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Captain Thomas Whetstone

Human · Noble · Level 5

Captain Thomas Whetstone

Pirate Captain
“the gentleman who sent word.”
ACNone
HP12/12
Init
STR
DEX
CON
INT
WIS
CHA
ConditionsNone

At the table

Voice

A dry, salt-roughened voice shaped by shipboard orders, with the measured diction of his upbringing still caught beneath the adopted bluntness. He does not raise his voice to sound dangerous; he makes each word land as if it were part of an account that will eventually be collected.

His voice carries the dry scrape of salt air and a controlled breath learned from giving orders over wind and deck noise. Words are clipped when work is underway, but older, polished phrasing slips through when he is tired, angry, or trying to persuade someone. He pronounces names carefully, as if each one might later be evidence.

Speech patterns

Uses complete, measured sentences even when pretending to be a common captain.
Employs nautical bluntness in public, then lets formal turns of phrase slip when irritated or tired.
Avoids naming Teach directly when strangers are near, referring instead to 'the gentleman who sent word.'
Frames threats as practical outcomes rather than emotional promises.

How to play them

Presents himself as a practical captain seeking hands for dangerous work. He offers clear pay and a narrow version of the truth, watching closely for anyone who recognizes his manners. If challenged about the missing crew, he redirects toward the coming British ships or offers information useful enough to purchase a delay.

Goal

Get Jack Drummond and a replacement crew out of Nassau before the British arrive, without allowing anyone to connect Whetstone to Major Stede Bonnet.

Motivation

To survive the collapse of the life he chose without surrendering the last traces of the life he abandoned.

Secret · GM only

Appearance

A lean, carefully held man whose clothes have been made to pass for a captain's rough working dress, though the fit is too considered and the seams too well tended. His hands are broad at the knuckles, permanently roughened by rope and salt, but he handles a cup as if it were fragile china. He moves with economical steps, placing his feet as though the deck might roll beneath him. The unexpected detail is a small, neatly folded square of fine linen tucked inside one boot, protected from the weather more carefully than his powder.

Clothing

A salt-dark coat, worn shirt, plain waistcoat, and scuffed boots chosen to look ordinary. The coat is serviceable but conspicuously well fitted, with one cuff repeatedly mended in fine thread. He has removed the ornaments that would mark his station, though he still keeps his linen clean when circumstances allow.

Body language

Keeps his shoulders level and his chin composed even in a press of armed men. His hands betray him: one thumb smooths an imaginary crease along his cuff whenever he has been recognized, while his fingers curl toward the cutlass when he is weighing a lie.

Height
About 5 feet 10 inches
Build
Lean, upright, and stronger than his careful posture suggests
Eyes
Dark brown
Hair
Dark brown, powdered-looking with salt when unwashed
Skin
Weathered, pale skin browned and roughened by salt and sun
Age
Adult, in his late thirties
Gender
Male
Size
Average human

Distinguishing features

His hands are rope-rough, but he folds and handles small objects with conspicuous care.
His clothes are dressed down, yet the tailoring remains too precise for a man claiming not to care how he looks.
A fine linen square is hidden inside one boot, kept clean despite the grime of the port.

Personality

13 traits and drives

Whetstone is disciplined enough to make panic look like patience, yet the discipline is brittle when his identity is threatened. He can show genuine consideration toward a frightened stranger, then calmly use that stranger as cover. In company he performs roughness; alone he repairs small things with the meticulous care of a man trying to prove his former life was not entirely lost.

Alignment
Self-preserving, with a capacity for calculated loyalty

Quirks

Smooths an imaginary crease along his cuff when someone says his real name or watches him too closely.
Counts a room’s doors under his breath, but never counts windows.
Turns his cup so its handle points toward the nearest exit.
Refolds scraps of paper into exact squares while listening to bad news.

Habits

Checks exits and sightlines before settling anywhere, then pretends the choice was casual.
Gives orders as requests when watched and as commands when the door is shut.
Pays promptly when he wants silence, but remembers every debt he cannot afford to settle.
When forced to choose between a crewman and an escape route, calculates for a moment too long.

Traits · 3

Courteous by instinct, suspicious by necessity.
Can be genuinely attentive to another person’s distress, but rarely lets compassion change his plan.
Prefers clean arrangements and hates being made to improvise in front of witnesses.

Flaws · 3

His gentlemanly habits survive his disguise and can expose him to anyone who knows what to watch for.
He treats people as pieces in an escape plan when frightened.
He mistakes a controlled appearance for control of the situation.

Fears · 3

Being recognized as Major Stede Bonnet before he can leave Nassau.
Teach deciding that Drummond and Whetstone have become liabilities.
The crew learning that their deaths were not accidents.

Wants and needs · 4

A usable route past the port blockade
A crew that does not know his former identity
Proof that Drummond’s extraction is still worth the risk
A moment alone in which no one expects him to perform Captain Whetstone

Combat

HP 12 · Normal human movement

Avoids a fair fight. He fires once to break an opponent’s nerve or open a route, then uses cover and the cutlass to force a passage toward an exit. If the odds turn against him, he bargains, retreats, or sacrifices someone else’s position to buy time. His armor reduces incoming damage by d2.

Captain Thomas Whetstone

Average human humanoid (human), self-preserving, with a capacity for calculated loyalty
Armor ClassNot set
Hit Points12
SpeedNormal human movement
Level5
STR
DEX
CON
INT
WIS
CHA
SensesOrdinary human senses
Languages
English
Custom creature feature. Gentleman’s Measure. Once per fight, Whetstone can turn a brief exchange of words into a chance to reposition or withdraw, provided his opponent can hear him and is not already attacking.

Actions

Cutlass. Cutlass: inflicts d6 damage. In a close press he uses the sword compactly, aiming for hands, ribs, and the space beneath an arm.
Flintlock shot. Flintlock pistol: inflicts d8 damage, then requires reloading. The shot is loud enough to draw attention from nearby streets and rooms.

Services they sell

Hiring and organizing a small crew
Passage aboard his ship if the escape succeeds
Knowledge of pirate customs and the pressures dividing Nassau’s captains

Rewards they can give

Pay for helping assemble a crew, though he may try to delay payment until they are aboard.
A harbor sketch and useful knowledge of Nassau’s watched routes.
A chance to leave the island with Whetstone, Drummond, and the survivors of the coming violence.

Equipment

  • Padded coat beneath his outer coat (armor)Light armor, reducing incoming damage by d2.
  • Cutlass (weapon)A serviceable blade; inflicts d6 damage.
  • Flintlock pistol (weapon)A flintlock pistol; inflicts d8 damage and must be reloaded after firing.
  • Captain’s stores (supplies)Powder, shot, a folded harbor sketch with marks that may be outdated, and a packet of fine linen.

Possessions

A folded square of fine linen hidden inside one boot
A plain signet kept wrapped in cloth
A short harbor sketch marked with possible escape routes
A packet of correspondence from Edward Teach

Background

Major Stede Bonnet was born to privilege and learned the manners of a gentleman before the sea taught him their limits. He took to piracy with more money than experience, and his association with Edward Teach and Benjamin Hornigold placed him among men who understood violence as work rather than theater. That difference has never left him. A formative season under Teach taught Bonnet that a crew can become a liability the instant it knows too much. A week ago he came to Nassau under the name Captain Thomas Whetstone, changed the look and name of his ship, and ordered his crew to keep out of sight while he handled business ashore. Teach’s secret message asked him to extract Jack Drummond under that alias. Then rumors spread that Hornigold had accepted the King’s pardon, and the port tightened under Charles Vane, Jack Rackham, Anne Bonny, and Mary Read as British ships approached. With escape barred, Whetstone and Drummond began removing crewmen who could identify Teach’s arrangement. Now Whetstone is trying to gather an unfamiliar replacement crew and leave Nassau with Drummond before the blockade closes. The cost is already visible in the empty berths and the bodies his hired intermediaries have failed to hide.

Role in the story

A disguised pirate captain who hires the PCs to gather a crew for the coming fight, while concealing that most of his own crew are already dead. When the moment opens, he means to take the PCs, Drummond, and a few locals aboard and flee.

“A formative season under Teach taught Bonnet that a crew can become a liability the instant it knows too much.”
From their background
Faction
A pirate captain with past ties to the Flying Gang and the Republic of Pirates; currently operating under the alias Captain Thomas Whetstone.

Known connections

Edward Teach, who sent the request to extract Jack Drummond and may know more about Whetstone’s current murders than he admits.
Benjamin Hornigold, an old connection whose rumored pardon has made Whetstone fear that familiar faces may become informants.
Jack Drummond, the man Whetstone was asked to remove from Nassau and his most dangerous witness.
Charles Vane, Jack Rackham, Anne Bonny, and Mary Read, whose control of the port makes escape a matter of timing rather than permission.
Major secret · GM only
Minor secrets · GM only

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