Just as the world of doctors is divided into many types — pediatricians and cardiologists and surgeons and otorhinolaryngologists — so too is the world of thieves.
Which makes sense, when you stop to think about it. The skills needed to be a good pickpocket are not the skills needed to be a good housebreaker. The latter needs to be able to pick locks and maybe climb walls; the former needs to pass unnoticed in crowds and get their hand into a pocket so delicately the target hopefully doesn’t even notice the loss until much later. Experienced cattle rustlers may be innocent country mice in a city, while jewel thieves are helpless city mice out in the countryside.
These particularized skills apply to more than just the act of theft itself. How do you know what’s a good target, versus one that’s insufficiently profitable or far too dangerous to be worth the risk? Will you be treading on another thief’s turf if you go after a particular mark? And once you have your ill-gotten gains in hand, where can you unload them? Books on historical English underworlds record a bewildering array of specialists: anglers, curbers, or hookers stole by means of a stick with a hook at one end which they could slide through an open window, while lumpers worked unloading ships, slipping items into the pockets of their baggy coats as they went. One Regency-era fence dealt only in stolen handkerchiefs; another paid primarily for things like brushes, pails, and coal scuttles.
But two particular specialties deserve individualized attention, first because necessity forced them to operate in different ways, and second because of the glamour that has attached to their names. The specialties in question? Pirates and highwaymen.
Neither of those is a job you can really do on your own. In the case of pirates, you obviously need a crew to sail the ship and man the guns. While there are solo craft, good luck catching up to a rich merchant ship on your own, much less overwhelming her crew or intimidating them into surrender. Making a living as a pirate requires finding the ideal balance between enough people to get the job done, but not so many as to dilute the profits beyond use.
But the same, less obviously, is true of highwaymen. True, you only need a horse and not an entire ship . . . but if you want to target more than a single rider, it helps to have help. Heck, even if you are going after just one person, you’re better off with a partner who can help flank the victim and keep them from trying anything foolish. The people with real wealth, though, are usually going to be traveling in carriages, with at least an armed coachman to protect them. And the truly plump birds are going to be the carts bearing things like strongboxes stuffed with taxes or a merchant’s profits. Those don’t tend to travel without their own halo of guards.
So although we tend to remember the names of the famous individuals — the Blackbeards and Dick Turpins of history — they were rarely solo actors. Behind and alongside them were groups of (usually) men, without whose assistance very little would have been accomplished.
Why are these types of criminals romanticized? To begin with, unlike most thieves, their work involves direct encounters with their victims. An angler hopes nobody notices her hooking their property out of a window; a pickpocket does his level best to blend into the crowd, and bolts if he’s noticed. Their names only become well-known when they come under suspicion by the police or are brought up on charges. But pirates and highwaymen openly confront their targets — and more often than you might think, those targets live to tell the tale. After all, even when larceny is a capital crime, the authorities will pour a lot more energy into pursuing gangs that make a habit of committing mass murder along the way. The general populace doesn’t like it as much, either, which reduces the number of places the gang can find refuge. So while deaths certainly did happen, enough people survived these encounters to spread tales of those who’d robbed them.
There’s also the matter of who gets robbed. If your neighbor’s coal scuttle gets stolen from her back step or her apron gets yanked off a laundry line, you’re probably going to be annoyed on her behalf. But a big gang needs big profits, and so pirates and highwaymen are going to preferentially target fat pigeons: the ships and wagons belonging to merchants, aristocrats, and the government. When gross economic inequality is the norm, it’s not surprising to see the common people cheering on anyone who can take the elites down a peg. This, of course, is the Robin Hood legend, in that case with the added glitz of Robin giving the proceeds to the poor. (Sorry to break it to you, but very few thieves have ever been that noble-hearted.)
Even beyond those factors, though, there’s a certain social glamour to both such trades. In societies where most people lived fairly constrained lives, both the pirate and the highwayman roamed as free as the wind. Of course it often wasn’t as pleasant as it sounds; they spent a lot of time sleeping rough or otherwise enduring the elements, and when pickings were lean or they had to lie low to avoid pursuers, they might go just as hungry as the average subsistence farmer. But songs and tales leave those details out, focusing instead on the romance of freedom.
And in their own way, these kinds of thieves form an elite. If you robbed people along the highway without a horse to your name, you were just a footpad, which in the criminal underworld was very much inferior. Highwaymen, with their expensive mounts, were euphemistically referred to as gentlemen of the road or knights of the road, even when their birth was common. For pirates, not only are ships also valuable assets, but there’s a significant crossover with privateering, i.e. government-sanctioned piracy as part of a war. No few pirates started out as privateers, then kept going when their official commission was rescinded. The heroic aura of sticking it to the enemy can remain.
Finally, of course, there’s the hazy softening of time. Unquestionably there were contemporary broadsheet ballads and folktales glamourizing the deeds of such crews, but I don’t think those are a patch on what you see today. Modern representations of the golden age of piracy or highway robbery make the instigators out to be dashing gentlemen, flirting with the ladies and tossing off a few quips before heading out with the loot, leaving their victims unharmed except for a brief scare. We significantly elide the violence involved, the psychological scars it leaves behind.
Highway robbery has declined sharply in modern times, I suspect due to the difficulties inherent in hijacking motor vehicles. (Despite what the Fast and the Furious franchise wants you to believe. Though train robbers in the American West? Highwaymen operating under different conditions.) Piracy, however, definitely still exists today. In 2009 the Maersk Alabama made headlines when a group of pirates hijacked it; the incident became a film starring Tom Hanks. But in contrast with the valorizing depictions of historical piracy, Hanks plays the captain of the hijacked ship, not the captain of the pirates. The latter were a group of Somali men, striking against a U.S. ship.
We’re the elites now, the fat pigeons being targeted by an impoverished underclass. And it doesn’t seem nearly as romantic when we’re on this side of the equation.