Top 10 Strangest Deaths in the Middle Ages

You may have heard how medieval rulers have been killed in battle or by an assassin’s blade. But did you know about the king who died from uncontrollable laughter or the emperor who was dragged 16 miles through a forest by a deer? Check out our list of the top ten strangest deaths from the Middle Ages!

Falling out of the Tower of London

Gruffudd ap Llywelyn ap Iorwerth was a Welsh prince who had spent much of his life in captivity – either held by his own family or by the kings of England as a hostage. In 1244, Gruffudd was being held at the Tower of London, although with benefits such as having his wife allowed to visit him. However, he decided he wanted to escape. The English chronicler Matthew Paris explains what happened next:


One night, then, having deceived his gaolers, and made a cord out of his sheets, tapestries, and tablecloths, he let himself down perpendicularly by means of the same rope from the top of the Tower. And when he had thus descended some distance, from the weight of his body, the cord snapped, and he fell from a great height; for he was a big man, and very corpulent; and in this way he broke his neck, and died; and his pitiable corpse was found in the morning near the wall of the Tower, and afforded a lamentable spectacle to all who saw it, as his head, together with his neck, was almost buried in his breast between the shoulders.

Gruffudd’s fall from the Tower of London – British Library MS Royal 14 C VII f. 136r

The Fly

Pope Adrian IV is known as the only Englishman to serve as Pontiff. His papacy came to an end in 1159 while he was suffering from tonsillitis that had caused puss to build up in his mouth. According to one account, he took a sip of wine and began to choke on a fly, which had been floating inside his goblet. Combined with the puss in his throat, the Pontiff died within minutes.


Road accident

King Louis VI of France adored his son Philip, even naming him co-King in 1129. However, several chronicles did not share the king’s lofty opinion, complaining that the teenaged Philip was brash, arrogant and disobedient. Then two years later, this happened, according to Louis’ biographer Abbot Suger:

he was riding through a suburb of the city of Paris one day when his horse stumbled over a diabolical pig that it bumped into on the road. Taking a very bad fall, the horse threw the noble youth riding it against a stone and crushed him underfoot with all his weight. 

Philip’s death – British Library, MS Royal 16 G VI f. 309r

Another chronicler, Walter Map, offers a different version, where Philip seems to be a victim of joy-riding:

one day when, in the company of many knights, he had put his horse to the gallop in the part of Paris which is called La Greve, a black pig rushed out of a dunghill on the bank of the Seine, and ran in among the feet of the galloping horse. The horse stumbled and fell, and the rider broke his neck and died; but the pig plunged into the Seine, and as no one had seen it before, so it was seen of none afterwards. 


Poisoning Oneself

Baybars al-Bunduqdari, the Mamluk ruler of Egypt and Syria, was a ruler known for his ruthless determination to hold onto power. He used a network of spies to keep him aware of threats, both external and internal, and gained much success against the Mongols and Crusaders. However, in 1277 Baybars’ astrologers warned him that a king would soon die of poison. The sultan had just returned from a campaign in Anatolia where an Ayyubid prince had performed very well. This made Baybars jealous, and he believed that if the prince died, it would fulfill the prophecy.

Baybars invited the prince to a banquet in Damascus, and during the festivities, the Sultan put a deadly poison into his own goblet and then offered it to the prince to drink. The Ayyubid prince did so – his fate was sealed. Then Baybars left the banquet for a few minutes – as this happened, one of his servants took the goblet from the prince and refilled it. When Baybars returned, the servant offered him the same goblet and the sultan had a drink –  there still was a trace of the poison in the cup.

The Ayyubid prince would die that night, but Baybars would suffer in agony for several days before he passed away – thus fulfilling the prophecy.


A Dead Man’s Revenge

Sigurd Eysteinsson was a ninth-century Earl of Orkney and had gained the nickname Sigurd the Powerful. He went to war with Máel Brigte of Moray and, according to the Orkneyinga saga, both sides agreed to do battle with just forty men. However, Sigurd changed his mind and brought 80 men, which allowed him to win the battle and kill Máel and his forces. The saga records what happened next:

Sigurd had their heads strapped to the victors’ saddles to make a show of his triumph, and with that they began riding home, flushed with their success. On the way, as Sigurd went to spur his horse, he struck his calf against a tooth sticking out of Máel Brigte’s mouth and it gave him a scratch. The wound began to swell and ache, and it was this that led to the death of Sigurd the Powerful.

Máel Brigte himself gained a new nickname posthumously: ‘The Bucktoothed’.

Combination Fall and Dwarf

Henry II, Count of Champagne, had become the King of Jerusalem in 1192, although he was reigning over a much-diminished kingdom in the wake of the Third Crusade. His own reign  came to an end in 1197: he was watching his troops gather from his palace in Acre when, in the words of one chronicler:

He was leaning on the railings of a window and looking down. The railings gave way, and he fell to the ground. His dwarf, frightened and distressed, fell out too and landed on top of him. It was said that if the dwarf had not fallen on him he would perhaps not have died so soon.


A slightly different version has Henry at the window when envoys from Pisa arrived – as the count turned around to greet them he fell backwards. His dwarf servant, named Scarlet, tried to grab his sleeve but was pulled out too. Henry was killed immediately, while the servant died later of a broken leg.

Being dragged for 16 miles

The Byzantine Emperor Basil I (867-886) spent the last few years of his reign worrying about plots to overthrow, even from his own family. However, it was a hunting accident that would end his rule and life. According to the Vita Euthymii, the Emperor was in Thrace hunting dear along with his entourage:

He was giving chase alone, for his companions were tired; but the stag, seeing him isolated, turned in his flight, and charged, trying to gore him; he threw his spear, but the stag’s antlers were in the way, and it glanced off useless to the ground. The emperor now, finding himself helpless, took to flight; but the deer, pursuing, struck at him with its antlers, with the result that it carried him off. For the tips of the antlers having slipped under his belt, the stag lifted him from his horse and bore him away, and no one knew this had happened, till they saw the horse riderless. 

His followers soon began to search for the emperor, and soon one man was able find Basil and free him by cutting off the belt. However, once Basil regained his senses, he accused the man who had just saved him of trying to kill him and ordered his execution.

The Byzantine emperor Basil I (left) with his son Leo VI

Basil wanted to learn how far the deer dragged him, so his officials measured it and found it was sixteen miles! The emperor seems to have suffered from internal bleeding, and nine days after the hunting accident he died.

The Erfurt Latrine Disaster

One should not be surprised that building codes were not a thing in the Middle Ages, so deadly collapses could happen. This was the case on 26 July 1184 at Erfurt, Germany – a meeting was being held by Henry VI, King of the Germans, to settle various local disputes and dozes of nobles were in attendance. However, the meeting was being held on the second floor of a building and partway through the wood floor gave way. Even worse, below was a latrine, and in the words of one chronicler, “many fell into the cesspool below, some of which were rescued with difficulty, while others suffocated in the morass.”

Another account noted that 60 people died, either crushed by the debris or drowned in the latrine. Meanwhile, King Henry and his attendants were luckily standing at a window embrasure and did not fall in, although they had to cling to a frame until they were rescued by a ladder.

Death by Malmsey Wine

George Plantagenet, Duke of Clarence, was the brother of England’s King Edward IV, but he often proved to be a hindrance to his royal sibling. Geroge had on more than one occasion joined plots against the king, and in 1477 had organized the execution of two people he had erratically suspected to have poisoned his late wife. The frustrated king ordered his brother’s arrest and execution, which took place on 18 February 1478 at the Tower of London.

A 16th-century portrait of George Plantagenet, Duke of Clarence

We do not know how George was killed, but very soon after his death a rumour emerged that he was drowned in a large vat of Malmsey Wine, and that George had asked for this form of execution, as it was his favourite beverage.

Death by laughing

Martin the Humane, King of Aragon and Sicily, died in 1410, and we have several versions of how he died, including that he was poisoned or suffered complications from severe obesity. Another story has Martin just having eaten an entire goose when his jester entered the king’s bedroom. Martin asked him where he had been, and the jester replied “Out of the next vineyard, where I saw a young deer hanging by his tail from a tree, as if someone had so punished him for stealing figs.” The king found this so funny that he began laughing uncontrollably until he fell over and died.