You know well the hazards of the road, you happen to be among the worst of them. Long have you made your living on the unfortunate souls who crossed your territory and caught your eye. Merchants, caravans, adventuring parties, it mattered not who they were, where they were going, or what it was they intended to achieve, what mattered was that you needed coin to survive and they had it to spare.
A highwayman (or highwaywoman) is like a bandit, but with standards and a bit better chances of evading capture. Never hit a mark that's lower on their luck than you. Never target someone that is more trouble than they're worth. Never stay in one place for too long. You have learned to survive on the spoils of the land, and to end a fight before it begins. Killing everyone you cross sounds great on paper, but gets you locked up a hell of a lot quicker. It's best to catch and release when and where possible. Never make them fight, always give them an out. Sure, you might not get their whole haul, they gotta live to make it to the next town after all, but you get their valuables, and a living is made.
Further, through your extensive scouting of various regions, you have managed to mark out a cache of unclaimed goods of value and a map to them. Roll this on the Highwayman's Cache table, and confer with your DM about the exact nature of this. This cache will serve as a quest for yourself and your party, and will be left to the DM as to what, exactly, the quest will entail.
- Skill Proficiencies: As a raider of the highways and roads, you gain proficiency in two of Animal Handling, Intimidation, Survival, or Stealth.
- Tool Proficiencies: You gain proficiency in one tool useable in the wilds. Every member of your camp needed to carry their weight, you were no exception. Additionally, you gain proficiency in one game set and use of a disguise kit.
- Languages: Through various travels and having to blend into new environments, you gain one additional language of your choosing.
You have, in your journeys, discovered the location of an unclaimed cache of goods. What, exactly, is in this cache is unknown other than the fact that it is valuable. Before entering campaign, either you or the DM should roll on the Highwayman's Cache table to determine what kind of cache it is to determine the variety of loot it will hold. Regardless of the roll, the cache should be equivalent in value to a CR 10 Horde, and have an associated quest attached to finding it and procuring its contents. This quest could be as simple as an encounter to fight monsters or raiders that have stumbled upon the cache, or as complex as piecing together additional information to get in, such as puzzles or more details to fill out your map.
| d8 | Highwayman's Cache |
|---|---|
| 1 | Lost Merchant Caravan |
| 2 | Abandoned Artisan's Workshop |
| 3 | Abandoned Military Outpost |
| 4 | Abandoned Temple |
| 5 | Abandoned Wizard's Tower |
| 6 | Alchemist's Potion Stockpile |
| 7 | Illegal Goods/Contraband Cache |
| 8 | Arms Dealer's Stockpile |
Through your long career of scavenging the arms and regalia of abandoned military camps, robbing from the wealthy, and having the self respect to carefully select your marks, you have gained a certain amount of class and a lot of knowledge of how to use it. When haggling for Inns, Mounts, or any mundane goods or equipment, including in selling them, you gain Advantage on CHA (Persuasion) and (Deception) rolls made for the haggling attempt. You will play yourself as whatever member of society is most like to get the best deal, and the least questions about yourself or your goods.
Additionally, as one who employs these cons, you have advantage on WIS (Insight) rolls made to tell if you're being cheated or overcharged for any reason.
Suggested Characteristics
| d10 | Personality Trait |
|---|---|
| 1 | My first loyalty is to money, whoever pays me has my loyalty. |
| 2 | I never pass up a friendly wager, especially one I think I'll win. |
| 3 | I hold myself and those I'm with to a high standard. I won't tolerate useless people. |
| 4 | Sailors wish they could cuss as well as me, and I'm more than happy to $#@%ing prove it. |
| 5 | A good story is better than an honest one, and I tell good stories. |
| 6 | I could pass for someone of much higher class, and I use it to my advantage whenever I can. |
| 7 | There's always an angle to get ahead, and I'm the one to find it. |
| 8 | I am assured in my wits and my skills. I can talk my way out of most things, and where words fail actions do the talking. |
| 9 | A hard day's work is for farmhands. Call me when there's a fight that needs winning. |
| 10 | Traitors get no quarter, least of all from me. As the old saying goes, snitches get stitches. |
| d6 | Ideal |
|---|---|
| 1 | Fairness. Everyone shares in the work, and everyone shares in the loot. (Lawful) |
| 2 | Freedom. No King, nor land, nor law shall ever bind me or mine from the life we deserve. (Chaotic) |
| 3 | Charity. Kings and Nobles starve the people and tax the poor. What I take gives them hope, and what I give helps them live. (Good) |
| 4 | Profit. At the end of the day, coming out on top is what matters, and money is how you wind up on top. (Evil) |
| 5 | People. My band, my party, my friends, and my family are what matter. Not who they are, or what I will do to keep them alive. (Neutral) |
| 6 | Aspiration. One day, I will be known and respected. What I have to do to get there is just part of the journey. (Any) |
| d8 | Bond |
|---|---|
| 1 | If you fight beside me, I will defend you with my last breath. |
| 2 | My band and I have been together a long time, longer than most of my family kept me around, and I don't intend on changing that. |
| 3 | I was paid well to raid convoys from rival nations, not that my benefactor would ever admit to it. |
| 4 | My childhood love was arranged to marry a noble. I aim to exceed his status and reclaim them however is necessary. |
| 5 | I was sold out by the leader of my last band. Next time we meet, it won't be the authorities to take them. |
| 6 | I have a black book of everyone that's ever wronged me, and once I'm well backed, I'll start crossing out names. |
| 7 | My faithful mount has been with me since I started this journey, and will be with me until I end it. |
| 8 | I keep careful note of everyone that has helped me, either evade the law or just survive in my journeys. I do my best to make sure they're well taken care of in turn. |
| d8 | Flaw |
|---|---|
| 1 | Gambling is a cruel addiction, and I revel in the rush of it. |
| 2 | The work I do has lead me to hard drink. Some nights I can't sleep for the memories of things I've done. |
| 3 | People never took me se-se-seriously because of my st-st-stutter. I t-t-took up this work to sh-show them. |
| 4 | When I took my first life, it was exhilarating. I always hope things go south so I have an excuse to do it again. |
| 5 | I dream big, often bigger than my coin purse allows. |
| 6 | What I can't buy, I'll steal. What I can't steal, I might just be willing to kill for. |
| 7 | I get unsettled staying in one place for too long. Even if I'm not on a wanted board, I always assume I will be sooner or later, and would prefer to be long gone by the time that happens. |
| 8 | If there's a fight I might lose, I will make sure that I make it out alive, regardless of whose foot I need to shoot to make that happen. |
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