Robynne is the enigmatic and undisputed head of the Red Cloaks. Born to an elven mother and a human father – both accomplished criminals – she grew up in the shadowed margins of Aranthaes society.
Her parents belonged to a drifting bandit cohort that prowled the outer trade roads, leaving Robynne’s childhood shaped by constant movement, cold camps, and the harsh lessons of survival outside the law.
She was trained in every clandestine skill her parents possessed. Lockpicking, sleight of hand, forgery, knife-work, infiltration, and misdirection were taught to her the way respectable families teach their children to read. She outpaced both parents by adolescence, not merely in skill but in strategic thinking. Where they saw targets, she saw systems.
Robynne
Medium Humanoid (Half-Elf, Rogue: Level 12), Lawful Evil
Hit Points: 84 (12d8+24)
Speed: 30ft., climb 20ft.
14 (+2)
18 (+4)
12 (+1)
16 (+3)
10 (0)
14 (+2)
Skills: Stealth +14, Sleight of Hand +9, Acrobatics +9, Perception +5, Deception +7, Intimidation +9 (with Red Cloak), Thieves’ Tools +9
Damage Resistances: Poison (training and vials)
Condition Immunities: None
Senses: Darkvision 60 ft., Passive Perception 15
Languages: Common, Elvish, Thieves’ Cant
Challenge: 10 Prof Bonus: +4
Special Abilities
Sneak Attack. Once per turn, Robynne deals an extra 28 (8d6) damage on a weapon attack if she has advantage on the attack roll or if an ally is within 5 ft. of the target and is not incapacitated.
Fast Hands. Robynne can use a bonus action to make a Sleight of Hand check, disarm a trap, pick a lock, or use an object.
Second-Story Work. Robynne has a climb speed of 20 ft., and she adds her Dexterity modifier to jump distances instead of Strength.
Uncanny Dodge. When an attacker that Robynne can see hits her with an attack, she can use her reaction to halve the attack’s damage against her.
Evasion. When Robynne is subjected to an effect that allows her to make a Dexterity saving throw to take half damage, she instead takes no damage if she succeeds on the saving throw, and only half damage if she fails.
Reliable Talent. When Robynne makes an ability check that uses a skill she is proficient in, any roll of 9 or lower on the d20 counts as a 10.
Stroke of Luck (1/day). Once per short or long rest, Robynne can turn a missed attack roll into a hit, or a failed saving throw into a success.
Shadow Feint (Recharge 4–6). Robynne targets one creature she can see within 10 ft., using a sudden shift, cloak flourish, or environmental trick. The target must succeed on a DC 16 Wisdom saving throw or Robynne has advantage on all attack rolls against that creature until the end of her next turn.
Actions
Multiattack. Robynne makes two melee or ranged attacks.
Short Sword. Melee Weapon Attack: +9 to hit, reach 5 ft., one target. Hit: 8 (1d6+5) piercing damage, plus 28 (8d6) Sneak Attack damage if applicable.
Poisoned Dagger. Melee or Ranged Weapon Attack: +9 to hit, reach 5 ft. or range 20/60 ft., one target. Hit: 7 (1d4+5) piercing damage plus 10 poison damage, and the target must succeed on a DC 15 Constitution saving throw or be poisoned until the end of its next turn.
Legendary Actions
Robynne can take 1 legendary action, choosing from the options below. Only one legendary action option can be used at a time and only at the end of another creature’s turn. Robynne regains spent legendary actions at the start of her turn.
Command Step. Robynne moves up to half her speed without provoking opportunity attacks.
Quick Blade. Robynne makes one dagger attack.
Equipment
Red Cloak (Magic Item). Grants +1 AC and advantage on Charisma (Intimidation) checks when dealing with Red Cloak members or asserting authority within their territory.
Mask of the Redbreast (Magic Item). While wearing this stylized bird mask, Robynne has advantage on Charisma (Deception) checks made to conceal her identity or motives. Once per long rest she can cast disguise self (self only). As a bonus action, she can issue a sharp command; until the start of her next turn, one allied creature of her choice within 30 ft. that can see or hear her gains a +1 bonus to attack rolls.
Short Sword, Poisoned Daggers, Thieves’ Tools, Poison Vials, Bag of Holding, fine jewelry and valuables.
Tactics
Robynne avoids direct confrontation unless she has overwhelming advantage. She uses Stealth, Shadow Feint, and terrain to secure advantage for Sneak Attack, then withdraws behind her allies. If reduced to half hit points or lower, she focuses on escape, using Command Step and Evasion to break line of sight and vanish.
Robynne’s first claim to notoriety came not through violence, but precision. She began leading a small team of thieves on highly coordinated strikes against merchant caravans – not mere ambushes, but calculated disruptions that exploited gaps in schedules, guard shifts, and terrain. Her approach earned her a reputation for efficiency rather than carnage, though she never balked at brutality when needed.
As her ambitions grew, she absorbed or eliminated rival bands, shaping the once-chaotic Red Cloak bandit brigade into a disciplined force under her banner. By her early twenties, she had established herself as a rising crime lord. By her thirties, she had consolidated every splinter of the Cloaks into a unified syndicate with herself as the sole authority.
Her transformation from highway raider to island-wide kingpin is regarded by scholars (and feared by magistrates) as one of the most rapid and thorough underworld ascensions in recorded Aranthaes history.
The Mask and the Myth
To this day, Robynne never appears publicly without a mask — a sleek, emotionless piece of lacquered wood stylized as a bird’s face and beak. Whether she wears it to conceal identity, to project authority, or as a ritualistic symbol of shedding her former self, none can say. Rumors whisper that she has a network of decoys who wear identical masks, further muddying any attempt to track her movements.
Some believe she is rarely in Draktun at all. Others insist she is always there — and the mask hides more than a face.
Rule and Philosophy
Robynne governs the Red Cloaks with a meticulous and almost bureaucratic ruthlessness.
She is known for her unshakeable internal rules: Loyalty is absolute. Betrayal is the only unforgivable crime. Control the routes, and you control the island. Violence is a tool – not a language.
She tolerates no disorder within her ranks, yet rewards competence and initiative. Many who join her syndicate do so not out of fear, but because life under her system offers more structure and opportunity than life outside it.
To the Red Cloaks, she is not a boss, but the architect of a world where they finally have a place.