25 Boldest Assassination Attempts Ever
History is littered with moments where a single act of violence — or the stunning failure of one — changed the course of civilization. Assassination attempts have targeted emperors, presidents, religious leaders, and revolutionaries, often unfolding in the most dramatic, unexpected, and audacious ways imaginable. Some succeeded. Many failed. All of them left a permanent mark on history.
What separates a “bold” assassination attempt from an ordinary act of violence? It’s the sheer audacity of the plan, the impossibility of the odds, the spectacular public settings, or the sheer stubbornness of fate that keeps the target alive against all reason. These are the attempts that make you stop and think — how did that almost work? How did anyone survive that? How did the world nearly change in an instant?
From ancient Rome to 21st-century Georgia, this definitive list of the 25 boldest assassination attempts ever covers a sweeping range of history, geography, and method. Whether you’re a history enthusiast or simply a fan of stranger-than-fiction stories, these accounts will leave you genuinely stunned.
What Makes an Assassination Attempt “Bold”?
Before diving in, it’s worth establishing what qualifies these particular attempts as the boldest. Not every assassination plot makes this list simply because the target was famous. The “boldness” factor comes down to one or more of these defining criteria:
– Audacious planning — elaborate, multi-layered plots that required extraordinary risk
– High-security environments — attempts made where security should have been impenetrable
– Public spectacle — carried out in front of large crowds or during major events
– Unlikely survival — targets who survived against impossible odds
– Historical shockwaves — attempts whose success or failure fundamentally redirected world history
– Unusual or creative methods — especially inventive or bizarre approaches to a very grim goal
With those criteria in mind, here are 25 of the most audacious assassination attempts ever recorded.
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The 25 Boldest Assassination Attempts in History
1. Julius Caesar (44 BC)
The most dramatic political murder of the ancient world happened in the open, in the Roman Senate, on the Ides of March, 44 BC. A conspiracy of approximately 60 Roman senators — calling themselves the Liberatores — surrounded Julius Caesar and stabbed him 23 times. The boldness here is staggering: this wasn’t a shadowy midnight attack. It was a coordinated, broad-daylight assassination carried out by some of the most powerful men in Rome, right in the heart of Roman political life. The act triggered a civil war and ultimately dismantled the Roman Republic it was meant to save.
2. King George III at Drury Lane (1800)
On May 15, 1800, James Hadfield fired a pistol at King George III in the royal box at Drury Lane Theatre in London. Hadfield, a war veteran suffering from severe head injuries and mental illness, deliberately missed — believing his execution for the attempt would fulfill a divine prophecy. The king reportedly remained completely calm after the shot. The incident directly led to the Criminal Lunacy Act of 1800, fundamentally changing how British law handled mental illness in criminal cases.
3. Napoleon Bonaparte and the Infernal Machine (1800)
On December 24, 1800 — Christmas Eve — royalist conspirators detonated a massive bomb-laden cart on the Rue Saint-Nicaise in Paris, just seconds after Napoleon’s carriage passed by. The explosion killed 22 people and wounded 56 more, but Napoleon escaped unharmed. What makes this attempt truly bold is the scale: it was essentially a 19th-century car bomb deployed in the middle of Paris. Napoleon, furious and undeterred, used the attack as justification to exile or execute hundreds of political opponents.
4. Andrew Jackson’s Double Misfire (1835)
On January 30, 1835, Richard Lawrence approached President Andrew Jackson on the steps of the U.S. Capitol and fired two pistols at him from close range. Both guns misfired. Jackson, enraged rather than frightened, began beating Lawrence with his walking cane until bystanders restrained him. Mathematicians later calculated the odds of both pistols misfiring in dry conditions at roughly 1 in 125,000. This was the first assassination attempt on an American president, and Jackson walked away convinced his political enemies had orchestrated it.
5. Queen Victoria’s Remarkable Run of Survival (1840–1882)
Queen Victoria survived no fewer than eight separate assassination attempts over the course of her reign — a record that speaks to both the dangers of her era and her remarkable composure under fire. The attempts ranged from point-blank pistol shots to a walking stick attack. Rather than retreating from public life, Victoria continued making public appearances after each incident, earning widespread admiration for her stoicism. Her very public survival arguably strengthened the monarchy during a politically turbulent period in British history.
6. Abraham Lincoln at Ford’s Theatre (1865)
John Wilkes Booth’s assassination of President Abraham Lincoln on April 14, 1865, was bold not just in its execution but in its broader scope. Booth coordinated simultaneous attacks on Vice President Andrew Johnson and Secretary of State William Seward that same night — a planned decapitation of the Union government. Only the Lincoln attack succeeded. Booth shot the president in the back of the head during a packed performance at Ford’s Theatre in Washington, D.C., then leapt dramatically to the stage, breaking his leg. The audacity of a coordinated three-pronged political strike makes this one of the most ambitious assassination plots in American history.
7. Alexander II of Russia and the Bomb Squad (1881)
Tsar Alexander II had survived so many assassination attempts that he was nicknamed “The Tsar Liberator” by some and hunted obsessively by the revolutionary group Narodnaya Volya. On March 13, 1881, the group deployed a three-stage assassination plan. When the first bomb failed to kill him, Alexander stepped out of his carriage — and a second bomber threw another explosive directly at his feet. The tsar died hours later. What makes this attempt staggering is the tactical sophistication: the group stationed multiple bombers in sequence, ensuring that even if the first attempt failed, the second would succeed.
8. Grigori Rasputin’s Impossible Death (1916)
The assassination of Grigori Rasputin on December 30, 1916, reads more like dark comedy than historical fact — but it actually happened. Prince Felix Yusupov and a group of Russian nobles invited Rasputin to a palace, fed him wine and cakes laced with cyanide, shot him when the poison failed, shot him again when he got up and tried to escape, beat him, and finally drowned him in the Neva River. Whether all the details are precisely accurate remains debated by historians, but the extraordinary difficulty the assassins had in killing him cemented Rasputin’s almost mythological status in Russian history.
9. Archduke Franz Ferdinand’s Fateful Wrong Turn (1914)
The assassination that triggered World War I very nearly didn’t happen. On June 28, 1914, Gavrilo Princip and a group of six conspirators positioned themselves along the Archduke’s motorcade route in Sarajevo. The first attempt failed when a bomb bounced off the Archduke’s car. Princip, convinced the mission had failed, went to a nearby deli to get something to eat — only for the Archduke’s driver to make a wrong turn and stop the car directly in front of him. Princip stepped forward and fired two shots. The sheer improbability of those circumstances — a chance encounter that ignited a world war — is what makes this one of history’s most chilling examples of fate’s role in assassination.
10. Theodore Roosevelt Gives a Speech With a Bullet in His Chest (1912)
On October 14, 1912, John Schrank shot Theodore Roosevelt in the chest during a campaign stop in Milwaukee, Wisconsin. The bullet was slowed by Roosevelt’s steel eyeglass case and a 50-page copy of his speech folded in his breast pocket. Rather than seeking immediate medical attention, Roosevelt delivered a 90-minute speech to the crowd — beginning with the now-legendary line, “Ladies and gentlemen, I don’t know whether you fully understand that I have just been shot.” The bullet remained lodged in his chest for the rest of his life. The sheer stubbornness of this response cements it as one of the boldest moments in political history.
11. Franklin D. Roosevelt’s Near Miss in Miami (1933)
Just weeks before taking office, President-elect Franklin D. Roosevelt narrowly escaped assassination on February 15, 1933. Giuseppe Zangara, an Italian-born bricklayer, fired five shots at Roosevelt during a public rally in Miami’s Bayfront Park. A woman in the crowd grabbed Zangara’s arm at the critical moment, throwing off his aim. Roosevelt was unharmed, but Chicago Mayor Anton Cermak, who had just shaken Roosevelt’s hand, was shot and died 19 days later. Zangara claimed he hated all rulers and presidents. He was executed just 33 days after the attack — one of the fastest executions in American legal history.
12. Mahatma Gandhi and the Price of Nonviolence (1948)
Gandhi survived at least two serious assassination attempts before Nathuram Godse finally succeeded on January 30, 1948, at Birla House in New Delhi. A bomb had been thrown at a prayer meeting he attended just ten days earlier. Gandhi’s philosophy of radical nonviolence, which put him in direct conflict with Hindu nationalists, made him a target precisely because of his enormous moral authority. He was shot three times at close range while greeting a crowd of devotees. The killing shocked the world and, tragically, demonstrated that advocating peace had become Gandhi’s greatest vulnerability.
13. Fidel Castro and the CIA’s Creative Desperation (1950s–1980s)
No figure on this list inspired more assassination plots than Fidel Castro. The CIA reportedly devised over 600 plans to kill him — an astonishing testament to his seemingly supernatural ability to survive. The plots included an exploding cigar, a poisoned wetsuit, a seashell rigged with explosives on his favorite diving spot, and a plan to use thallium salts to make his iconic beard fall out and undermine his image. Most plots never reached execution stage, but several came genuinely close. Castro himself once remarked, “If surviving assassination attempts were an Olympic event, I would win the gold medal.”
14. John F. Kennedy in Dallas (1963)
The assassination of President John F. Kennedy on November 22, 1963, remains the most analyzed killing in American history. Lee Harvey Oswald fired three shots from the sixth floor of the Texas School Book Depository as Kennedy’s motorcade moved through Dealey Plaza in Dallas — an audacious, publicly staged attack on the most powerfully protected man in the world. Kennedy was rushed to Parkland Memorial Hospital but died 30 minutes after being shot. The assassination triggered decades of conspiracy theories, led to sweeping changes in presidential security protocol, and shattered American political innocence in a way the country is still processing.
15. Robert F. Kennedy in the Ambassador Hotel (1968)
Just two months after the assassination of Martin Luther King Jr., Senator Robert F. Kennedy was shot by Sirhan Sirhan on June 5, 1968, in the kitchen pantry of the Ambassador Hotel in Los Angeles, moments after winning the California Democratic primary. Kennedy was en route to potentially becoming president. The setting — a crowded hotel kitchen corridor, surrounded by supporters — made the attack both unexpected and horrifyingly intimate. RFK died the following day. The back-to-back political killings of 1968 sent shockwaves through American democracy that resonate to this day.
16. Martin Luther King Jr. in Memphis (1968)
On April 4, 1968, James Earl Ray shot Dr. Martin Luther King Jr. on the balcony of the Lorraine Motel in Memphis, Tennessee, where King was supporting a sanitation workers’ strike. The assassination of arguably the most powerful voice for civil rights in American history sparked riots in more than 100 cities across the United States. Ray fired a single rifle shot from a rooming house bathroom window across the street — a painstakingly deliberate act that highlighted how high a price peaceful leadership can carry. The killing remains a defining wound in American social history.
17. Pope John Paul II in St. Peter’s Square (1981)
On May 13, 1981, Mehmet Ali Ağca shot Pope John Paul II four times in St. Peter’s Square, Rome, as the pope’s vehicle moved through a crowd of 20,000 pilgrims. The pope survived after extensive emergency surgery. What makes this attempt particularly audacious is the setting: the very heart of the Catholic world, in front of tens of thousands of faithful, in broad daylight. John Paul II later visited Ağca in prison and publicly forgave him — a gesture of remarkable grace that itself became a defining moment of his papacy. The shooter’s full motivations and potential connections to Eastern European intelligence services were never definitively established.
18. Anwar Sadat During a Military Parade (1981)
On October 6, 1981, Egyptian President Anwar Sadat was assassinated during the annual victory parade commemorating the Yom Kippur War in Cairo. Islamic extremist soldiers within the parade itself opened fire with automatic weapons and threw grenades at the reviewing stand where Sadat sat. The boldness was extraordinary: the attack came from within the military during one of Egypt’s most prominent national ceremonies. Sadat had recently signed the Camp David Accords with Israel — a peace deal that made him a hero internationally and a target domestically. Ten others were killed alongside him.
19. Ronald Reagan Outside the Washington Hilton (1981)
On March 30, 1981 — just 69 days into his presidency — Ronald Reagan was shot by John Hinckley Jr. outside the Washington Hilton Hotel. Hinckley fired six shots in 1.7 seconds, hitting Reagan, Press Secretary James Brady, a Secret Service agent, and a police officer. A bullet lodged within an inch of Reagan’s heart. At 70, he became the oldest president to survive an assassination attempt, and his reportedly unflappable humor in the operating room — “I hope you’re all Republicans” — became legendary. Press Secretary James Brady was left permanently disabled, and the attack ultimately spurred passage of the Brady Handgun Violence Prevention Act.
20. Queen Elizabeth II’s Blank Shots (1981)
On June 13, 1981, during the annual Trooping the Colour ceremony on The Mall in London, 17-year-old Marcus Sarjeant fired six blank shots at Queen Elizabeth II as she rode her horse past. The queen’s horse startled, but she brought it under control with what eyewitnesses described as remarkable composure and rode on to complete the ceremony. Sarjeant was arrested almost immediately. The incident exposed significant vulnerabilities in royal security — the route was lined with spectators, and Sarjeant had simply walked up and fired. Parliament quickly passed the Treason Act 1842 Amendment specifically in response.
21. Indira Gandhi and the Betrayal Within (1984)
Few assassinations in history carry the visceral weight of Indira Gandhi’s death on October 31, 1984. She was shot 31 times by two of her own Sikh bodyguards — Satwant Singh and Beant Singh — in the garden of her official residence in New Delhi. The assassination came in direct retaliation for Operation Blue Star, the military storming of the Golden Temple in Amritsar that Gandhi had ordered months earlier. The betrayal by her own trusted security detail made this killing uniquely devastating, and the violence it triggered — anti-Sikh riots across India killed an estimated 3,000 people — demonstrated how a single act of violence can cascade into mass tragedy.
22. Benazir Bhutto’s Final Campaign (2007)
Benazir Bhutto, Pakistan’s former prime minister and the first woman to lead a Muslim-majority nation, survived one major assassination attempt in Karachi on October 18, 2007, when a suicide bomber killed 136 people around her motorcade. She refused to stop campaigning. On December 27, 2007, a gunman opened fire on her at a campaign rally in Rawalpindi, and a suicide bomber detonated immediately after — killing her and more than 20 others. The attempts on her life were brazen demonstrations of force against a charismatic, pro-democracy leader in a country where such leaders face existential risk. Her courage in continuing to campaign despite credible threats remains extraordinary.
23. George W. Bush and the Grenade in Georgia (2005)
On May 10, 2005, Vladimir Arutyunian threw a live Soviet-era grenade at the podium where President George W. Bush was speaking in Freedom Square, Tbilisi, Georgia — just 61 feet away from the president. The grenade landed near the podium but failed to detonate because a red tartan handkerchief wrapped around it slowed its rotation and prevented the pin from releasing properly. Had it detonated, it could have killed both Bush and Georgian President Mikheil Saakashvili, along with dozens of spectators. It ranks as one of the most direct attempts on a sitting American president in modern history, and the fact that a piece of fabric saved two heads of state makes it one of history’s most improbable near-misses.
24. Adolf Hitler and the July 20 Plot (1944)
Operation Valkyrie is arguably the most elaborate assassination attempt of the 20th century. On July 20, 1944, Colonel Claus von Stauffenberg smuggled a briefcase bomb into Hitler’s Wolf’s Lair headquarters in East Prussia, placed it under the conference table, and slipped out before the detonation. The explosion killed four people — but Hitler survived with minor injuries. A colleague had inadvertently moved the briefcase to the far side of a heavy oak table leg, which absorbed much of the blast. The conspiracy involved hundreds of German military officers and civilians willing to risk everything, including their lives, to end the war. After the plot failed, over 5,000 people were executed in the reprisals that followed.
25. The Attempted Killing of Malala Yousafzai (2012)
On October 9, 2012, a Taliban gunman boarded a school bus in Pakistan’s Swat Valley, asked which girl was Malala Yousafzai, and shot the 15-year-old activist in the head. The attack targeted a teenager who had been publicly advocating for girls’ education — making it an act of particular brutality and international significance. Malala survived after extensive surgeries in Pakistan and the United Kingdom. Rather than silencing her, the attempt amplified her voice: she went on to become the youngest-ever recipient of the Nobel Peace Prize in 2014. No assassination attempt on this list more powerfully illustrates how the act of silencing someone can instead ignite a movement.
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Common Threads in Bold Assassination Attempts
The Role of Luck and Chance
Read through these 25 accounts and one theme becomes impossible to ignore: luck — in both directions — is the most powerful force in assassination history. A wrong turn in Sarajevo. A tartan handkerchief in Tbilisi. A thick speech manuscript in Milwaukee. A bystander grabbing a shooter’s arm in Miami. History turns on these micro-moments with terrifying frequency. Many of the world’s most consequential leaders survived not because of superior security, but because of improbable accidents. Many victims died not because of superior planning, but because fate offered no such intervention.
Evolving Methods and Countermeasures
The methods across these 25 attempts reveal a grim arms race between would-be assassins and security apparatus. Early attempts relied on proximity and bladed weapons. Firearms democratized assassination, making it possible from greater distances. The 20th century brought bombs, coordinated multi-target attacks, and eventually, suicide bombing as a tactic. Each major attempt typically triggered sweeping changes in presidential or royal security protocols — the Kennedy assassination transformed U.S. Secret Service operations; the Reagan attempt prompted changes in hospital emergency protocols; the Bhutto assassination reshaped Pakistani political security.
The Enduring Impact on History
Perhaps the most sobering conclusion from these accounts is how dramatically successful assassinations — and near-successful ones — redirect the flow of history. World War I traces directly to a wrong turn in Sarajevo. The trajectory of India’s independence movement was altered by Gandhi’s death. The Camp David peace process in the Middle East lost its most important Egyptian advocate when Sadat was killed. Even failed attempts reshape history: the July 20 Plot’s failure extended WWII by months, costing hundreds of thousands of lives. These are not footnotes — they are fulcrum points.
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Frequently Asked Questions
What is the boldest assassination attempt in history?
This is genuinely subjective, but many historians point to the July 20 Plot against Adolf Hitler as the most elaborate and consequential failed attempt, given its sophisticated planning, the enormous number of co-conspirators, and the catastrophic reprisals that followed its failure.
Which world leader has survived the most assassination attempts?
Fidel Castro holds the widely cited record, with some estimates claiming over 600 documented or alleged plots against his life. Many never reached execution stage, but the sheer volume and creativity of attempts — organized largely by the CIA — is historically unprecedented.
What was the first assassination attempt on a U.S. president?
The first recorded attempt on a sitting U.S. president was Richard Lawrence’s attack on Andrew Jackson on January 30, 1835. Both of Lawrence’s pistols misfired at close range, and Jackson proceeded to beat his attacker with a walking cane.
Which assassination attempts had the greatest historical consequences?
The assassination of Archduke Franz Ferdinand in 1914 is widely considered the most consequential in modern history, as it triggered a chain of events that led directly to World War I. Abraham Lincoln’s assassination fundamentally altered the post-Civil War Reconstruction era.
How has presidential security changed because of assassination attempts?
Each major attempt has prompted reforms. After Kennedy’s assassination, the Secret Service was dramatically expanded and restructured. The Reagan attempt changed security perimeters around public venues and contributed to the Brady Bill, which imposed background checks on firearm purchases in the United States.
What was unusual about the attempt on Malala Yousafzai?
Most targets on this list were heads of state, political figures, or military leaders. Malala was a 15-year-old student activist targeted specifically for advocating education for girls — making the attack both uniquely chilling and, ultimately, counterproductive to the perpetrators’ goals.
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A Legacy of Audacity and Resilience
These 25 boldest assassination attempts span more than 2,000 years of human history, crossing continents, cultures, and political systems. What emerges from them collectively is a portrait of something fundamental about power, fear, and the human impulse to change history through a single decisive act. Sometimes it works. Far more often than history remembers, it doesn’t — foiled by a wrong turn, a misfire, a brave bystander, or a folded speech manuscript.
What these accounts also reveal is resilience. Not just the physical survival of men and women like Theodore Roosevelt, Ronald Reagan, or Malala Yousafzai — but the resilience of ideas. The people who ordered or carried out these attacks typically wanted to silence a voice, stop a movement, or prevent a future. In virtually every case on this list, they failed at that deeper objective, even when the bullet found its mark.
History, it turns out, is harder to kill than any individual within it.