I've was throwing around some ideas earlier and started playing with an idea for a rogue. This isn't intended for a specific campaign, mainly it's an experiment to see what I could do with the class and perhaps keep as an option the next time I'm looking for a game to join. But I got to thinking it might be worthwhile to share the concept and get some thoughts on it anyway.
So I started playing around with the idea that, if pirates can be rogues, why not highwaymen? If you're not familiar with the concept, a highwayman is a type of criminal that was common in the 18th and 19th century that intercepted and robbed carriages, usually riding on horseback to make a quick get away. Basically, they're like pirates except they travel by road instead of water and rob carriages instead of ships. For some reason they've also been romanticized a lot, much like pirates.
But I started playing around with the idea of a highwayman character and thinking about how it might work in DND. My first thought was that rogue seemed the appropriate class. I was wondering about swashbuckler, though maybe thief would fit better since highwaymen aren't usually known for their dueling prowess.
I've already come up with an idea for a highwayman character and their backstory. Here is what I have come up with. I thought it might be interesting to play around with the romanticization of highwaymen, having this character start off being more like the reality of the job and being forced into the romanticized version out of circumstance.
Estelle Windstriker
Race: Half-Elf
Alignment: Lawful Neutral
Class: Rogue (Swashbuckler)
Background:
The legend of the notorious outlaw Estelle Windstriker began with rough and troubled beginnings. She was the unwanted result of a secret affair between elven and human nobility. Neither wanted her, fearing the affair being exposed. It was finally covered up when the mother pretended the child was her husbands, and then staged a miscarriage while secretly having the infant brought to a local orphanage. Estelle never knew her parents beyond this basic information, though she never felt any inclination to seek them out.
Growing up in the life of a peasant was a tough one. Unfair taxes and the tendency of rich nobles to simply take and take without giving anything back made an honest life frustrating and hopeless. Every time she accomplished something it was taken by some rich bastard. Every time she started to get some money together a sudden arbitrary tax forced her to give it up. An honest life seemed impossible. Being a half-elf didn’t make things any easier. Neither side looked favorably on her.
That changed when she met with a small-time con artist, Randal Buckman, who took her under his wing. He became her best friend when he convinced her that an honest life would never get anywhere. He showed her how to be discreet in this world, how to pick pockets, how to take valuables without drawing attention, how to sneak into places or pocket money without being noticed. And of course how to spot a potentially good score.
They became inseparable and often worked together. Their cons brought in more money, which meant better resources. With better weapons they escalated from pickpocketing to armed robbery, taking anything of value. They acted indiscriminately, striking at anyone who looked like they might have something interesting and escaping pretty quickly. Estelle began to get a thrill out of it, enjoying the luxuries her ill-gotten gains allowed.
And then Estelle had a great idea. They began to notice that many people, especially the wealthy, liked to travel along roads. It was easy to spot rich travellers by the designs of their carriages, too. With the mounting profits of their jobs they quickly acquired horses and began the next big career path. They became highwaymen, pirates of the road. Around the neighbouring area reports began to circulate of a duo of masked robbers who intercepted carriages, violently coercing their occupants into handing over everything of value. Anything was fair game- gold, watches, jewels fancy clothes. Some people were left naked in their carriages after the outlaws were through.
The duo became notorious for their crimes, a reputation which helped tremendously as it made them more intimidating to their victims. But with a great reputation comes unwanted attention. The effects of the robberies were starting to be felt by everyone, and there was no shortage of people who wanted to see Estelle Windstriker and Randal Buckman hanged, drawn and quartered, beheaded, or whatever punishment was decided by the one who actually caught them.
And then it happened, one robbery turned out to be a trap designed to catch them in the act. Randal managed to escape while Estelle was thrown into jail with plans to face the gallows for her crimes. As she faced her inevitable demise, she remained loyal to the end, refusing to give up anything. She would not tell the guards about her accomplice. She was never going to give up the man to whom she owed so much. He had freed her, and she would die free.
Meanwhile, Randall was arrested after being caught in the act of petty theft before he was identified. When his true identity came out and he was faced with the gallows, he began trying to plea for his life. He finally made a deal to give up everything on Estelle in exchange for his release. He told them everything about her, and was released with a full pardon. Estelle was so happy when she saw him, only to see him identify her in front of the guards.
It was a huge slap in the face. The man she trusted with her life had just turned on her to save his own, when she was ready to die for him. It gave her a newfound goal- payback. Whatever it took, wherever he went, Estelle vowed that one way or another she would find him and he would pay for his betrayal. She became determined, managing to use the skills he taught her to pickpocket a guard’s keys and make her escape.
After fleeing from jail, Estelle was faced with one goal—to find and punish Randal. But she had no idea where he went, or where he was now—nor anyone to turn to. She needed to win favor if she was ever going to get anywhere. Which led her to realize she had one skill that could be used for that exact purpose. Nobody in the rich was going to help her, but maybe she could get some from the poor on her side with a little ingenuity.
So Estelle Windstriker returned to the life of a highwayman, robbing rich carriages of all their valuables. But this time she began doing something different. Instead of pocketing the wealth for herself, she began sharing it with others. Though it was difficult at first, she started to make a pretty good career out of robbing the rich and giving to the poor. Her experience getting caught helped her spot any attempts by the authorities, and sure enough the more downtrodden residents started to come around. Though they did not know the specific whereabouts of Randal, a generous sum from one of her jobs was usually more than enough to buy useful information. Deep down, there was a part of her that secretly started to enjoy helping others, though she tried to keep Randal as her primary goal.
Estelle continues her life as a highwayman and has started to develop a decent network among various villages of townsfolk willing to offer favors for decent amounts of coin. Her time in this career has started to give her some rules. She makes a point of only targeting the visibly wealthy, trying not to steal from the poor and downtrodden. She is willing to intimidate but only uses violence in self-defence.
I've also started on a character sheet for her. I tried modifying the standard rogue loadout, replacing the usual shortbow with a set of dual pistols. I gave her high charisma and some bonuses to intimidation which seemed appropriate. This is what I currently have if you're interested:
I was curious to get some other people's thoughts on this idea. I was kinda intrigued by the concept but DND hasn't really established mechanics for a highwayman yet, though in theory it would probably have some similarities to building a pirate.
That might depend on the preferences of the DM, whether they are open to guns in their setting and how they'd be handled. Like one thing I'm wondering, if I have dual pistols, and I draw them both at once, can I fire both of them as a single action or would I need to fire each one on a separate turn
So history supports the idea that highway men and thieves would use hand crossbows over guns. The idea is this, crossbow makes a very quite thunk sound, where as the gun is loud and makes a blast of light. So when more secured carriages came that had people riding before and after it came by, you would not alert them if the need arose to kill someone.
I'm not sure if there are any historical records of thieves actually using wrist crossbows in the 18th century (did those ever actually exist? I'm not sure), but to be fair Dungeons and Dragons isn't usually based on history so much as fantasy settings that might use historical eras and locations as an inspiration for worldbuilding. I could definitely see where a wrist crossbow would be useful if it were available.
Highwaymen also weren't loners. They would often work in small bands, and if they did do their thieving alone they still relied on a support network. Someone had to maintain their horse, and they were always reliant on information. In practical terms, the highwayman is just the face of a larger operation.
I think the best way to go about it isn't with a class, but a custom background that includes a version of the Knight's Retainers feature.
I was actually thinking of the criminal background, which might be a bit more fitting:
You are an experienced criminal with a history of breaking the law. You have spent a lot of time among other criminals and still have contacts within the criminal underworld. You’re far closer than most people to the world of murder, theft, and violence that pervades the underbelly of civilization, and you have survived up to this point by flouting the rules and regulations of society.
This seemed appropriate with the idea of the character having a network.
I'm also wondering if "Gunslinger" fighter would be a more appropriate class.
I feel like their are a few ways to play a highwayman character...
For Rogue, I feel the Swashbuckler Rogue checks off most of the things a highwaymen would do, besieging people on the roadways...they move fast, are good with a sword, can take out most threats one-on-one swiftly...and they're charming enough to convince a noble to surrender, and give up their valuables...and inspiring enough to rally a small group of brigands.
For a horseback highwayman, perhaps a Cavalier Fighter provides an unique opportunity for a Strength-based highwayman...they have abilities that let them charge, hit hard, disorient...good qualities when you're targeting caravans.
As mentioned, if we're doing a powder-based, "Darkest Dungeon" styled highwayman, then a Gunslinger Fighter has merit...likewise, an Artilerist Artificer would have proficiency in firearms, though the flavor of the class is a bit divergent from the image of a highwayman....besides an interest in magical objects.
Scout Rogue is an option for a range-based highwayman...combining their ability to live in the dense areas surrounding the roadways, alongside their ability to make a hasty getaway, lends itself well to a highwayman, and brings a "Ranger" feel to the idea, minus the magic.
I was actually playing around with some of the class options yesterday and started wondering if multiclassing would be a good way to go for a Highwayman. Here's what I came up with:
I was thinking Gunslinger would be the best fit if we're going with the more old-fashioned style of highwayman, which are often shown brandishing dual pistols. Plus it would be a good skill to have if something goes wrong and you have to defend yourself. But as a rogue they'd be better at stealth, which would be good for observing and ambushing potential targets as well as making your getaway. Not to mention it would be handy for navigating towns where you'd want to avoid being recognized. I was thinking Thief would fit this part. So a dual-class gunslinger/thief
But now that you bring it up I could see how scout might work a little better. I hadn't even thought of that one. Reading up on it I think that might be a better choice than thief.
Interesting... R.A. Salvatore. had a fantasy book series called The Crimson Shadow where one of the main characters was the Highway-Halfling. The character actions fit more into the Swashbuckler class.
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I've was throwing around some ideas earlier and started playing with an idea for a rogue. This isn't intended for a specific campaign, mainly it's an experiment to see what I could do with the class and perhaps keep as an option the next time I'm looking for a game to join. But I got to thinking it might be worthwhile to share the concept and get some thoughts on it anyway.
So I started playing around with the idea that, if pirates can be rogues, why not highwaymen? If you're not familiar with the concept, a highwayman is a type of criminal that was common in the 18th and 19th century that intercepted and robbed carriages, usually riding on horseback to make a quick get away. Basically, they're like pirates except they travel by road instead of water and rob carriages instead of ships. For some reason they've also been romanticized a lot, much like pirates.
But I started playing around with the idea of a highwayman character and thinking about how it might work in DND. My first thought was that rogue seemed the appropriate class. I was wondering about swashbuckler, though maybe thief would fit better since highwaymen aren't usually known for their dueling prowess.
I've already come up with an idea for a highwayman character and their backstory. Here is what I have come up with. I thought it might be interesting to play around with the romanticization of highwaymen, having this character start off being more like the reality of the job and being forced into the romanticized version out of circumstance.
Estelle Windstriker
Race: Half-Elf
Alignment: Lawful Neutral
Class: Rogue (Swashbuckler)
Background:
The legend of the notorious outlaw Estelle Windstriker began with rough and troubled beginnings. She was the unwanted result of a secret affair between elven and human nobility. Neither wanted her, fearing the affair being exposed. It was finally covered up when the mother pretended the child was her husbands, and then staged a miscarriage while secretly having the infant brought to a local orphanage. Estelle never knew her parents beyond this basic information, though she never felt any inclination to seek them out.
Growing up in the life of a peasant was a tough one. Unfair taxes and the tendency of rich nobles to simply take and take without giving anything back made an honest life frustrating and hopeless. Every time she accomplished something it was taken by some rich bastard. Every time she started to get some money together a sudden arbitrary tax forced her to give it up. An honest life seemed impossible. Being a half-elf didn’t make things any easier. Neither side looked favorably on her.
That changed when she met with a small-time con artist, Randal Buckman, who took her under his wing. He became her best friend when he convinced her that an honest life would never get anywhere. He showed her how to be discreet in this world, how to pick pockets, how to take valuables without drawing attention, how to sneak into places or pocket money without being noticed. And of course how to spot a potentially good score.
They became inseparable and often worked together. Their cons brought in more money, which meant better resources. With better weapons they escalated from pickpocketing to armed robbery, taking anything of value. They acted indiscriminately, striking at anyone who looked like they might have something interesting and escaping pretty quickly. Estelle began to get a thrill out of it, enjoying the luxuries her ill-gotten gains allowed.
And then Estelle had a great idea. They began to notice that many people, especially the wealthy, liked to travel along roads. It was easy to spot rich travellers by the designs of their carriages, too. With the mounting profits of their jobs they quickly acquired horses and began the next big career path. They became highwaymen, pirates of the road. Around the neighbouring area reports began to circulate of a duo of masked robbers who intercepted carriages, violently coercing their occupants into handing over everything of value. Anything was fair game- gold, watches, jewels fancy clothes. Some people were left naked in their carriages after the outlaws were through.
The duo became notorious for their crimes, a reputation which helped tremendously as it made them more intimidating to their victims. But with a great reputation comes unwanted attention. The effects of the robberies were starting to be felt by everyone, and there was no shortage of people who wanted to see Estelle Windstriker and Randal Buckman hanged, drawn and quartered, beheaded, or whatever punishment was decided by the one who actually caught them.
And then it happened, one robbery turned out to be a trap designed to catch them in the act. Randal managed to escape while Estelle was thrown into jail with plans to face the gallows for her crimes. As she faced her inevitable demise, she remained loyal to the end, refusing to give up anything. She would not tell the guards about her accomplice. She was never going to give up the man to whom she owed so much. He had freed her, and she would die free.
Meanwhile, Randall was arrested after being caught in the act of petty theft before he was identified. When his true identity came out and he was faced with the gallows, he began trying to plea for his life. He finally made a deal to give up everything on Estelle in exchange for his release. He told them everything about her, and was released with a full pardon. Estelle was so happy when she saw him, only to see him identify her in front of the guards.
It was a huge slap in the face. The man she trusted with her life had just turned on her to save his own, when she was ready to die for him. It gave her a newfound goal- payback. Whatever it took, wherever he went, Estelle vowed that one way or another she would find him and he would pay for his betrayal. She became determined, managing to use the skills he taught her to pickpocket a guard’s keys and make her escape.
After fleeing from jail, Estelle was faced with one goal—to find and punish Randal. But she had no idea where he went, or where he was now—nor anyone to turn to. She needed to win favor if she was ever going to get anywhere. Which led her to realize she had one skill that could be used for that exact purpose. Nobody in the rich was going to help her, but maybe she could get some from the poor on her side with a little ingenuity.
So Estelle Windstriker returned to the life of a highwayman, robbing rich carriages of all their valuables. But this time she began doing something different. Instead of pocketing the wealth for herself, she began sharing it with others. Though it was difficult at first, she started to make a pretty good career out of robbing the rich and giving to the poor. Her experience getting caught helped her spot any attempts by the authorities, and sure enough the more downtrodden residents started to come around. Though they did not know the specific whereabouts of Randal, a generous sum from one of her jobs was usually more than enough to buy useful information. Deep down, there was a part of her that secretly started to enjoy helping others, though she tried to keep Randal as her primary goal.
Estelle continues her life as a highwayman and has started to develop a decent network among various villages of townsfolk willing to offer favors for decent amounts of coin. Her time in this career has started to give her some rules. She makes a point of only targeting the visibly wealthy, trying not to steal from the poor and downtrodden. She is willing to intimidate but only uses violence in self-defence.
I've also started on a character sheet for her. I tried modifying the standard rogue loadout, replacing the usual shortbow with a set of dual pistols. I gave her high charisma and some bonuses to intimidation which seemed appropriate. This is what I currently have if you're interested:
https://www.dndbeyond.com/profile/Chickadee42/characters/56614706
I was curious to get some other people's thoughts on this idea. I was kinda intrigued by the concept but DND hasn't really established mechanics for a highwayman yet, though in theory it would probably have some similarities to building a pirate.
You can always treat a hand crossbow as a pistol in game terms.
Using Points Buy you can start as a Half-Elf with stats 10/14/12/14/14/14 which would improve your stats a little.
That might depend on the preferences of the DM, whether they are open to guns in their setting and how they'd be handled. Like one thing I'm wondering, if I have dual pistols, and I draw them both at once, can I fire both of them as a single action or would I need to fire each one on a separate turn
I don't think there's any rules for dual wielding pistols, but I think your DM and you could come up with something.
So history supports the idea that highway men and thieves would use hand crossbows over guns. The idea is this, crossbow makes a very quite thunk sound, where as the gun is loud and makes a blast of light. So when more secured carriages came that had people riding before and after it came by, you would not alert them if the need arose to kill someone.
I'm not sure if there are any historical records of thieves actually using wrist crossbows in the 18th century (did those ever actually exist? I'm not sure), but to be fair Dungeons and Dragons isn't usually based on history so much as fantasy settings that might use historical eras and locations as an inspiration for worldbuilding. I could definitely see where a wrist crossbow would be useful if it were available.
Highwaymen also weren't loners. They would often work in small bands, and if they did do their thieving alone they still relied on a support network. Someone had to maintain their horse, and they were always reliant on information. In practical terms, the highwayman is just the face of a larger operation.
I think the best way to go about it isn't with a class, but a custom background that includes a version of the Knight's Retainers feature.
I was actually thinking of the criminal background, which might be a bit more fitting:
You are an experienced criminal with a history of breaking the law. You have spent a lot of time among other criminals and still have contacts within the criminal underworld. You’re far closer than most people to the world of murder, theft, and violence that pervades the underbelly of civilization, and you have survived up to this point by flouting the rules and regulations of society.
This seemed appropriate with the idea of the character having a network.
I'm also wondering if "Gunslinger" fighter would be a more appropriate class.
I feel like their are a few ways to play a highwayman character...
For Rogue, I feel the Swashbuckler Rogue checks off most of the things a highwaymen would do, besieging people on the roadways...they move fast, are good with a sword, can take out most threats one-on-one swiftly...and they're charming enough to convince a noble to surrender, and give up their valuables...and inspiring enough to rally a small group of brigands.
For a horseback highwayman, perhaps a Cavalier Fighter provides an unique opportunity for a Strength-based highwayman...they have abilities that let them charge, hit hard, disorient...good qualities when you're targeting caravans.
As mentioned, if we're doing a powder-based, "Darkest Dungeon" styled highwayman, then a Gunslinger Fighter has merit...likewise, an Artilerist Artificer would have proficiency in firearms, though the flavor of the class is a bit divergent from the image of a highwayman....besides an interest in magical objects.
Scout Rogue is an option for a range-based highwayman...combining their ability to live in the dense areas surrounding the roadways, alongside their ability to make a hasty getaway, lends itself well to a highwayman, and brings a "Ranger" feel to the idea, minus the magic.
I was actually playing around with some of the class options yesterday and started wondering if multiclassing would be a good way to go for a Highwayman. Here's what I came up with:
https://ddb.ac/characters/56614706/1jJCus
I was thinking Gunslinger would be the best fit if we're going with the more old-fashioned style of highwayman, which are often shown brandishing dual pistols. Plus it would be a good skill to have if something goes wrong and you have to defend yourself. But as a rogue they'd be better at stealth, which would be good for observing and ambushing potential targets as well as making your getaway. Not to mention it would be handy for navigating towns where you'd want to avoid being recognized. I was thinking Thief would fit this part. So a dual-class gunslinger/thief
But now that you bring it up I could see how scout might work a little better. I hadn't even thought of that one. Reading up on it I think that might be a better choice than thief.
Interesting... R.A. Salvatore. had a fantasy book series called The Crimson Shadow where one of the main characters was the Highway-Halfling. The character actions fit more into the Swashbuckler class.