Laurens de Graaf — Buccaneer Captain

At a Glance
| Name | Laurens Cornelis Boudewijn de Graaf; called Laurencillo or Lorencillo in Spanish ports |
|---|---|
| Role | Dutch-born sea captain, buccaneer and prize negotiator |
| Campaign Year | 1454 CE |
| Base | Tortuga, with voyages across the Caribbean Sea and the Gulf approaches |
| Faction | Brethren of the Coast; commands his own crew under agreed ship’s articles |
| Alignment | Chaotic Neutral — resists distant rule, keeps bargains with his crew, takes prizes by force and will not sacrifice hostages casually |
| Allies | Anne Dieu-le-Veut, Michel de Grammont and captains willing to abide by the division of prizes |
| Opponents | Foreign naval patrols, cheated prize claimants, captains who break crew agreements and rival merchants |
| Languages | Dutch, French, Spanish; conversational languages learned at sea |
| Reputation | A gifted navigator and dangerous boarding captain; prefers a hard bargain to a ruinous fight |
The captain has brought his ship into Tortuga with three holds’ worth of stolen cargo and a fourth hold full of prisoners. His sailors want their shares; a rival claims the richest chest; a merchant’s daughter says that chest is hers. Laurens de Graaf places his blade on the table and asks who can prove a claim before his crew decides the question with fists.
De Graaf is the man to see when a ship needs a daring pilot, a prize needs to be sold discreetly or a captain needs to survive a failed raid. He can be generous to those who keep their word and ruthless to a wealthy enemy who refuses a ransom. He is no folk hero. Coastal families fear his sails for good reason, and the fact that he limits some atrocities does not excuse the ships he has taken.
What Is Happening Right Now?
The stolen ledger. A clerk disappeared after recording the distribution of an intercepted merchant cargo. Without his ledger, the sailors cannot agree on their shares; two captains now claim the same chest, while the missing clerk’s brother insists the papers were taken to Port Royal.
The captive’s bargain. One prisoner can identify a secret inlet used by foreign warships. De Graaf will release her for the information, but one of his lieutenants wants her kept until a larger ransom arrives. The captain has not yet learned that the lieutenant plans to sell her without his consent.
The choice: The characters can find the ledger, protect the prisoner, expose the lieutenant or escort the prize to a neutral harbour. De Graaf pays for useful work but insists on knowing exactly whom the party serves.
The Captain Behind the Reputation
Laurens reads wind and men with the same restless attention. He listens while other captains boast, notices who reaches for a knife and remembers a small injustice against his crew for years. His sailors find him disciplined at sea and quarrelsome ashore. He is proud of his reputation, even when it makes a peaceful negotiation harder.
What he values. Competent pilots, fairly declared shares and the freedom of crews to elect their own terms of service. He rewards courage shown in a rescue more readily than cruelty shown to helpless captives.
What he excuses. Violent seizure of cargo, intimidation of merchants and the capture of prisoners for ransom. He may punish an officer for mistreating hostages yet refuse to return the stolen goods. This is the hard edge of his Chaotic Neutral conduct: loyalty and personal restraint exist beside exploitation.
How he deals with the characters. Show him evidence or solve a problem and he will hear you. Threaten his crew, lecture him about freedom while accepting his stolen coin, or break a bargain and he becomes a lasting enemy. He prefers to leave a room with more options than when he entered it.
Allies, Rivals and the Brethren
Brethren of the Coast. De Graaf supports the free harbours and their right to defend themselves, but does not command the whole republic. He must answer to his own ship’s articles and persuade fellow captains to cooperate. His independence can make him useful in a crisis and difficult at a council.
Anne Dieu-le-Veut. An accomplished captain and formidable partner, never his lieutenant by default. They respect each other’s courage, argue over methods and are especially dangerous when rivals mistake disagreement for weakness.
Michel de Grammont. A rival strategist and occasional ally whose plans can demand too much from ordinary sailors. A common enemy can unite them for a voyage; the division of the prize can divide them again.
Henry Morgan. A captain with his own ambitions and following. Laurens will bargain with him, but neither man surrenders the right to command his own deck.
The harbours. Tortuga offers sympathetic crews, shipwrights and argumentative councils; Port Royal is a tempting but politically uncertain place to sell cargo, find a buyer or meet a spy. Farther away, the merchants of New Amsterdam can move goods without asking awkward questions—at a price.
Adventure Hooks
The Captain’s Ledger
Someone has altered the prize shares after a bloody boarding. The forgery will cause a mutiny unless the characters find the clerk before the next tide. The clerk is alive, but a faction within the Brethren wants his evidence destroyed before the council can hear it.
The Wrong Ship
A vessel flying De Graaf’s colours burns a village and takes children as hostages. He insists it was not his ship, yet the raiders know his signals. The characters must discover whether the attack was a false flag, a rogue officer or a captain he has secretly protected.
The Safe Anchorage
A pilot promises a hidden inlet near Campeche, but it is already used by local fishing families and an armed patrol. De Graaf will pay for a passage that does not bring a warship down on the settlement. The party can negotiate safe use, warn the families or uncover the pilot’s treachery.
Where to Find Laurens de Graaf
Seek him aboard his flagship off Tortuga, in a dockside counting room settling a disputed prize, or at a tense council of the Brethren of the Coast. He travels lightly ashore with one or two trusted sailors. His ship is more dangerous than any blade he carries: it has lookouts, a disciplined watch and men who know how to fight together.
Appearance and Equipment
Weathered by sun and spray, Laurens dresses as a prosperous seafarer rather than a pantomime pirate. A practical broad-brimmed hat, sea cloak, fitted jacket, boots and belt suit the early maritime setting. He carries a finely balanced cutlass, dagger, and a compact crossbow when going ashore. Gnome-built early firearms exist in some ports, but a later flintlock pistol and the familiar tricorn hat do not define his equipment in 1454.
Laurens de Graaf — Game Statistics
De Graaf is a skilled mortal captain. His greatest advantage is an experienced crew, not supernatural invulnerability or a lair that magically produces sailors. His ship, guns and trained boarding parties are separate encounter threats.
Laurens de Graaf
Medium Humanoid (Human), Chaotic Neutral
- AC
- 17 (studded leather, Defense fighting style)
- Initiative
- +4 (14)
- HP
- 142 (19d8 + 57)
- Speed
- 30 ft.
| STR | DEX | CON | INT | WIS | CHA |
|---|---|---|---|---|---|
| 12Mod +1 · Save +1 | 18Mod +4 · Save +7 | 16Mod +3 · Save +3 | 14Mod +2 · Save +2 | 14Mod +2 · Save +5 | 16Mod +3 · Save +3 |
- Skills
- Acrobatics +7, Athletics +4, Deception +6, Insight +5, Perception +8, Persuasion +6, Stealth +10
- Senses
- Passive Perception 18
- Languages
- Dutch, French, Spanish
- CR
- 7 (2,900 XP; PB +3)
Traits
Defense. While wearing armour, Laurens gains a +1 bonus to AC (included above).
Sea Legs. Laurens has Advantage on Dexterity saving throws to avoid falling Prone on a pitching deck or moving platform.
Opportunist. Once on each of his turns, Laurens deals an extra 17 (5d6) damage with a Cutlass hit if he has Advantage on the attack roll, or an ally is within 5 feet of the target and Laurens doesn’t have Disadvantage.
Actions
Multiattack. Laurens makes three Cutlass attacks. He can replace one of these attacks with a Light Crossbow attack.
Cutlass. Melee Attack Roll: +7, reach 5 ft. Hit: 8 (1d8 + 4) Slashing damage.
Light Crossbow. Ranged Attack Roll: +7, range 80/320 ft. Hit: 8 (1d8 + 4) Piercing damage; loading applies.
Bonus Actions
Boarding Order (Recharge 5–6). One ally Laurens can see within 30 feet who can hear him can move up to half its Speed without provoking Opportunity Attacks.
Reactions
Parry. Laurens adds 3 to his AC against one melee attack that would hit him, provided he can see the attacker and is wielding his cutlass.
Gear: Cutlass, dagger, light crossbow, spare cord and charts; Laurens carries no enchanted equipment by default.
Laurens de Graaf
Medium humanoid (human), chaotic neutral
- Armor Class
- 17 (studded leather, Defense fighting style)
- Hit Points
- 142 (19d8 + 57)
- Speed
- 30 ft.
| STR | DEX | CON | INT | WIS | CHA |
|---|---|---|---|---|---|
| 12+1 | 18+4 | 16+3 | 14+2 | 14+2 | 16+3 |
- Saving Throws
- Dex +7, Wis +5
- Skills
- Acrobatics +7, Athletics +4, Deception +6, Insight +5, Perception +8, Persuasion +6, Stealth +10
- Senses
- passive Perception 18
- Languages
- Dutch, French, Spanish
- Challenge
- 7 (2,900 XP)
Defense. While wearing armour, Laurens gains a +1 bonus to AC (included above).
Sea Legs. Laurens has advantage on Dexterity saving throws made to avoid falling prone while aboard a moving ship or platform.
Opportunist. Once per turn, Laurens deals an extra 17 (5d6) damage when he hits a target with a cutlass attack and has advantage on the attack roll, or when an ally is within 5 feet of the target and Laurens doesn’t have disadvantage.
Actions
Multiattack. Laurens makes three cutlass attacks. One may be replaced with a light crossbow attack.
Cutlass. Melee Weapon Attack: +7 to hit, reach 5 ft., one target. Hit: 8 (1d8 + 4) slashing damage.
Light Crossbow. Ranged Weapon Attack: +7 to hit, range 80/320 ft., one target. Hit: 8 (1d8 + 4) piercing damage; loading applies.
Bonus Actions
Boarding Order (Recharge 5–6). One ally within 30 feet who can hear Laurens can move up to half its speed without provoking opportunity attacks.
Reactions
Parry. Laurens adds 3 to his AC against one melee attack that would hit him if he can see the attacker and is wielding his cutlass.
Equipment: Cutlass, dagger, light crossbow, maps and seafarer’s kit.
Laurens de Graaf — CR 9
XP 6,400
Human fighter 6/rogue 4
CN Medium humanoid (human)
Init +8; Senses Perception +15
DEFENSE
- AC
- 19, touch 15, flat-footed 19 (uncanny dodge; +4 armour, +4 Dex, +1 dodge)
- hp
- 71 (6d10 + 4d8 + 20)
- Fort
- +8
- Ref
- +10
- Will
- +4
- Defensive Abilities
- evasion, uncanny dodge
OFFENSE
- Speed
- 30 ft.
- Melee
- masterwork rapier +16/+11 (1d6+5/18–20)
- Ranged
- masterwork light crossbow +14 (1d8/19–20)
- Special Attacks
- sneak attack +2d6
STATISTICS
- Str
- 14
- Dex
- 18
- Con
- 14
- Int
- 14
- Wis
- 12
- Cha
- 16
- Base Atk
- +9
- CMB
- +11
- CMD
- 26
Feats: Combat Expertise, Dodge, Improved Feint, Improved Initiative, Mobility, Point-Blank Shot, Precise Shot, Quick Draw, Weapon Finesse, Weapon Focus (rapier), Weapon Specialization (rapier)
Skills: Acrobatics +15, Bluff +15, Diplomacy +15, Knowledge (geography) +12, Perception +13, Profession (sailor) +14, Sense Motive +11, Stealth +15, Swim +9
Languages: Dutch, French, Spanish
Rogue Abilities: Evasion, rogue talents (combat trick, fast stealth), trapfinding +2, trap sense +1, uncanny dodge.
Fighter Abilities: Armor training 1 (reduce armour check penalty by 1), bravery +2 on Will saves against fear, weapon training (light blades +1; included in rapier attack and damage).
TACTICS
Before Combat: De Graaf stations lookouts and keeps a retreat route open.
During Combat: He flanks with trained sailors, uses feints when isolated and avoids prolonged fights against superior numbers.
Morale: He withdraws when his crew or prisoners would be lost for no gain.
Gear: Masterwork rapier, masterwork chain shirt, masterwork light crossbow, chart case, rope and seafaring equipment.
Laurens de Graaf
Medium Humanoid (Human); Chaotic Neutral
- Hit Dice
- 6d10 + 4d6 + 20 (67 hp)
- Initiative
- +8
- Speed
- 30 ft. (6 squares)
- Armor Class
- 18 (+4 Dex, +4 armour), touch 14, flat-footed 18 (uncanny dodge); Dodge +1 against designated opponent
- Base Attack/Grapple
- +9/+11
- Attack
- Masterwork rapier +15 melee (1d6+4/18–20)
- Full Attack
- Masterwork rapier +15/+10 melee (1d6+4/18–20)
- Space/Reach
- 5 ft./5 ft.
SAVES AND ABILITIES
- Fort
- +8
- Ref
- +10
- Will
- +4
- Str
- 14
- Dex
- 18
- Con
- 14
- Int
- 14
- Wis
- 12
- Cha
- 16
SPECIAL ATTACKS AND QUALITIES
Special Attacks: Sneak attack +2d6.
Special Qualities: Evasion, trapfinding, trap sense +1, uncanny dodge.
Swashbuckling Tactics: De Graaf uses Tumble to move into flanking positions, feints when isolated and orders nearby sailors to cover a retreat.
SKILLS AND FEATS
Skills: Balance +8, Bluff +14, Diplomacy +14, Intimidate +12, Knowledge (geography) +7, Listen +6, Profession (sailor) +12, Sense Motive +7, Spot +7, Swim +8, Tumble +13, Use Rope +11.
Feats: Combat Expertise, Dodge, Improved Feint, Improved Initiative, Mobility, Weapon Finesse, Weapon Focus (rapier), Weapon Specialization (rapier), Leadership.
Languages: Dutch, French, Spanish.
ENCOUNTER DETAILS
- Environment
- Warm maritime settlements and coastlines
- Organization
- Solitary or captain with 4–20 sailors
- Challenge Rating
- 10
- Treasure
- NPC equipment and prize shares
- Alignment
- Chaotic Neutral
- Advancement
- By character class
Possessions: Masterwork rapier, masterwork chain shirt, light crossbow, charts and sailor’s kit. Crew members are separate creatures with their own initiatives.
From the Low Countries to the Caribbean
The deeds that made Laurens de Graaf famous belong, in ordinary history, to the later seventeenth century. The Dutch-born captain was active in the Caribbean and appears in accounts of the attack on Veracruz in 1683 and later campaigning near Campeche. His later life was entangled with shifting commissions, rival captains and French colonial affairs. Here he is already an established captain in 1454, when maritime power belongs to different kingdoms and city-states, and those later dates are not used as dates of events in the campaign.
His earlier connection to the Low Countries is Dutch-speaking rather than citizenship in a future Dutch Republic. The real captain’s exploits provide a model for a navigator, raider and sometimes more restrained commander; the named 1454 disputes and shipboard crises are current adventures, not claims that seventeenth-century voyages had occurred.
Historical Portrait and Sources

The Regional Archives of Dordrecht records de Graaf’s birth and career, while World History Encyclopedia describes his Caribbean raids and changing alliances. These are historical sources for the figure behind the character, not a timetable that this campaign must follow.
Connected Ports and People
Brethren of the Coast · Tortuga · Caribbean Sea · Port Royal · Anne Dieu-le-Veut · Michel de Grammont · Caribbean NPCs
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