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It frames the highwayman as a stylish gun-and-blade rogue who strikes at the ruling classes, with encounters that invert ordinary justice for a moment. The document then details a progression of combat features by level, including pistol-and-rapier tactics, stealth ambush benefits, lunging rapier attacks, weapon finesse advantages, and a dramatic swordsman display that can impose disadvantage. It also specifies a flintlock pistol’s stats, costs, and loading requirements, and includes credits and legal licensing references to SRD 5.1 materials.",{"@graph":69,"@context":122},[70,84,105],{"@type":71,"itemListElement":72},"BreadcrumbList",[73,77,79,82],{"item":74,"name":75,"@type":76,"position":8},"https://docshare.wps.com","Home","ListItem",{"item":78,"name":9,"@type":76,"position":14},"https://docshare.wps.com/document/",{"item":80,"name":10,"@type":76,"position":81},"https://docshare.wps.com/document/story-novel/",3,{"item":83,"name":65,"@type":76,"position":19},"https://docshare.wps.com/document/highwayman-carve-an-adventurers-path-with-pistol-and-rapier/510886/",{"url":83,"name":65,"@type":85,"image":86,"author":91,"headline":65,"publisher":94,"fileFormat":97,"inLanguage":63,"description":67,"dateModified":98,"datePublished":99,"encodingFormat":97,"isAccessibleForFree":100,"interactionStatistic":101},"DigitalDocument",{"url":87,"@type":88,"width":89,"height":90},"https://docshare.wps.com/thumbnails/highwayman-carve-an-adventurers-path-with-pistol-and-rapier/510886.png","ImageObject",300,407,{"name":92,"@type":93},"Damian","Person",{"url":74,"name":95,"@type":96},"DocShare","Organization","application/pdf","2026-10-28","2026-10-06",true,{"@type":102,"interactionType":103,"userInteractionCount":19},"InteractionCounter",{"@type":104},"ViewAction",{"@type":106,"mainEntity":107},"FAQPage",[108,114,118],{"name":109,"@type":110,"acceptedAnswer":111},"What kind of character is the highwayman described as?","Question",{"text":112,"@type":113},"The highwayman is a gun-and-blade slinger who uses pistol and rapier with style, bravery, and calculated ambush tactics.","Answer",{"name":115,"@type":110,"acceptedAnswer":116},"What does the document say about pistol and rapier mechanics at level 3?",{"text":117,"@type":113},"It describes keeping up to three pistols for rapid firing, firing a pistol on the Attack action with a +2 to hit, and making a rapier attack in melee while firing a loaded pistol as a bonus action.",{"name":119,"@type":110,"acceptedAnswer":120},"What are the key combat and utility features at higher levels (9, 13, and 17)?",{"text":121,"@type":113},"Level 9 adds a lunging rapier attack with extra piercing damage on a successful strike; level 13 grants bonuses with light/finesse weapons and allows bonus-action firing and reloading when wielding one pistol; level 17 enables a skill display that can force disadvantage after a failed Wisdom saving throw.","https://schema.org",{"og:url":83,"og:type":124,"og:title":65,"og:site_name":95,"og:description":67},"article",{"robots":126,"canonical":83},"index,follow",{"doc_id":128,"site_id":62},510886,1792178390,{"code":4,"msg":5,"data":131},{"doc_id":128,"user_id":132,"nickname":92,"user_avatar":133,"doc_module":4,"category_id":8,"category_name":10,"doc_title":65,"doc_description":67,"doc_content":134,"file_id":135,"file_url":136,"file_type":137,"file_size":138,"view_count":19,"is_deleted":4,"is_public":8,"is_downloadable":8,"audit_status":8,"page_count":81,"language":139,"language_code":63,"site_id":62,"html_lang":63,"table_of_contents":140,"faqs":141,"seo_title":142,"seo_description":67,"update_tm":143,"read_time":24},137451208677,"https://ap-avatar.wpscdn.com/davatar_155a257f0dc6eb9ab79c44ca47cae57d","Highwayman   \nCarve an Adventurer's Path with Pistol and Rapier  \nThere are those of us, or them rather, who have much more than they need. Perhaps they have worked hard for it. More likely than not, they were born to it. Never knowing need. Always having what they want, regardless of price or rarity.  \nIs it fair? That makes little difference, because what it is is life, an endless series of unfair acts and consequences for the majority.  \nJust as the wealthy are able to skirt many of the injustices the rest of us face daily, there are a few unfortunate events that call upon the privileged whether they want them to or not. One of these things is death.  \nAnd while they might avoid the hand of the taxman, they'll surely be found by the highwayman.  \nDespite the care taken, the guards hired, the decoy carriages, the secrecy in planning, the rich can be labeled victim when in the sights of these robbers, these dangerous villains as they are called.  \nThe highwayman, with pistol and rapier, nerves of steel, and privates of brass, has the bravery and gaul towrest the rich of their bounty. Whether they share their ill-gotten gains with the poor or build their own empire of thieves in the darkest woods, they strike at the heart of the ruling classes, reminding them of their temporary nature, their mortality and frailty.  \nFor that brief moment at swordpoint, the world is turned topsy turvy, and justice is more than a vague concept. For some, the highwayman is a hero, for some an outlaw. For the highwayman, it's the rush of the hunt, bagging the quarry, taking its treasure, and leaving it with all its vulnerabilities exposed. It's comeuppance delivered with bravado and grace.  \nAs a highwayman, you are a gun and blade slinger. A rogue with style and panache. A left-leaning Scarlet Pimpernel, a Zorroesque swashbuckler, Robin Hood with a pistol, you are all these things and more.  \nOf course, life is more than stealing from the wealthy.  \nOftentimes a person needs a healthy diversion, and, for a highwayman, what better than adventure, chasing glittering treasure and facing fierce monsters. Especially during those times when the king's men are getting a little too close for comfort, it's hard to find a better hiding place than in a dungeon.  \nLevel 3: Pistol and Rapier  \nAs a highwayman, you are proficient with firearms if your DM allows them in your campaign.  \nYou may keep up to three pistols in your belt so that you can fire them in combat without having to reload. At range, you may fire a pistol with a +2 bonus to hit if you take the Attack action as your only action. In melee you may make a rapier attack with your main hand and fire one of your loaded pistols as a bonus action.  \nLevel 3: TheArt of Ambush  \nWhen you attack from a position of Stealth, you have advantage on your initiative roll and do an additional die of damage on any weapon attacks you make in your first  \nround of combat Image: Midjourney  \nLevel 9: Lunging Attack  \nA number of times per long rest equal to your Dexterity bonus, as an action, you can make a lunging attack with your rapier with a range of up to 10 feet. On a successful strike, you do an extra damage die plus your Strength modifier (minimum of 1) of piercing damage.  \nLevel 13: Weapon Finesse  \nWhen using a weapon with the light or finesse properties, you gain a +2 bonus on your attack and damage rolls. Additionally, if only using one pistol in your main hand and your other hand is free, you may fire your weapon and reload it as a bonus action.  \nLevel 17: Swordsman's Display  \nThree times per long rest, as a bonus action, you can make a display of skill mastery that gives an enemy pause—writing your initial on their skin with a flick of your rapier, doing a backflip, cutting candles in half without them moving, etc. If they fail a Wisdom saving throw against a DC of 8 + your Dexterity bonus + your proficiency bonus, their next attack, saving throw, or ability check is made with disadvantage.  \nFlintlock Pistol  \n","cbCaiiC6dPg9KYPC","https://ap.wps.com/l/cbCaiiC6dPg9KYPC","pdf",13886775,"English","# Highwayman\n## Level 3: Pistol and Rapier\n## Level 3: TheArt of Ambush\n## Level 9: Lunging Attack\n## Level 13: Weapon Finesse\n## Level 17: Swordsman's Display\n## Flintlock Pistol\n## Credits\n## Legal","[{\"question\":\"What kind of character is the highwayman described as?\",\"answer\":\"The highwayman is a gun-and-blade slinger who uses pistol and rapier with style, bravery, and calculated ambush tactics.\"},{\"question\":\"What does the document say about pistol and rapier mechanics at level 3?\",\"answer\":\"It describes keeping up to three pistols for rapid firing, firing a pistol on the Attack action with a +2 to hit, and making a rapier attack in melee while firing a loaded pistol as a bonus action.\"},{\"question\":\"What are the key combat and utility features at higher levels (9, 13, and 17)?\",\"answer\":\"Level 9 adds a lunging rapier attack with extra piercing damage on a successful strike; level 13 grants bonuses with light/finesse weapons and allows bonus-action firing and reloading when wielding one pistol; level 17 enables a skill display that can force disadvantage after a failed Wisdom saving throw.\"}]","Highwayman - Carve an Adventurer's Path with Pistol and Rapier | PDF",1791245877]