Satirical writing would probably be the best example of "trolling" as some people would take the writing seriously.

But trolling is a pretty nebulous term. Hard to define. Part of the troll is fooling people into thinking you've told them a truth, but you're actually telling them a lie. So does intent matter? If the intent isn't to fool people, but people get fooled anyway, is that a troll?

One could argue that another form of trolling is acting purposely outrageous to generate controversy. Your modern "celebrity" often does this. And if you look at people like Oscar Wilde, you can see that this behavior wasn't unknown in the past. Are there older examples? It's possible, but I don't have my eyeglasses with me so I can't name names.

But I'll say this. Trolling is only possible when someone has enough status to be heard but can't lose that status no matter how ridiculous they act. The peasant can't troll the nobility or their head gets chopped off. So when looking for history's greatest trolls, you have to keep that in mind! Good luck, guys!

Edward Abbey worked for the National Park Service through the 1960s. And while he would later become known for his environmental writings with non-fiction pieces likeDesert Solitaire and fictional pieces including The Monkey Wrench Gang, this time working in the parks featured bits of activism that I feel can only be defined as trolling.

So the guy is an outspoken critic of public land policies in a time where the government is building a bunch of highways and access roads so that people can see the environment oddly enough.

Abbey, being, in essence, a lone mountain ranger, comes across these road crews and their surveyors more than once. The surveyors would leave stakes and other markers in place so that the crews could lay down the pavement. Abbey decides otherwise and simply take the markers down/pulls the stakes out on more than one occasion. A lower grade form of Abbey's larger idea of eco-sabotage for sure.

These shenanigans were described in Roderick Frazier Nash's Wilderness in the American Mind, 4th edition (if I recall correctly, I currently do not have my copy available)

The English satirist Johnathan Swift (famous for Gulliver's Travels) definitely qualifies. He wrote A Modest Proposal, in which he proposes that impoverished Irishmen sell their children as food for wealthy Englishmen.

He's also known for his feud with John Partridge, who published an almanac in which he predicted the deaths of several church officials. Swift published his own almanac under the pseudonym Isaac Bickerstaff predicting Partridge's death. He then followed up on this by publishing a pamphlet on the day of Partridge's predicted death claiming that he had actually died. Partridge reportedly had trouble convincing people he was actually alive for the rest of his life.

Graffiti in public places has been found dating to classical times, which would have enjoyed the same anonymity as internet trolls.

The original War of the Worlds radio broadcast in 1938 certainly trolled a lot of people into believing Earth was under invasion.

Ken Kesey's Merry Pranksters in the 1960's were celebrated trolls. They'd make official-looking signs with messages like 'No Spitting', and put them up in tony restaurants.

Dadaist art like Duchamp's Fountain, 1917 trolled the art world to scandalous effect.