The internet has opened new doors for many, providing fresh ways to learn, earn, and communicate. However, like many emerging technologies, it hasn't come without its risks. One of the unforeseen consequences was the rise of 'internet trolls'—individuals who seek to embarrass or fool others by making inflammatory remarks or spreading deception.
Despite its close association with the digital world today, trolling isn't a recent phenomenon. In fact, it dates back centuries, having been utilized in politics, warfare, art, and comedy. Several notable figures throughout history have fallen victim to trolling, and some have even engaged in it themselves. Here are ten of the most astonishing and unexpected instances of trolling that took place before the internet existed.
10. The Birth of Trolling

Why do we refer to these instigators as 'trolls'? In folklore and fantasy, trolls are typically not seen as benevolent beings, though, as in life, things aren’t always what they seem. Interestingly, the term 'trolling' wasn't inspired by these mythical creatures. Instead, the name originates from an ancient fishing technique known as 'trolling.'
The term 'trolling' originally referred to the act of casting bait on a hook into the water. Instead of waiting for a fish to bite naturally, trolling involves slowly dragging the bait through the water, making it appear as though it is alive and swimming. This method is deceptive, much like the 'bait' trolls use. They make exaggerated or false statements, often ones they don't truly believe, with the goal of provoking a reaction. Typically, this response is designed to make the target feel embarrassed or uncomfortable.
Unlike fishing, which has a singular goal, trolling can serve multiple purposes. For some, it's a harmless joke, but for others, the motivations are far darker, with more malicious intentions at play.
9. The Littlehampton Letters

In 2023, the movie *Wicked Little Letters* brought to life a true story from a quaint seaside town in England. An anonymous troublemaker in Littlehampton, West Sussex, launched a series of vulgar and abusive letters targeting some of the town’s most respected citizens. Among the insults, they infamously claimed that someone’s homemade cakes were created using the rear end of a sheep, though the language used was far more explicit.
While swearing is commonplace on social media today, what’s truly shocking is that this happened in the 1920s. The scandal was so enormous that it made national headlines and even sparked debates in Parliament. The letters, first received by Edith Swan, were thought to be from a disgruntled neighbor, Rose Gooding. Soon, more townsfolk began receiving similar letters, leading to Rose’s imprisonment twice, despite little evidence to implicate her.
Ultimately, Edith was uncovered as the culprit and convicted. After being spotted tossing one of the letters at someone’s house, a police operation caught her in the act at the post office with another letter in hand.
8. Diogenes of Sinope

Diogenes of Sinope, also known as Diogenes the Cynic, serves as an early example of someone who could easily be seen as a precursor to modern trolls. This philosopher, who lived in a barrel on the streets of Corinth during the 4th century BC, became one of the era's most renowned figures. However, it’s probably a good thing that he didn't have access to the internet.
Diogenes was notorious for his provocative and often offensive behavior, which ranged from loudly eating and disrupting Plato's lectures to spitting at people and exposing himself. One of his more insightful stunts involved walking the streets during the day with a lantern, declaring that he was 'looking for an honest man' when questioned about his actions.
Interestingly, when asked to name the most beautiful thing in the world, Diogenes famously responded with 'freedom of speech'—a concept that internet trolls today might use to justify their behavior.
7. Niccolò Machiavelli

Political trolling, often seen on the internet today, has deep historical roots. The tactics used to undermine political enemies and their supporters, making them appear foolish, unlikable, or weak, likely began the moment power structures were formed. Niccolò Machiavelli, in his influential work *The Prince*, outlined many of these manipulative strategies for gaining and maintaining power.
However, some believe that *The Prince* itself was a clever ruse to strip Lorenzo de’ Medici of his authority. While the advice within the book appeared practical and reasonable, it is thought that Machiavelli's recommendations were actually meant to incite animosity toward the ruler. English Cardinal Reginald Pole, after learning that one of King Henry VIII’s most ruthless advisors had read the book, investigated it himself.
In Florence, Pole uncovered that some of Machiavelli's writings were, in his own words, designed more to please a prince than to offer genuine counsel. Pole concluded that the book was 'like a drug that causes princes to go mad.' Additionally, Machiavelli had personal reasons for wanting to bring down the Medici family, as they had previously dismissed him from his position and had him imprisoned and tortured.
6. King Louis XVI and Marie Antoinette

Trolling can figuratively lead to someone 'losing their head,' but in the court of King Louis XVI of France, it might have literally helped a few heads roll. The Comte de Provence and the Comte de Artois, both brothers of the king, were envious of his power and spread malicious rumors throughout the palace about him and Marie Antoinette.
They spread rumors about their brother’s lack of bedroom skills, claiming it led to the queen’s affair with Artois. When Louis and Marie's first child, Princess Marie-Thérèse, was born in 1778, the Comte de Provence fueled doubts about the child's true parentage.
Posing as a concerned observer of royal procedure, he pointed out during the child’s baptism that the “name and quality” of her parents had not been officially stated. Such rumors contributed to the growing unpopularity of the French monarchy, which eventually led to a public revolt against them.
5. Napoleon

A person with an aggressive demeanor and a short stature is often said to have a 'Napoleon complex,' a term inspired by the famously short French emperor. However, at 5’7″, Napoleon was only slightly shorter than the average French man of his time, and in fact, taller than many of his contemporaries.
The belief that Napoleon was short largely stems from British wartime propaganda designed to provoke him. His enemies knew that mocking his height would irritate him, so they made it a central theme in cartoons and pamphlets, even during peacetime. Napoleon even instructed his diplomats to ask the British to censor their press, seeing the campaign as a 'deliberate provocation.'
Naturally, his request was ignored, only proving that the propaganda was succeeding in getting under his skin. As a result, the trolling continued. After his defeat at Waterloo and subsequent exile, Napoleon allegedly remarked that British political cartoonist James Gillray 'did more than all the armies of Europe to bring me down.'
4. Ian Fleming and Operation Mincemeat

Misinformation is a common tool for trolls, but before the age of computers and manipulated images, the methods were more creative. One of the most imaginative examples of this came from a man who would later create one of the world's most iconic fictional characters. That man was Ian Fleming, the author of James Bond, whose daring deception even managed to fool Hitler himself.
Fleming masterminded Operation Mincemeat, a plan to convince the Axis powers that the Allies were preparing to invade Greece, when the true target was Sicily. The operation involved dressing the body of a dead homeless man as a British military courier, then dumping it in the sea off the coast of Spain, which was teeming with Nazi spies. The body carried a letter marked 'PERSONAL AND MOST SECRET,' detailing the fabricated invasion plans for Greece.
The process of making the body and documents appear authentic took several months, but the effort paid off. The fake plans made their way up to Hitler, who was convinced of their legitimacy and moved 90,000 soldiers to Greece. This diversion allowed the Allies to successfully invade Sicily, overthrow Mussolini, and gain the upper hand against the Germans.
3. Haydn’s Musical Joke

Classical music is often associated with formality, but many composers, including the 18th-century Austrian Joseph Haydn, composed playful and witty pieces. Haydn’s string quartet *Opus 33 Number 2*, subtitled 'The Joke,' contains one of his most famous musical pranks and can definitely be seen as a form of trolling.
In this piece, Haydn employs long pauses and a false ending, tricking the audience into clapping prematurely. He repeats this multiple times, each time leading them to believe the piece has ended, only to continue. Finally, the music ends abruptly in the middle of a phrase, creating the impression that it was supposed to continue.
This sequence of musical misdirections isn’t necessarily intended to provoke laughter, but it has succeeded in confusing audiences for centuries.
2. Merde d’Artiste

The realm of avant-garde art often appears to outsiders as a space where serious individuals admire outlandish works created by equally serious artists, with significant amounts of money exchanged. Piero Manzoni, an Italian artist, viewed this world as somewhat absurd. He believed that contemporary art audiences were so naive they would purchase anything simply because it bore the signature of an artist.
In 1961, Manzoni decided to test this theory by pulling off an audacious stunt. He filled 90 cans with his own “freshly preserved, produced, and tinned” feces and sold them at the same price as gold. To his astonishment, they sold. Over the years, these tins have fetched sums of money in the thousands.
But Manzoni's trolling didn't stop there. In 2007, it was revealed by a collaborator that the cans did not contain the 'Merde d’artiste' as claimed, but instead were filled with plaster.
1. George Washington

Trolling historical figures wasn't exclusive to wartime. For instance, George Washington became the target of a media campaign orchestrated by his fellow countryman during his post-Revolution presidency. Benjamin Franklin Bache, the publisher of a newspaper, took aim at Washington by criticizing him and spreading libelous accusations. These accusations, often rooted in Washington’s political rivals, were not necessarily concerned with truth, but rather with Bache's agenda.
Bache felt slighted that Washington didn’t grant him and other members of prominent families the influence and status they believed they deserved. In retaliation, he took every opportunity to attack the first president. When Washington refrained from taking sides during the French Revolution, it was to protect the fledgling nation’s image. However, Bache accused him of betraying a key ally.
When Washington signed the Jay Treaty, seeking to avoid further conflicts with Britain, Bache stoked anti-British sentiments. He resorted to dishonesty, even publishing forged documents to tarnish the president's reputation.