The Most Intense Spy Missions In Military History

In the movies, spies take on some really daring missions and rarely seem to think twice about how poorly it could all end. In real life, these missions typically aren’t anything like they appear in James Bond films. Military spy operations take loads of planning and strategic action. There have been many interesting examples of amazing covert activities throughout history, involving forces all over the globe. As you read on, you’ll learn about some of the wildest spy missions ever.

A Navy Commando Ran Weapons Through Greece And The Balkan Peninsula

william donovan
MPI/Getty Images
MPI/Getty Images

Jack Taylor, often referred to as America’s first Navy SEAL, assisted in the Office of Strategic Services in the Balkan Peninsula. When this was his post, he and his troops managed to survey enemy troops and supply positions.

Taylor would resupply friendly forces and did night time raids thanks to the intel he reconnoitered. They almost caught him three times, but he escaped each occasion. Major William Donovan recommended that Taylor get a service cross for his efforts.

Harriet Tubman Joins The Union Army

with her hands folded
Smith Collection/Gado/Getty Images
Smith Collection/Gado/Getty Images

The story of how Harriet Tubman led the slaves to freedom is well-known and very important in history, but she also did something else impactful. When the Civil War started, she helped once again by joining the Union Army.

She used her skills to build a ring of spies, map territory, and to gather human intelligence about Confederate movements. Tubman became the first and only woman to lead a military operation in the heat of the Civil War. She would free 700 local slaves in the process.

Virginia Hall, The Great Spy

the spy -89864144
Apic/Getty Images
Apic/Getty Images

Virginia Hall had hopes of working in the foreign service, but she lost her foot in an accident before WWII. She would become a spy instead. In her new career, her brightest moment came when she snuck into France and led sabotage and intelligence-gathering missions.

She also trained three battalions, and they would do some incredible things. Overall, they eliminated 150 Germans and secured 500 more. Hall and her team didn’t stop before dismantling four bridges.

Call Her Agent Fifi

Agent Fifi
Robyn Elliot Author/Pinterest
Robyn Elliot Author/Pinterest

Marie Chilver, code-named “Agent Fifi,” was an English-born woman raised all over Europe. She was jailed in an internment camp in 1940 but managed to flee to England in 1941.

Unable to secure a job as a spy in France, she became a temptress for British spy trainees. Agent Fifi would approach agents and try to get information from them. If anyone told, they were quickly dropped from the program.

George Blake Becomes A Double Agent

the double agent
Crown/Mirrorpix/Mirrorpix via Getty Images
Crown/Mirrorpix/Mirrorpix via Getty Images

George Blake was a British MI6 agent during WWII. He was captured during the Korean War and had to serve three-year detention. In that time span, he became a communist and chose to betray his country.

He returned to Britain a hero in 1953, but quietly started his double agent work, betraying more than 40 MI6 agents and dismantling their operations. A Polish defector exposed Blake in 1961, leading to 42 years of prison. The bars didn’t hold him back as he escaped in 1966 and made his way to Moscow, where he received the Order of Friendship from Vladimir Putin.

CIA Turned Double Agent

soviet union double agent
LUKE FRAZZA/AFP via Getty Images
LUKE FRAZZA/AFP via Getty Images

Aldrich Ames was a CIA veteran before he decided to switch sides and become a double agent for the Soviet State Security Committee (KGB). The FBI arrested him and his wife in 1994 for spying for the Soviets.

During the investigation into his actions, news came out that he had spied for the KGB since 1985, given details about HUMINT sources, provided top-secret information via “dead drops,” and passed along classified operations against the USSR in exchange for millions.

Rescuing Jessica Lynch

saving  Jessica Lynch
David S. Holloway/Getty Images
David S. Holloway/Getty Images

Jessica Lynch was a supply clerk U.S. soldier. Iraqi forces captured her on March 23, 2003, after they ambushed her convoy when they took a wrong turn in Nassiriya. They couldn’t find her for nine days.

Finally, on April 1, a Special Operations Forces did a nighttime raid on her location. She was in a hospital with the bodies of eight other U.S. soldiers. The mission was a success, and they brought her back home.

It’s Agent 355

the woman of revolutionary war
Joe Sohm/Visions of America/Universal Images Group via Getty Images
Joe Sohm/Visions of America/Universal Images Group via Getty Images

There weren’t many women who participated in espionage during the Revolutionary War. There was, however, the Culper Spy Ring, which featured an obscure agent known as 355. That was the groups’ code number for the word “woman.”

She used the secret name to protect herself and her family, but her contributions are remembered in history. Agent 355 played a part in many missions, including the operation that helped arrest Major John Andre, head of England’s intelligence operations in the Big Apple.

Rose Greenhow, The Confederate Spy

Civil war spy
Encyclopaedia Britannica/UIG Via Getty Images
Encyclopaedia Britannica/UIG Via Getty Images

Rose Greenhow was a Confederate spy who established her network in Washington, D.C., at the start of the Civil War. She proved she was a prominent figure during this war with her skills that helped the South win the Battle of Bull Run thanks to her intelligence.

One of her most valuable feats was gaining vital information about the Union wanting to attack in Manassas, Virginia. She suffered death at sea transporting Confederate dispatches on a blockade-runner.

Oleg Gordievsky Shifted The Balance Of Power

Oleg Gordievsky spy
David Levenson/Getty Images
David Levenson/Getty Images

Oleg Gordievsky spied for the MI6 for 11 years while he worked as a KGB officer in London. Not the easiest thing to pull off, but he did it. He wouldn’t join the MI6 until 1972 after a Czech spy referred him.

For a decade, he gave MI6 intel about KGB operations and their attempts to sway western elections. Gordievsky earned credit for shifting the balance of power in the Cold War. He became one of the highest-ranking KGB officers to lead western espionage.

A Former FBI Agent Goes Soviet

former FBI agent
FBI/Newsmakers
FBI/Newsmakers

Robert Hanssen was an FBI agent who spied for the Soviet and Russian intelligence for more than two decades ending in 2001. His espionage still translates to doing some of the most damage in American history.

One of his missions included working with Moscow. He would deliver an incredible amount of classified information, revealing who the key players were in regards to America’s nuclear operations. Hanssen received millions in diamonds and cash for his traitor behavior. The FBI finally figured him out and indicted Hanssen on 21 counts of spying.

Christine Granville’s Rescue Mission

polish spy
Apic/Getty Images
Apic/Getty Images

Christine Granville had built a reputation for exploits during WWII, but her most courageous one was a rescue mission. Her goal was to release three other spies who were slated for execution in prison, which is no easy task.

Even with wanted posters of her face all over the country, she convinced the guards she was a British spy and a niece to a British general. She gave them the bright idea of releasing the spies in return for future mercy and payment. The Germans agreed to the deal, and she made it out with her pals.

First American Citizens Convicted For Spying

cold war
Universal History Archive/Getty Images
Universal History Archive/Getty Images

When it comes to atomic bombs, they’re the last thing you want to be involved with; just ask the Rosenbergs. Ethel and Julius Rosenberg got caught up in 1950 thanks to Ethel’s younger brother, David Greenglass. He worked in an atomic bomb lab and confessed to giving intel to the Soviets.

The Los Angeles Times reported that the Rosenbergs attempted “their best to give the Soviets top atomic secrets from the Manhattan Project, they succeed in handing over top military data on sonar and on radar that was used by [Moscow] to shoot down American planes in the Korean and Vietnam Wars.” The Rosenbergs got the electric chair in 1953.

Kitty’s Little Secret

Kitty Schmidt
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ullstein bild/ullstein bild via Getty Images

A woman by the name of Kitty Schmidt operated the most luxurious brothel you could go to in Berlin when Hitler came into power. Schmidt wasn’t fond of the Nazi regime, so she transported her money to British banks through Jewish refugees she helped escape until she got caught for trying to flee.

Upon interrogation, they asked if she would like to go to a concentration camp or keep her brothel open for spy business. She went with the latter, and her venue would become the hot spot for debriefing foreign diplomats and military personnel. The building finally got damaged by bombings after four years of espionage.

Rescuing O’Grady

coming back home
Peter Turnley/Corbis/VCG via Getty Images
Peter Turnley/Corbis/VCG via Getty Images

While Scott O’Grady flew his fighter jet on June 2, 1995, he got a hit by a Serbian missile. The U.S. Air Force Captain was on a mission and flying over Bosnia when it happened, but he used his ejection seat successfully.

Unfortunately, he landed in Serb-held territory. O’Grady spent six nights hiding out until his radio signal finally guided U.S. Marines to his location. They found him and brought the captain back, and the movie Behind Enemy Lines supposedly stems from his story.

Ending bin Laden

riding a horse
Getty Images
Getty Images

In 2011, the-then Commander in Chief made orders to an elite team of U.S. SEALs to handle Osama bin Laden. The attack was to take place in Abbottabad, Pakistan.

The SEALs succeeded in killing bin Laden and recovered what they called a “treasure trove” of information. The plan was so secretive that only a few U.S. officials knew about the plotting. It was a result of years of intelligence-gathering, stalking, and several months of extensive planning.

This Jazz Singer Smuggled Info In Her Undergarments

a spy in disguise
Hulton Archive/Getty Images
Hulton Archive/Getty Images

Josephine Baker was a dancer and a famous Jazz singer from America. In 1937, she became a French citizen, but after France fell to the Germans, the Axis believed her when she said she was on their side.

Over the next few years, she was a spy for the Allies. Her method of smuggling intelligence was genius. Baker would plan shows with neutral countries and give her sheet music with invisible ink to the Allies. If she needed photos, they would go in her undergarments.

Call Him The Spymaster

the spymaster
Ken Welsh/*/Design Pics/Corbis via Getty Images
Ken Welsh/*/Design Pics/Corbis via Getty Images

When you’re a spy, and you go by the name of Spymaster, then you’re probably one of the best to do it. Francis Walsingham served Queen Elizabeth I and was the Principal Secretary of State for the Tudors before becoming a master spy.

He’s the one responsible for finding out about the Babington Plot of 1586, which resulted in the execution-style death of Mary, Queen of Scots in 1587. Walsingham intercepted a return letter Mary wrote and copied the letter so he could forge a threatening message on the bottom to show to Elizabeth. That’s when he convinced the Queen to end Mary’s life.

Freeing Benito Mussolini

freeing Mussolini
Express/Express/Getty Images
Express/Express/Getty Images

After the Allies successfully invaded Sicily, Italian government officials gave up Benito Mussolini. They transported him throughout Italy before placing him in an old hotel in the Apennine mountains. Hitler became worried, so he ordered Otto Skorzeny to apprehend Mussolini before the Italians joined the Allies.

The Italians moved the dictator around in hopes of keeping his location a secret, but Skorzeny intercepted a radio message about Mussolini’s trail. Only a few months after the initial capture, Skorzeny sent paratroopers tot he hotel Mussolini was at and secured him without firing a shot.

Fooling The Nazis

operation mincemeat
realtimewwii/Twitter
realtimewwii/Twitter

The Allies needed to invade a heavily protected Sicily in 1943. They obtained the dead body of a vagrant, put him in a uniform, attached a briefcase to his wrist filled with fake plans of invasion for Greece, and made him float in the ocean currents to “neutral” Spain.

After the Nazis found the body, they prepped for an invasion at the wrong location. As a result, thousands of Allies remained alive during the invasion of Sicily.