William Plunkett — Gentleman Rider and Highwayman

William Plunkett is a mounted robber whose manners are good enough to make victims doubt the encounter until the weapon appears. He prefers controlled theft to bloodshed and cultivates the reputation of a gentleman even while living outside the law.
At a Glance
- Name: William Plunkett
- Species: Human
- Base: Roads between England, Wales and the Irish Sea ports
- Role: Mounted highwayman and duellist
- Alignment: Chaotic Neutral
- Campaign status: Alive and active
- Campaign use: Highwayman, road contact, criminal ally or mounted rival
Game Statistics
5.5e / 2024
William Plunkett — CR 6 humanoid; AC 17; HP 76; Dex 18, Wis 14, Cha 17. Skills Animal Handling +7, Deception +7, Perception +6, Persuasion +7.
Mounted Robbery. While mounted, after Plunkett makes a ranged attack he can move his mount up to half its Speed without provoking Opportunity Attacks from the target.
Courteous Threat. Advantage on Persuasion or Intimidation checks made during a hold-up before violence begins.
Multiattack. Two rapier or light crossbow attacks.
William Plunkett — 5e / 2014
Medium humanoid (human), chaotic neutral
Armor Class 17; Hit Points 76; Speed 30 ft.; Challenge 3 (700 XP; proficiency bonus +2).
STR 12 (+1), DEX 18 (+4), CON 14 (+2), INT 13 (+1), WIS 14 (+2), CHA 17 (+3).
Saving Throws Dex +6, Wis +4; Skills Animal Handling +6 (expertise), Deception +5, Perception +4, Persuasion +5; Senses passive Perception 14; Languages English, French.
Traits
Mounted Robbery. When Plunkett makes a ranged attack from horseback, he may direct his willing mount to move up to half its speed without provoking opportunity attacks from the target of the attack; the move uses his bonus action.
Courteous Threat. Plunkett has advantage on Charisma (Persuasion) or Charisma (Intimidation) checks during a hold-up before violence begins. This doesn’t make a target obey him automatically.
Actions
Multiattack. Plunkett makes two rapier attacks or one light crossbow attack. Loading limits crossbow attacks.
Rapier. Melee Weapon Attack: +6 to hit, reach 5 ft., one target. Hit: 8 (1d8 + 4) piercing damage.
Light Crossbow. Ranged Weapon Attack: +6 to hit, range 80/320 ft., one target. Hit: 8 (1d8 + 4) piercing damage.
Hold the Road (Recharge 5–6). A creature within 30 feet that can hear Plunkett must succeed on a DC 14 Wisdom saving throw or have its speed halved and be unable to take reactions until the end of its next turn, provided Plunkett presents an immediate credible threat.
Bonus Action
Withdraw to Cover. While near his mount, Plunkett can Disengage as a bonus action.
Original 5e/2014 mounted highwayman conversion. His historical partnership belongs to the eighteenth century; the earlier 2024, Pathfinder and 3.5e stats are preserved.
Pathfinder 1e
William Plunkett CR 7; human fighter 2/rogue 4/aristocrat 2. AC 21; hp 66; sneak attack +2d6. Ride +15, Bluff +13, Diplomacy +13, Perception +12. Feats Mounted Combat, Ride-By Attack, Quick Draw, Weapon Finesse.
D&D 3.5e
William Plunkett CR 7; human fighter 2/rogue 4/aristocrat 2. AC 20; hp 56; sneak attack +2d6. Mounted Combat, Ride-By Attack, Quick Draw, Weapon Finesse.
What Is William Plunkett Doing Right Now?
Plunkett is moving stolen correspondence across the Irish Sea because the letters are too dangerous to keep in England. He has not read all of them, which may be the only reason he is still alive.
Meeting William Plunkett
Plunkett greets travellers courteously, names the property he intends to take and offers them a chance to surrender it without bloodshed. If refused, the courtesy disappears quickly.
Encounters
- Plunkett politely asks the party to surrender one sealed packet and ignores all other valuables.
- A port officer knows Plunkett’s horse but not the name he is using this week.
- Plunkett offers the party half the value of stolen goods if they help him avoid a bloodier road gang.
Influence and Tactics
Plunkett fights from horseback whenever possible, keeping distance and controlling the road. He values reputation, avoids needless killing and will honour a clearly stated bargain if doing so does not guarantee his capture.
Appearance and Manner
He dresses like a minor gentleman on the road: good cloak, polished boots, fine horse and weapons kept clean enough to support the illusion of respectability.
Personality
Daring, controlled and vain about his reputation. Plunkett wants victims to remember him as bold rather than brutal.
Relationships
MacLaine: friendly rival and occasional partner. Port contacts: move goods and messages. Officials: frustrated by witnesses who describe him too admiringly.
Equipment and Resources
- Rapier and dagger
- Light crossbow
- Excellent riding horse
- Fine mask and reversible cloak
- Packet of dangerous stolen letters
Running William Plunkett at the Table
Use this NPC as a source of pressure, choice and consequences rather than as a static historical cameo. Their social position, allies, enemies and current problem should matter as much as their combat statistics.
Adventure Hooks
- The Irish Packet: Plunkett needs escort for letters more dangerous than stolen coin.
- The Polite Robbery: The party is robbed without injury, then realises one specific document was the true target.
- MacLaine’s Rival: A friendly competition between two highwaymen starts disrupting military traffic.
- Witness for the Defence: A victim refuses to identify Plunkett because he spared the household.
Connected Places and People
Mythical and Historical Context
The documented William Plunkett was associated with James MacLaine’s highway robberies around 1750, not 1454. This mounted robber is a fictional predecessor adapted for medieval roads, caravans and household retainers. A surviving contemporary account preserved by the Wellcome Collection records Plunkett’s association with MacLaine. Their 1454 partnership here is a deliberate alternative-history invention; James MacLaine’s NPC entry gives a linked encounter.
Historical Inspiration
William Plunkett is adapted from the later gentleman highwayman. His mounted road-crime identity is translated fully into fifteenth-century Britain.
Rules Notes
The game statistics and campaign relationships on this page are original adaptations for the stated rules editions.
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