Oswyn Whispertread

High Raven Oswyn Whispertread

"The trouble with a fair fight is that there is a chance you might lose."

— Oswyn

Physical Description

General Physical Condition

Oswyn is tall and slender, with a wiry build. While he possesses reasonable body strength, he is extremely dexterous and relies more on his speed and reflexes in combat than brute force.

Facial Features

Angular face; short, double-braided beard.

Identifying Characteristics

Duelling scar under his left eye.

Apparel & Accessories

Generally combat-ready in sturdy leather armour, with weapons close at hand, and a few tricks up his sleeve.

Specialized Equipment

Shadowcloak Rapier, +2 (magical)
Shadowcloak Enchanted Studded Leather, +2 (magical)
Daggers x 2
Hand crossbow and quiver with 20 bolts
Vials of forest adder venom x 2 (DC 15, 7d6 poison damage, 1/2 damage on save).
Smoke bomb
Coil of rope with grappling hook.

Mental characteristics

Sexuality

Bi-sexual.

Education

Oswyn was inducted into the Shadowcloaks at an early age, where he was trained in the arts of combat and espionage.

Employment

Oswyn climbed the ranks of the Shadowcloaks slowly and steadily, and after many years of service he holds the rank of High Raven - the organisation's highest position of leadership, reporting directly to Lady Morwen Daggerford herself.

Intellectual Characteristics

A pattern-finder, Oswyn excels at predicting people's future actions based on current and past behaviour. He is an excellent judge of character and is highly skilled at reading people's motivations.

Morality & Philosophy

As a pragmatist, Oswyn understands that it is sometimes necessary for smaller states to fight dirty and break a few laws if they are to avoid the depredations of more powerful nations. While he doesn't revel in the darker tasks of espionage, such as assassination, theft, or blackmail, he will not hesitate to use such tools if he believes that, in doing so, he is safeguarding Daggerford and its citizens.

Personality Characteristics

Motivation

Oswyn loves the complexities of diplomacy, intrigue, and espionage, and gets a thrill from outmanoeuvring opponents with superior strategy.

Likes & Dislikes

Likes games of mental skill; enjoys social interaction; dislikes being the centre of attention.

Virtues & Personality perks

Patient, confident, personable.

Vices & Personality flaws

Finds it difficult to trust anyone completely; has a tendency to lie by omission/withhold information from people unless sharing it is absolutely necessary.

Personality Quirks

Cocks his head to one side and smirks when he witnesses curious or amusing behaviour.

Hygiene

Oswyn's office is kept tidy and organised; the man himself is always clean, if a little scruffy.

Alignment

Chaotic / Good

Gender

Male

Eyes

Dark brown, expressive.

Hair

Shoulder-length, tied back, charcoal black.

Height

6'1"

Weight

165lbs

Oswyn Whispertread

Medium Human Spymaster , Chaotic Good

Armor Class 18

Hit Points 66

Speed 30ft

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STR

10 0

DEX

18 +4

CON

12 +1

INT

15 +2

WIS

13 +1

CHA

16 +3

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Saving Throws Dexterity +7, Intelligence +5

Skills Acrobatics +7, Deception +9, Investigation +9, Perception +4, Persuasion +6, Stealth +10

Senses Passive perception 14

Languages Common, elvish, thieves' cant.

Challenge 8

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Description

Tall, lean, agile, and charming.

Ideals

Greater good: Oswyn believes in safeguarding the good of the people and will do whatever it takes to make sure that those he serves remain safe.

Bonds

Daggerford and its citizens.

Flaws

Oswyn is ruthless in the execution of his duty and will often accept morally questionable choices if he feels that they serve the greater good.

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Cunning Action. On each of his turns, Oswyn can use a bonus action to take the Dash, Disengage, or Hide action.
Evasion. If Oswyn is subjected to an effect that allows him to make a Dexterity saving throw to take only half damage, he instead takes no damage if he succeeds on the saving throw, and only half damage if he fails.
Sneak Attack (1/Turn). Oswyn deals an extra 14 (4d6) damage when he hits a target with a weapon attack and has advantage on the attack roll, or when the target is within 5 feet of an ally that isn’t incapacitated and he doesn’t have disadvantage on the attack roll.

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Actions

Multiattack. Oswyn makes two attacks with his rapier.
Rapier. Melee Weapon Attack: +9 to hit, reach 5 ft., one target. Hit: 11 (1d8 + 6) piercing damage and the target must make a DC 15 Constitution saving throw, taking 24 (7d6) poison damage on a failed save, or half as much damage on a successful one.
Hand Crossbow. Ranged Weapon Attack: +7 to hit, range 30/120 ft., one target. Hit: 7 (1d6 + 4) piercing damage.

Reactions

Protect Me! When a creature Oswyn can see targets him with an attack, he can sidestep behind an ally within 5 feet of it, moving to an unoccupied space within 5 feet of the ally. The chosen ally becomes the target of the attack instead.