Hitler’s trousers were shredded, and he suffered burst eardrums.

The conspirators were swiftly executed, some within 24 hours. Hitler ordered a brutal purge: over 7,000 arrested, nearly 5,000 executed. A historic plot undone by furniture. If conspiracies were airplanes, this one crash-landed before leaving the hangar.^[10]