The 5 Craziest Soldiers of Fortune To Ever Cash a Paycheck

Some people are reluctantly called to war, either drafted into service or volunteering out of a sense of duty. Other people, well, they just really like fighting.

That's why there is such a thing as the soldier of fortune, the mercenary who'll show up and fight in a war between two countries he didn't even know existed until they offered him a paycheck. It takes a certain breed of person to lead this lifestyle. And that breed is batshit insane.

#5. James Long Takes on Texas

You know how sometimes you just get fed up that your government isn't doing something about those bastards across the border? And how sometimes you just go gather your own army and go to war on your government's behalf? No?

Getty
"We have the Second Amendment for a reason. And that reason is going to war whenever we feel like it."

Well, then you're not James Long, a wealthy military surgeon and war veteran. In the early 1800s he settled down in Mississippi, planning nothing more for his future than a quiet, Southern kind of life. Until ...

In 1819, America signed a treaty with Spain that would just let those sons of bitches have Texas! And all the U.S. got in return was freaking Florida. Long could do nothing but sit on his plantation, watching the events unfold and quietly seething in patriotic rage until he just couldn't take it anymore.

narthalc.wikispaces
"What the fuck, arbitrary borderline? I thought we were friends!"

The Madness:

In 1820, Long finally snapped. He gathered several hundred followers and marched straight into Texas. His crew, rumored to be unofficially endorsed by the U.S. government, employed what was perhaps the simplest tactic in military history: They flat out walked in and took over the central town of Nacogdoches. There, they passed the declaration of independence for the newly formed Republic of Texas, elected Long for their president and proceeded to just settle in, establishing their own newspapers and customs rules and everything. While literally in the middle of the legal jurisdiction of a rather powerful and heavily armed European superpower.

texashistorypage
This is a rip-off of something, but we're just not quite sure what.

A month later, the laughter finally died down in Spain and they realized that, holy shit, this Long guy is actually serious. So they sent a 500-strong force to drive him and his followers the hell out of Texas.

Long escaped with his life and whatever dignity he imagined he still had -- and immediately proceeded to raise another army, this time against the freshly independent Mexico that was now in possession of his precious Texas. He managed to gather some 300 men (and his pregnant wife, because whatever could go wrong?), march in Texas yet again and straight up commandeer a Mexican military fort.

Wikipedia
Noted for its excellent pre-natal plan.

Mexico, like Spain before, was getting a bit annoyed by now, so they went in and arrested Long. He was sent to a prison in Mexico City where he was assassinated by a sentry in 1822, presumably while trying to recruit him into his Texas Crusade Mk. III.

texashistory
Meanwhile, his arguably more badass wife and three kids were holding off invaders with cannons.

#4. Neall Ellis Trolls Sierra Leone Rebels to Defeat

Neall Ellis had a successful career as a military pilot behind him and an easygoing civilian life to look forward to. There was just one problem: He was immensely bored with living like a regular guy.

So Ellis decided to become a soldier for hire. Specifically, he started taking work as a private mercenary helicopter pilot, securing his first contract fighting for Bosnia in the Yugoslav wars. After that, he spent some time in Angola. Finally, in the late '90s, his duties took him to Sierra Leone.

BBC
Um, that's probably a welcoming rocket launcher.

The Madness:

The Revolutionary United Front, a rebel faction fighting the UN-supported government of Sierra Leone, was winning in 1999. They were knocking on the door of the nation's capital, Freetown, and the situation was in fact so hopeless that British forces were abandoning the area just as Ellis arrived.

militaryphotos
"The beer's in the fridge. Don't get killed too much!"

Ellis and his team, however, were unshaken by the fact that they were pretty much the only foreigners still in the game. They stayed and fought, presumably for their own amusement, flying missions with Ellis' gunship helicopter and messing with the rebels any way they could. The RUF got so enraged by him that they soon sent him a message:

"If we ever catch you, we'll cut out your heart and eat it."

Ellis responded by stocking his gunship full of weapons (in case he should ever be shot down) and hovering over RUF strongholds, showered them with leaflets saying:

"RUF: This time we've dropped leaflets. Next time it will be a half-inch Gatling machine gun, or 57 mm rockets, or 23 mm guns, or 30 mm grenades, or ALL OF THEM!"

flyafrica
"I'll probably throw myself out, and then you'll be sorry."

After a while, the government of Sierra Leone stopped paying Ellis, because they were forced to abandon the Freetown area, too. Ellis, however, enjoyed the little flame war he got going so much that he kept flying missions for another year, pro bono. During that time, in addition to his usual antics, Ellis single-handedly stopped the RUF from advancing into Freetown -- without a co-pilot, in the middle of the night and without any night vision.

TWICE.

Wikipedia
The first time they forgot the grenades, and everyone knows you get your whole war free if that happens.

At some point, the Brits realized that the ragtag bunch of madmen they'd left behind were actually winning, so they skulked ashamedly back into the fight by financing Ellis and offering assistance.

Ellis and his helicopter stuck with Sierra Leone all the way up to the RUF's defeat in 2002. What does he think of the war-torn country he's spent years fighting in, with a significant portion of its denizens wanting to eat his heart? He loves it. So much, in fact, that he's going to move there when he retires.

flyafrica
"No other country will let me keep my helicopter and my missiles."

#3. Carl Gustav von Rosen and the Biafra Baby Fleet

Some guys just really, really like war.

Take Swedish count Carl Gustav von Rosen. Oh, his career started off normally enough. He started his flying career doing small plane stunts in an aerial circus, then got his first taste of military conflict when Italy invaded Ethiopia in 1936, at which point he apparently said, "I want to do nothing but this, from now on. Find me a war!"

ushmm
Wow, Germany, that's surprisingly generous!

So, when World War II broke out, he immediately volunteered in the Finnish Air Force to combat the Soviet Union. There, he gained notoriety as a bomber -- literally. Unable to score a bomber plane that satisfied his needs, he opted for physically pelting the Soviet troops with bombs, throwing them by hand at the terrified Reds from the open cargo door of a civilian airliner.

guillermodiaz
"Adequate arm room, helpful air-hostesses, effective destruction. Would fly again."

This is when von Rosen started to run out of militaries willing to let him fly for them. He applied to the RAF but was rejected due to his family's Nazi connections. As a backup plan, he went back to flying commercial flights, and after the war became a special UN pilot. After narrowly avoiding death when the United Nations aircraft he was supposed to be piloting was blown up over the Congo, von Rosen decided to take some time off in 1969. And by "time off" we mean he scoured the globe looking for another war to join.

kajgana
For some reason the wars always erupted a few days after he left their protected airspace.

He decided to head to Biafra, to help them in their civil war against Nigeria. Why? Because life just wasn't worth living unless he was flying in an aircraft that other people were shooting at.

The Madness:

Upon arrival, von Rosen noticed some imbalance between the warring parties' aerial capacities. Namely, the Nigerian Air Force consisted of powerful Soviet MiG-17 fighters and large bombers, whereas the Biafran counterpart consisted of paper airplanes that the generals made and threw into the sky.

Wikipedia
The Soviet Nerf-gun 3000.

So he set out to improve their fleet -- the von Rosen way. He bought five of the tiniest, least intimidating planes he could find. Then, he turned these propeller-driven training planes into makeshift war machines by ... well, strapping some rockets onto their wings and giving them a green paint job. That's it, really.

boelkow
The Pimp My Ride of the aviation world.

Still, beggars can't be choosers, and a fleet of tiny, overloaded almost-planes is better than nothing as far as the Biafrans were concerned. So von Rosen was allowed to lead his "Biafran Babies" to battle. And boy, did they kick some serious ass.

Somehow, von Rosen's fleet managed to destroy air bases, troop formations, power plants and a good chunk of the superior-on-paper Nigerian Air Force. Despite being under heavy anti-aircraft fire roughly 100 percent of the time and returning from many of their missions riddled with bullet holes, not one Biafran Baby was ever shot down.

flightglobal
It would be like hitting a mosquito with a house.

Eventually, the Biafrans did lose the war -- but we imagine the old Nigerian war veterans piss themselves to this day whenever they hear the squeaky buzz of a toy plane.

Recommended For Your Pleasure

To turn on reply notifications, click here

371 Comments

The Cracked Podcast

Choosing to "Like" Cracked has no side effects, so what's the worst that could happen?

The Weekly Hit List

Sit back... Relax... We'll do all the work.
Get a weekly update on the best at Cracked. Subscribe now!