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Every party has at least one member who doesn't play by the expected rules. Someone who's got an angle, who has contacts, or who knows just how to lean on somebody. They go by a lot of different names, too. The schemer. The blackguard. The thug. But one of the most applicable titles for them is the scoundrel.
Scoundrels come in a lot of shapes, sizes, races, creeds, and classes. But if you're looking for the kind of background that could have made your scoundrel into who they are today, you might find some of the following options to be of use.
You might also want to check out "10 Backgrounds for Your Martial Characters" over on Improved Initiative if you like this list! And don't forget to check out my Gamers archive for more content like this, while you're at it.
1. The Spy
Every nation in the world, from the great kingdoms to tiny fiefdoms, plays games in the shadows. Games where who finds out whose secrets can be the pebble that starts an avalanche, or which stops a war from ever taking place.
The spy is the one who knows how this game is played.
Whether the character is currently in the trade, or they were simply trained as an operative in their youth, being a spy is more than just a profession. It's a way of looking at the world, and analyzing the situations one finds themselves in. Spies know the value of information, and of decisive, strategic action. Most importantly, they know when not to be seen; a skill that often separates the successful adventurer from the former adventurer.
2. The Soldier
When one thinks of a soldier, they tend to think of rank-and-file men at arms, or of cavalry troops dashing in for a flanking assault. However, those who've held a line are often the ones with the keenest minds, and the least forgiving tactics.
And they know how to get the job done.
From supply sergeants who keep running tallies of who owes who a favor in order to get their hands on the right materials, to elite scouts who can sneak over a line and slit a sentry's throat with no one the wiser, to master tacticians who never do what's expected, armies are positively filled with scoundrels of every sort and description.
Of course, if you were a member of a private army, then chances are good you're an even better fit for the bill. 100 Random Mercenary Companies is a good place to look if you want to find an order you trained with, fought for, or escaped from if you went rogue.
3. The Brigand
The brigand is a predator, preying on the weak and defenseless in order to take what he wants from them. Whether acting as a lone highwaymen waylaying travelers, or someone who is a part of a pack of brutes, the brigand is an expert in the use of force and intimidation.
While many brigands are cowards, much like the great hunters who will back away if they encounter stiff resistance, a good number of them are also daring strategists. Some of them may even offer protection to those they see as vulnerable, choosing to steal only from those they view as greedy, corrupt, or simply wealthy enough to afford the loss.
For those looking for inspiration for a brigand, you may want to check out both 100 Random Bandits to Meet, as well as 100 Random Pirates to Encounter. You can find everything from current and former associates, to captains they may have fought under, to rival gangs they still carry a grudge against.
4. The Noble
Scoundrels are often shaped by the circumstances of their birth; that statement goes both ways, though. While a pauper might ally themselves with a gang to stay safe and to provide for them, one of noble birth may find themselves thrust into a world just as cutthroat as a back alley slum.
Perhaps more so, in many ways.
While the child of a duke, a baron, or a prince may not have to worry about putting clothes on their backs, or food in their bellies, they swim in deadly political waters. One wrong word, one missed courtesy, and they might find themselves (as well as the rest of their family) in dire circumstances. Charm, whispers, and a false face are employed as weapons as surely as any mace... and often with even more dire effect.
Those who can thrive while swimming in these deadly waters often find their skills honed to a razor keenness when it comes to the world outside the salons and private chambers of power. Some become diplomats and power brokers, but others may pretend to be little more than dilettantes in order to hide their true intentions.
For those looking for a place to start, the Crow's Beaks in A Baker's Dozen of Noble Families might be right up your alley.
5. The Treasure Hunter
Stealing from the living is a dangerous profession, but the treasure hunter goes one step further by seeking out lost caches, buried tombs, and forgotten hoards. With the knowledge of a scholar and the wits of a thief, these scoundrels often find themselves matching wits with the long-dead, and the security measures they left behind to guard their wealth after they were gone.
Treasure hunters come in a many different forms. Some of them are world travelers, chasing myths as much as the sheen of gold. Some are learned historians who want to add their name to the history books, and display ancient relics for the world to see. Some are little more than grave robbers, interested only in plunder before anyone else lays their hands on it. They tend to be capable people, though, with unique skills as well as a network of contacts to help them find their treasures, and then to fence the goods once they've been secured.
Some treasure hunters work only for themselves, keeping anything they find. Others may be hired by mysterious benefactors, or operate as agents of an explorer's society, a museum, or even the crown as the rulers seek to find what rightfully belongs in their treasury.
6. The Peacekeeper
While soldiers fight wars, peacekeepers have the more nebulous goal of maintaining order. It's a simple black-and-white matter for some, but for a scoundrel the law is about balance... and getting them closer to their own ends.
The watch lieutenant who cultivates an understanding with the prominent figures of the local underground might turn a blind eye to some things, but in return he expects information, and for certain crimes to be kept well away from his jurisdiction. The tarnished guard might know exactly how far he can push the authority of his badge, while lining his own pockets on the sly. The sheriff's deputy might seem like a genial, naive young man, but he lives a double life under a carefully-constructed second identity in order to track the movements of gangs throughout the territory, find their hideouts, and report back what he's found.
Some scoundrels want to uphold order, even if it means breaking the law. Others uphold the law to enrich themselves and their allies first, and to maintain order second. And sometimes, both types find they have to work together.
7. The Grifter
Trust is a difficult coin to earn, but the grifter is adept at using it. Carefully told lies and perfectly balanced half-truths may look very solid at a glance, but the illusion gives way soon enough. And when it does, the grifter has usually moved on to the next mark.
While grifters come in different forms, the most common trait they share is that they deal in perceptions rather than reality. Some may use magic to influence a person's decisions. Others may dress in finery to convince common people they're noble born in order to receive goods and services they will never pay for, leaving the bills at the doorsteps of the families they impersonate. Whether it's passing off counterfeit treasures, selling properties that don't exist, or convincing the guards they're the revenue agent here to collect the taxes, grifters can be valuable assets when a silver tongue is more viable than a steel blade.
8. The Tradesman
Many scoundrels have a trade; either one they learned earlier in life that they had to leave, or one they've picked up along the way. Given the unique way a scoundrel's mind works, however, this trade is simply another set of skills that can be used to aid them in pursuit of their ultimate goals.
As an example, a mason might use their craft as an excuse to tour a lord's country estate. While he'll make repairs to the walls, he might also leave barely-seen gaps behind so that a knowledgeable person could scale the wall, even in the dead of night. A noted locksmith could ensure that any door or bolt he put in place could be opened by someone who knew the proper trick. A great cook might be shown into the kitchens, where they could lace the evening's meal with a slow-acting drug that would keep the house asleep. Those who wear a uniform, or provide a service, often achieve a strange kind of invisibility.
It is surprising how often a mundane trade can provide openings that scoundrels take advantage of. Especially when they are no longer allowed to freely practice that trade, and must find other ways to make their ends meet. Sailors become pirates, woodsmen turn bandit, and every scoundrel from carpenters, to butchers, to metal workers will find ways to twist their skills into unexpected solutions.
9. The Performer
Like the craftsman, the performer dedicates themselves to mastering a specific set of legitimate skills. Singers, dancers, tumblers, strongmen, archers, axe-throwers, and the list goes on and on. While their skills may make for an entertaining show, it is how these characters use those skills outside of the arena that makes them accomplished scoundrels.
A team of acrobats might be quite engaging when they perform at the duke's estate, however, it's those same skills that allow them to scale the walls unheard and unseen, and to slip in through the skylights to plunder his valuables. The magician's tricks may bring laughs and applause from those in attendance, but those same hands will pluck amulets from throats and rings from fingers without anyone the wiser until long after he's vanished from the castle. Even a talented singer might lull listeners into a trance, while her temporarily deafened cohorts loot the premises.
When art and craft combine, these scoundrels can achieve some impressively audacious feats of skill!
10. The Beast Master
While many scoundrels work with accomplices, there is always a risk that those others will talk if something goes wrong. The beast master, though, recruits helpers who have no interest in gold or jewels, and who can't be made to talk no matter who captures them.
Some beast masters can tap into primal magics in order to call nature to their aid, but others are simply willing to take the time and energy to train their companions. In both cases, though, these scoundrels can make use of beasts' in-born qualities in order to accomplish their tasks.
Burglars might train large lizards to climb walls, and then to brace themselves so the scoundrel can haul themselves up with a rope tied to the lizard's harness. Ravens and crows might carry messages between outlaw bands, sharing information and making the gangs seem nearly omniscient. If you add in the unique powers of magical creatures as well, then a beast master can command a truly frightening amount of power as long as he has the loyalty of his animals.