You are/were an experienced highwayman with a history of breaking the law. Highway men tend to rely on ambushes, intimidation, and a fast getaway (usually on a horse). Since while most highwaymen hold up travelers and take their money, their exact personality and method vary. Some highwayman kill all of their victims, while others only killing those who fight, and there even those that attempt spare the lives of all of their victims.
- Skill Proficiencies: Choose two from Deception, Stealth, Animal Handling, or Intimidation.
- Tool Proficiencies: Choose two from: a type of gaming set, thieves’ tools, or vehicles (land)
- Equipment: A crowbar, a set of dark traveler's clothes including a hood or a set of fine clothes, a scarf or bandanna that functions as a make shift mask, a hammer to break locks, and a pouch containing 15 gp.
There are many methods of robbery and personality for a highwayman.
Gentleman, try to appear as noble as they can. They wear fine clothing and the best weapons they can.
Raiders, ambush their victims on the road (wearing simpler and less expensive clothing).
Inside Agents, travel with their victims before attacking them (either in their sleep, with a partner, or just at an opportune moment).
Stalkers, track their victims, waiting for an opportune moment to strike.
Actors, attempt to convince their targets to stop (and ideally lower their guard) either by pretending to be in distress OR by just being in the way.
Footpads, always operate on foot and rob people by putting them in fear often by hiding in darkness (which also allowed them more easily escape and diminishes the chance of recrecognition).
| d6 | Robbery Personality |
|---|---|
| 1 | Gentleman |
| 2 | Raider |
| 3 | Inside Agent |
| 4 | Stalker |
| 5 | Actor |
| 6 | Footpad |
Highwaymen wander the roads or lie in wait looking for victims, leading many to have a Trusted Contact to whom they can fence their purloined goods to. Your contact may also be a liaison to a network of other criminals. You know how to get messages to and from your contact, even over great distances; specifically, you know the local messengers, corrupt caravan masters, and seedy sailors who can deliver messages for you. [Note: This is a modification/reflavoring of the Criminal Contact feature.]
Suggested Characteristics
Highwaymen might seem like villains on the surface, and many of them are villainous to the core. But some have an abundance of endearing, if not redeeming, characteristics. There might be honor among thieves, but criminals rarely show any respect for law or authority.
| d8 | Personality Trait |
|---|---|
| 1 | I always have a plan for what to do when things go wrong. |
| 2 | I am always calm, no matter what the situation. I never raise my voice or let my emotions control me. |
| 3 | I am patient. I am willing to wait for long periods of time to get what I want. |
| 4 | I am incredibly slow to trust. Those who seem the fairest often have the most to hide. |
| 5 | I don't steal those who can't afford to be stolen from. |
| 6 | I don’t pay attention to the risks in a situation. Never tell me the odds. |
| 7 | I Never turn my back on anyone whether they be friend or foe. |
| 8 | My gang/group is my family, and I will do anything I can to help them. |
| d8 | Ideal |
|---|---|
| 1 | Honor. I never steal from others in my trade. (Lawful) |
| 2 | Respect. I never harm those who do not pose a threat to me and I am always polite, even to those I am robbing. (Lawful) |
| 3 | Charity. I steal from the wealthy so that I can help people in need. (Good) |
| 4 | Freedom. Chains are meant to be broken, as are those who would forge them. (Chaotic) (WILL CHANGE) |
| 5 | People. I’m loyal to my friends, not to any ideals, and everyone else can take a trip down the Styx for all I care. (Neutral) |
| 6 | Greed. I will do whatever it takes to become wealthy. (Evil) |
| 7 | Infamous. If I can't be Famous, I will be Infamous. (Evil) |
| 8 | Independence. I am a free spirit – no one tells me what to do. (Chaotic) |
| d8 | Bond |
|---|---|
| 1 | I’m trying to pay off a(n) (old) debt to someone. |
| 2 | Most, if not all, of my ill-gotten gains go to support my family. |
| 3 | I have somebody for who, I will, do anything they ask of me. |
| 4 | Something important was taken from me, and I aim to. Get. It. Back. |
| 5 | I will become the greatest highwayman that ever lived. |
| 6 | I've killed an innocent during a botched robbery, I don't think I'll ever forgive myself. |
| 7 | Someone I loved died because of a mistake I made. That will never happen again. |
| 8 | I am a sucker for a pretty face. |
| d8 | Flaw |
|---|---|
| 1 | If a person draws a weapon on me, I will not hesitate to kill them. |
| 2 | When faced with a choice between money and my friends, I usually choose the money. |
| 3 | I love robbery. I love the power/thrill/control/sucess that I have when I do it. |
| 4 | I have an addiction. |
| 5 | I turn tail and run when things look bad. |
| 6 | An innocent person is in prison for a crime that I committed. I’m okay with that. |
| 7 | It takes a lot to actually earn my trust. |
| 8 | I'm too greedy for my own good. I can't resist taking a risk if there's money involved. |
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