The world is full of people who have insane stories to tell, and this has always been the case. Every century had its own share of people who were absolute crazies or were able to blur the line between bravery and insanity or led such eccentric lives that decades and centuries after them, people still keep discussing their lives. This list is about such 10 crazy people in history and their bizarre stories.

1 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. (source)

2 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? (source)

3 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. (source)