10 of The Most Craziest Characters In History

A British soldier fighting in the two World Wars was shot in ears, eye, hips, ankle, and ribs but survived. He tore off his own fingers when the surgeon didn’t want to amputate them. He was captured but escaped and captured again, then went on to write a book in which he claimed he frankly “enjoyed the war.”

Lieutenant General Adrian Carton de Wiart defied death so many times in his life that his story almost sounds like folklore, except that it is not. Born in Brussels, Belgium in 1880, he joined the British Army without getting his father’s permission after dropping out of Oxford College. He wasn’t even a British citizen, but he falsified his name and age. Soon after enlisting, he was sent to South Africa to fight in the Second Boer War. Fighting in the war, he was shot in the belly and groin, and therefore he had to go back to England for treatment. That was just the start of his hard-to-believe career and the first of the many injuries that were to come.

Adrian was in Somalia in 1914 when the First World War had started and was trying to capture a fort held by the enemy. This time, he was shot in the eye, and another bullet struck his ear. This left him blind in one eye, but this also allowed him to get out of Somali and move to England where, according to him, the real action going on. He continued fighting on the Western Front where he was again shot in head, hips, ear, ankle, and ribs. One of his hands was also severely damaged that when a surgeon said that said that his fingers of the damaged hand didn’t require amputation, he tore them off. His hand was eventually amputated.

In Second World War, 60-year-old Adrian was sent on a mission to Yugoslavia, but his plane started malfunctioning midair over the Mediterranean Sea. It was actually shot down. He fell into the cold water a mile away from land but swam to shore only to be captured and taken as a prisoner by the Italians.

He managed to escape from the camp he was taken to only after two days but was recaptured after enjoying freedom for eight days. He made four more failed attempts to flee. He was kept a prisoner there for two years before being released in 1943. Adrian later went on to write his autobiography Happy Odyssey in which he wrote: “Frankly, I enjoyed the war.”

Michael I became King of Romania when he was just five. His family was friends with Hitler, but he sided with the Allies, only to be occupied by USSR after the war was won. He received the highest Soviet honor and Legion of Merit from the USA. He remained in exile for most of his life working as a farmer, pilot, and stockbroker.  

Michael I, the last King of Romania, wasn’t really a crazy character like many others in this list, but his life was really a crazy one. He lived an incredibly sad and unstable life which forced him to become a chicken farmer at one point of time, a pilot at another, and a stockbroker yet another time, all while he was technically the king of Romania.

Born in 1921, King Michael was the son of King Carol II and Queen Helen. His father was the reason for most of his hardship growing up. Shortly after his birth in 1925, his father eloped with his mistress, Elena Magda Lupescu, renouncing his rights to the throne. When, in 1927, his grandfather King Ferdinand died, he was made the King before his sixth birthday. He reigned for three years before his father returned in 1930 and became the king. His mother Helen was exiled, and King Carol II tried to replace her with his mistress. He reigned until 1940 after which a pro-Nazi military dictator, Marshal Ion Antonescu, ousted him for being anti-German by staging a coup and reinstalling 18-year-old King Michael as a “puppet” King. After tolerating Marshal for years and establishing secret relationships with the Allies, he orchestrated a coup against Marshal and arrested him in 1944. He broke Romania’s alliance with Germany shocking Hitler and sided with the Allies. His move cut short the Second World War by about six months. But once the war was over, the USSR occupied his country. For his move, he was awarded the highest degree, Chief Commander of the American Legion of Merit by U.S. President Harry S. Truman as well as the Soviet Order of Victory by Joseph Stalin. But then, his country was occupied by the USSR.

Frustrated, he went on a strike and refused to sign any decree of the communist government. But under the pressure of the Allies, he could not do much. In December 1947 when he returned to Romania after attending a marriage, he was made to sign his own abdication at gunpoint and was exiled. He could not return to his own land for the next four decades. While in exile, he married Princess Anne of Bourbon-Parma in 1948. In 1990, after 43 years, he returned to Romania with a 24-hour visa but was forced to leave by the police before that. Two years later, he was allowed to return to Romania to celebrate Easter, but seeing his immense popularity among people, he was not allowed to enter the country again by the ruling government. But in 1997, the government was replaced by a new one, and this time his citizenship was restored.

After the restoration of his Romanian citizenship, he lived partly in Switzerland and partly in Romania until his death in 2017.

In the 1930s, an Irish alcoholic and homeless man survived despite being fed antifreeze, turpentine, poison, etc., by his acquaintances attempting insurance fraud. He even survived after being left in the snow and getting hit by a taxi. His ability to beat death earned him the nickname “Mike the Durable.”

Michael Malloy was a homeless Irish man who lived in New York in the 1920s and 1930s. He was a former firefighter and is famously remembered in history as “Mike the Durable” and “Iron Mike” who survived numerous murder attempts by five of his acquaintances who would have gained $3,500 through an insurance fraud if the ploy had succeeded. Tony Marino, Joseph “Red” Murphy, Francis Pasqua, Hershey Green, and Daniel Kriesberg together hatched the plan to kill Michael and prove the death accidental. They even had included a corrupt insurance agent in the plan and started to work on their plan in January.

Michael was an alcoholic and Marino, who was the owner of a speakeasy, thought that if he gave him unlimited credit, he would drink himself to death. But though Michael did abuse the credit and drank most of the time, he kept appearing in the bar for free liquor. Seeing the plan failing, they then started to mix antifreeze in his drinks, but still, it did nothing to him and he continued to drink as usual. Next, antifreeze was substituted with turpentine, then horse liniment and rat poison, but nothing could kill him.

At one time, Francis Pasqua claimed that he saw someone die after eating oysters with whiskey, so they made him eat raw oysters soaked in wood alcohol. This failed to kill him too. When they finally learned that nothing that Michael would ingest could kill him, they looked for other ways to kill him. One night they made him drink until he passed out. He was then carried outside and dumped in the snow. To make sure he would die, they poured 19 liters of cold water on his chest and left the scene. The following day, Michael appeared for his free drinks. After that, they hit him with a taxi moving at 72 kilometers per hour, but he recovered within three weeks and came back to the bar for more drinks.

Tired, they took a final approach and one night after he had passed out, they put a hose in his mouth and connected that to a gas jet. This killed him in an hour, and he was pronounced dead of lobar pneumonia. The police got suspicious when they heard stories of “Mike the Durable” in the town and eventually, the ploy was discovered. They were able to kill Michael finally, but never got the money they wanted.

Notorious pirate Benjamin Hornigold once attacked a ship just to take the hats of the people in the ship because, apparently, they got drunk the previous night and threw their own hats away.

Benjamin Hornigold operated during the golden age of piracy between the 1650s and 1730s, and though he had a brief career of only about six years starting from 1715, it was but a prolific one.

Nothing much is known about the early life of the notorious pirate, but it assumed that he might have born in Norfolk, England where the surname “Hornigold” is found. He started his career as a small-time looter off the coast of New Providence, a populous Island in the Bahamas. There, he had established a Privateers or Pirates’ Republic and quickly became a menace to the small merchant ships. He progressed quickly, and by 1717, he commanded a 30-gun sailing ship named Ranger. In fact, Ranger was the most heavily armed ship in the Bahamas at that time, and this helped him and his crew of about 350 pirates which he assembled to take control over other ships with impunity.

In March 1717, Hornigold attacked a vessel which was sent to capture pirates by the governor of South Carolina. The attack was so fierce that the crew of the pirate-hunting ship fled for their lives and later reported that Hornigold’s had five vessels in his possession.

“Hornigold” was a name that would send chills down the spines of the crews of the merchant ships, and thus in the year 1717 when he attacked a ship off the coast of Honduras, the terrified merchants begged for their lives. Strangely, Hornigold told them that they should not worry, and the only reason he and his crew had attacked the ship was so that they could take their hats. He explained that the previous night they all had gotten drunk and threw their hats into the sea. Hornigold let the ship and merchants go after taking their hats. Historians believe that he did that just to exhibit his powers. Nevertheless, this event remained the most memorable and craziest event of his career and of piracy in general.

Towards the end of 1717, his crew decided to overthrow him as he would not attack English ships. He fled in a small ship with a few loyal men and later in life became a pirate hunter for the governor of Bahamas, hunting down his old associates. He died in 1719 during a mission when his ship was caught in a hurricane and wrecked on a reef.

In the year 1859, a man named Joshua Norton declared himself the “Emperor of the United States and Protector of Mexico.” He ordered the dissolution of the US Congress and even issued his own currency. The restaurants accepted his currency, and 10,000 people attended his funeral.

Joshua Norton was born in England on February 4, 1818, but grew up in South Africa. When he was 30 years old and had lost both his parents, he arrived in San Francisco to start a new life. Initially, he made a living as a businessman, but due to bad investments in Peruvian Rice, he lost all his fortune and possibly had lost his sanity too. He tried to void his rice contract but lost the lawsuit.

On September 17, 1859, discontented with inadequacies of legal and political structures and presence of corruption, he decided to take matters in his own hand and declared himself the Emperor of the United States and assumed the title “Emperor Norton I.”He sent letters to the newspapers of the country proclaiming he was the emperor. Many newspapers actually carried the news for a humorous effect, but that was just the beginning of his imperial acts. Soon, he assumed a second title “Protector of Mexico.”

He went on to issue decrees ordering the abolition of the US Congress and summoned the US Army to oust the officials. Both the Army and the Congress chose to ignore him. Further, in 1869, he declared that the Democrat and Republic parties should be abolished. A few of his decrees were but visionary, like the decrees of forming a “League of Nations” and prohibition of conflicts among religious sects.

He issued his own currency which restaurants actually accepted. People in San Francisco generally had a warm approach towards him despite all his erratic and insane acts. People loved him and took care of him. When his clothes begun to look old, people bought him a new uniform suited for an emperor.

On January 8, 1880, Emperor Norton collapsed on a street and died. Reportedly, about 10,000 people attended the funeral held at the expense of the city of San Francisco, and his funeral cortège was five kilometers long.

Bill Millin, a Scottish bagpiper, marched up and down playing the bagpipe on the Normandy Beach while men fell around him dead. The Germans didn’t shoot him thinking he had gone mad.

Bill Millin was a Scottish bagpiper who was born in Canada to a father of Scottish origin. In 1922, when he was three years old, his father moved to Glasgow along with the family where he took the job of a policeman. Millian was therefore raised and educated in Glasgow.

Before the Second World War had begun, he joined the Territorial Army in Fort William and subsequently volunteered as a commando in 1941. While he was undergoing training at Achnacarry in Fort William, he met Brigadier Simon Christopher Joseph Fraser, the 15th Lord of Lovat, and the 4th Baron of Lovat. Lord Lovat offered him the job of his personal servant. Millin instead insisted that he should be appointed as his personal piper and he was made so.

He is best remembered for playing the bagpipe on the Normandy Beach during D-Day while the Germans fired and men collapsed around him. The Normandy landings, codenamed “Operation Neptune” and popularly known as “D-Day,” that took place on June 6, 1944, and is considered one of the bloodiest events of World War II. It is estimated that about 19,000 soldiers lost their lives that day when the Allied forces invaded Normandy, France that started the liberation of France from the German occupation.

Due to security reasons, the British had restricted the use of bagpipes in the battles, but Lord Lovat ignored the order and told Millian that he should not worry about the command as they both were Scottish and the rule didn’t apply to them. When his troop landed on the shore of Normandy, he started playing his bagpipe. He didn’t run but walked effortlessly concentrated on playing the instrument while the Germans showered mortars and fired at them. Soldiers fell around him but he neither stopped nor cared.

When the battle was won and the Germans were captured, he asked the snipers why they didn’t shoot him. The snipers answered that they had thought he had gone mad.

Jack Churchill, who is popularly known as “Mad Jack,” used to go into the battlefields in World War II equipped with a bow, a sword, and a bagpipe. He holds the record of the only confirmed longbow kill in the war.

Captain John Malcolm Thorpe Fleming Churchill, aka Jack Churchill, was a British officer who fought in the World War II armed with a broadsword, a bow, and a bagpipe. He was so dangerously old-schooled and unbelievably brave that he was nicknamed “Mad Jack”. He lived by the motto: “Any officer who goes into action without his sword is improperly dressed.”

In 1943 outside the city of Molina, Italy, he single-handedly captured 42 German soldiers using only his sword and bow and arrows, and in the process, he lost his sword. He later went back there to retrieve that. He and his troops in the year 1944 were captured by the Germans in Yugoslavia and were sent to a concentration camp. While they were being captured, he kept playing on his bagpipe the folk song “Will Ye No Come Back Again?”. He but managed to escape from there only to be recaptured and sent to Austria. He escaped from there too and walked 150 kilometers to Italy. He met an American officer in Italy who helped him to get back to England.

In 1945 he was sent to Burma to fight against the advancing Japanese, but as he reached India, the war ended with the bombings of Hiroshima and Nagasaki. Captain Jack Churchill was unhappy that the war had ended and complained that if it weren’t for the Americans, the war could have been continued for 10 more years.

He died in 1996 at 89 years of age. In 2014, the Norwegian Royal Explorers Club published a book about the world’s greatest adventures and he was ranked the greatest. 

A French-Canadian soldier, Leo Major, during World War II captured 93 German soldiers single-handedly in one night. A year later, he alone liberated an entire city from the Nazis.

French-Canadian soldier Leo Major was only 19 years old when he decided to join the Canadian Army in the year 1940 to prove his father that he was someone his father could be proud of. He always had a poor relationship with him and little did he know that this would result in him becoming one of the most impactful soldiers during the Second World War.

During the Battle of the Scheldt in the year 1944, he was given the task of military observation in Zeeland, the Netherlands on a cold and rainy day when he spotted two German soldiers walking along an embankment. Leo instantly attacked them and captured one of the soldiers. He tried to overpower the other using the captured soldier as bait, but the soldier tried to use his gun and Leo killed him before he could shoot at him. He went on to use the live soldier as bait and captured their commander. He shot three more soldiers dead which compelled others to surrender. He then proceeded to march all the captured soldiers, 93 in total, to the Canadian front line.

A year after that, in April 1945, he was near the city of Zwolle, the Netherlands along with his regiment. The city was occupied by German troops. While being there, the regiment’s commanding officer asked for volunteers who could check on the number of German soldiers against whom they would be fighting the next morning. Leo Major and another soldier, Corporal Willie Arseneault, quickly agreed to do the assessment. Corporal Willie Arseneault, however, was killed in the night when their positions were detected. This but only fueled Leo’s determination. In a fit of rage, he killed two enemy soldiers and the rest fled after witnessing this.

Leo continued alone and soon noticed a German vehicle. He took the driver hostage and made him drive to a bar where a German officer was drinking. First, he fought and took the officer hostage but decided to take a calculated risk of letting him go after telling him that the Canadian artillery would start firing at the German troops at 6:00 am and it would cause huge causalities. After letting the officer go, he went around the city causing as much noise as possible to terrify the German troops throwing grenades and firing a sub-machine gun. He also captured groups of Nazi soldiers and marched them to the Canadian front line. He set the Gestapo HQ on fire and fought with eight enemy soldiers in the SS HQ. In the fight, he killed four while others fled quickly.

The terrified German troops vacated the city by 4:30 a.m. and Zwolle was liberated by a single man.

Digby Tatham Warter, a World War II British officer. used to carry an umbrella into the battlefield and once overpowered a German vehicle by poking the driver in the eye with the umbrella.

It was the dream of Digby Tatham-Warter to join the British-Indian Army and had graduated from Sandhurst Military College. But after the death of his brother at the Second Battle of El Alamein in 1942, he volunteered for the airborne forces. Digby’s father was a World War I veteran and had died in the war too. He was soon transferred to the Parachute Regiment.

Digby today is remembered, besides his bravery, for his unusual way of fighting battles while carrying an umbrella with him always. In the Parachute Regiment, he was made the commander of A Company in the Second Parachute Battalion. Before the company was to be deployed in September 1944 for the Battle of Arnhem, Netherlands, Digby prepared his men to use bugle calls if the radios failed. He had a problem with remembering passwords, so Digby, before going to the battle, took an umbrella with him for identification. According to him, if anyone would see him carrying an umbrella into a battle, he would instantly be identified as an Englishman.

He fought the battle wearing a bowler hat, swinging his umbrella in the middle of mortar fire. He even disabled a German armored car poking the driver in an eye with his umbrella. In the same battle, in another instance, he saw the military chaplain pinned down by the bullets of the enemies. Digby simply went to him, opened his umbrella to cover the chaplain and assured him that he was safe from the bullets now. He escorted the chaplain to safety. Later, when one of his fellow soldiers told him that his umbrella would not be of much help, he simply questioned him what if it rained?

Lord Timothy Dexter, an 18th-century American businessman, made idiotic business decisions all his life that oddly paid off. He also once faked his own death and hosted a grand funeral just to see how people would react, then caned his wife for not crying.

Lord Timothy Dexter wasn’t actually a “lord” but an uneducated leather craftsman who was born near Boston in 1748. The title was one he bestowed upon himself to fit amongst the elites after he married a wealthy widow and moved to Boston’s well-to-do Charlestown neighborhood.

Throughout his life, he made strange and idiotic decisions to make a name for himself and to increase his wealth and was oddly successful. In the late 1700s, the Continental dollar, America’s first form of paper money, failed to gain any public trust and so many of the wealthy people tried to do a “good deed” by buying from the public some of the bills. Dexter, thinking it as an opportunity to earn respect, invested all his money and his wife’s money in the now discontinued dollars and bought boatloads of the bills for pennies. Miraculously, the US Constitution was ratified towards the end of the 18th century, and it was decided that the bills could be traded in for treasury bills at 1% of their face values. He became immensely rich instantly.

Later in life when a neighbor tried to bankrupt him by giving him the idea to sell bed-warming pans in the West Indies, he took the advice and voyaged to the West Indies with 42,000 warming pans. There, he realized that the territory enjoys hot weather all the time and there was no demand for warming pans. He rebranded them as ladles and sold them to sugar and molasses plantation owners. The demand was such that he ended up making 79% in profits. Another time, a trader convinced Dexter to sell coals in Newcastle without mentioning that the place already had a large coal mine. Oddly, when Dexter reached the place, the mine was on strike and people flocked to him for coals. He came back with one and a half barrels of silver from there.

He was also a self-published author. His memoir, A Pickle For The Knowing Ones, had no punctuation and was full of errors. It was a complete mess. He didn’t sell the copies of the book but rather gave them away. The demand was so high that a second edition was printed.

One of the most peculiar things he ever did was organizing his own mock funeral. He hired a few trustworthy men to make the arrangements, distributed cards carrying the news of his death. and planned a lavish funeral complete with fancy wines and exotic liquors. His family was to do their part. Three thousand people showed up at his funeral. But when Dexter saw from his hiding place that his wife was smiling, he was enraged. Later, he quietly entered his kitchen and caned his wife, creating a commotion and making the guests enter the kitchen only to find the supposed dead Dexter grinning at them.