Romanticising Rebels: Why We Love Outlaws

Pirates and Che Guevara - JAMIE WILMOT explores the reality behind our most iconic and commodified renegades

Picture this - a pirate ship, its black flag snapping in the wind as it bears down on a merchant vessel.

Now jump forward a few centuries - a ragged band of guerrillas, led by a man with a beret and a rifle, moves through the jungle.

One ruled the high seas, the other fought in the mountains.

One lived for gold; the other died for an idea.

Pirates and Che Guevara - two of history’s most romanticized rebels. We put them on T-shirts, quote them in Instagram bios, and turn their lives into adventure stories. But behind the legends, both were violent, complicated figures. So why do we keep turning them into heroes? Maybe because everyone loves an underdog. Or maybe because rebellion - whether against kings or empires - always makes for a good story

Why We Can’t Resist a Good Outlaw

From Robin Hood to Darth Vader (before the redemption arc of course), humans have always been drawn to rebels. There’s something thrilling about someone who flips off the rules - especially when the rules are unfair.

Pirates, for all their plundering, were seen as anti-establishment. Many were ex-sailors who’d been screwed over by the British Empire - low pay, brutal captains, and rotten food. So, they mutinied, formed their own crews, and made up their own rules. Some pirate ships were shockingly democratic: Captains were elected, loot was shared, and decisions were made by vote. (Take that, 18th-century monarchy!).

Che Guevara, meanwhile, was a middle-class doctor who ditched a comfortable life to fight revolutions across Latin America. He wasn’t just rebelling - he wanted to burn the whole system down. And like pirates, he became a symbol of defiance.

But here’s the catch. We forget the ugly parts. Pirates tortured prisoners. Che executed traitors without trial. Does their cause excuse their cruelty? Or do we just ignore the blood because the story is so damn compelling?

Shock Tactics and Psychological Warfare

Pirates didn’t win battles by being nice. They won by being terrifying.

Before attacking, they’d raise the Jolly Roger - a skull and crossbones meant to make their victims surrender without a fight. Why risk a battle when fear could do the job for you?

Che Guevara did the same thing - just with rifles instead of cutlasses. Guerrilla warfare is all about striking fast, disappearing, and making the enemy paranoid. Che’s rebels in Cuba were outnumbered, so they relied on ambushes, propaganda, and sheer audacity (this all happened from 1953-59).

Both pirates and guerrillas understood something crucial - if you can control the story, you don’t always need to win every fight.

Rebels With (Very) Different Causes

Here’s where things get messy.

Pirates were in it for themselves. Sure, some crews split treasure fairly, but at the end of the day, they wanted gold, rum, and a good time. They weren’t trying to build a new society - they just didn’t want to be part of the old one.

Che Guevara, on the other hand, was a true believer. He didn’t just hate capitalism; he wanted to replace it with something he thought was better. Whether it actually was better is a whole other debate.

So, while both were rebels, their endgames were totally different:

• Pirates: "Screw the system, let’s get rich."

• Che: "Screw the system, let’s rebuild it."

Which is more admirable? The selfish rogue or the self-righteous revolutionary?

How Capitalism Swallowed the Revolution (And Sold It Back to Us)

Here’s the ultimate irony - both pirates and Che Guevara have been turned into brands.

Pirates, once the scourge of empires, are now lovable rogues in Disney movies. We dress up as them for Halloween, ignoring the fact that real pirates were more like violent thieves than Johnny Depp.

Che Guevara’s face, meanwhile, is plastered on T-shirts, coffee mugs, and even NFTs - despite the fact that he’d probably have hated everyone buying them. His image, stripped of its meaning, has become shorthand for "cool rebellion."

So, what does it say about us that we’ve turned anti-capitalist icons into capitalist products? That rebellion is just another trend? Or that even the most radical ideas get neutered by time and consumerism?

Hackers, Hacktivists, and the New Pirate Code

Pirates didn’t disappear—they just went digital.

Today’s rebels aren’t swinging cutlasses; they’re writing code.

Groups like Anonymous and WikiLeaks steal secrets instead of gold, but they’re still fighting powerful empires (just now, it’s governments and corporations).

Some, like Edward Snowden, even see themselves as modern-day Che Guevaras - whistle-blowers sacrificing everything for a cause. Others, like cryptocurrency anarchists, want to smash the system just like pirates did.

But are today’s rebels any different? Or is rebellion just part of the human script - always changing costumes, but never really changing the game?

The Problem With Heroic Rebels

We love rebels because they promise something rare - the chance to fight back and win.

But the truth is messier. Real rebellion isn’t a movie. It’s not always noble. Sometimes it’s selfish. Sometimes it’s brutal. And sometimes, even when it wins, it just becomes the new thing to rebel against.

So next time you see a Che Guevara poster or a pirate flag, ask yourself:

• What’s the real story behind the symbol?

• What’s being left out?

• And would I actually want to live in a world run by these rebels?

Because history’s outlaws are never as simple as the legends make them seem.

Written by JAMIE WILMOT (English Literature student, University of Chester, UK)