Captain Macheath, the Swashbuckling Scoundrel

“Charming Rogue or Ruthless Criminal? Meet Captain Macheath – the Legendary Highwayman!”

• Alias: Captain Macheath, Mack the Knife
• Gender: Male
• Race: Human
• Occupation: Highwayman, Robber, Outlaw
• Religion: Irreligious
• Allies: The Gang of Outlaws, Polly Peachum
• Enemies: The Law, Tiger Brown, Jonathan Jeremiah Peachum
• Abode/Base of Operations: Secret hideout in the wilderness
• Nationality: English
• Languages: English, Thieves’ Cant
• Alignment: Chaotic Neutral
• Affiliation(s): Criminal underworld, Gang of Outlaws
• Significant Others: Polly Peachum

Captain Macheath, a charismatic and enigmatic figure, lives life on the edge of law and order. He is a daring highwayman who roams the treacherous highways and shadowy alleys of the realm. Known for his dashing looks and undeniable charm, he is a master of disguise, easily blending into both high society and the criminal underworld.

Macheath fears the monotony of a conventional life and the constraints of authority. He thrives on the thrill of danger and the adrenaline rush that comes with his illicit activities. Born into poverty, he has a burning desire for wealth and status, which drives him to commit daring robberies and engage in criminal enterprises.

What motivates Captain Macheath is not just personal gain; he yearns to challenge the oppressive structures of society. He wants to redistribute wealth from the corrupt and the powerful to the downtrodden and oppressed. Macheath believes he is a symbol of defiance against a system that favors the rich and exploits the poor.

With a heart that sways between roguish charm and righteous rebellion, Captain Macheath is a complex character who navigates the blurred lines of morality in pursuit of his own version of justice.

Captain Macheath

Medium humanoid (human), neutral

Armor Class 16 (leather armor) Hit Points 126 (12d12 + 48) Speed 30 ft.

STR	DEX	CON	INT	WIS	CHA
12 (+1)	18 (+4)	18 (+4)	16 (+3)	14 (+2)	20 (+5)

Skills: Acrobatics +8, Deception +9, Persuasion +9, Sleight of Hand +8

Senses: Passive Perception 12

Languages: English, Thieves’ Cant

Challenge: 8 (3,900 XP)

Background: Charlatan

Class: Swashbuckler Rogue 12

Special Traits:

• Evasion. If Captain Macheath is subjected to an effect that allows him to make a Dexterity saving throw to take only half damage, he instead takes no damage on a success and half damage on a failure.
• Fancy Footwork. After making a melee attack against a creature, Captain Macheath doesn’t provoke opportunity attacks from that creature for the rest of his turn.
• Swashbuckler’s Fancy. Captain Macheath can add his Charisma modifier to his initiative rolls.
• Panache. Captain Macheath can use Charisma instead of Intelligence for investigation and persuasion checks.
• Elegant Maneuver. Captain Macheath can use a bonus action to make a Charisma (Persuasion) check contested by a creature’s Wisdom (Insight) check. If he succeeds, the target is charmed by him for 1 minute.
• Sneak Attack (2/Turn). Captain Macheath deals an extra 4d6 damage when he hits a target with a weapon attack and has advantage on the attack roll or when an ally is within 5 feet of the target. He doesn’t need advantage on the attack roll if he has no disadvantage.
• Evasion Mastery. Captain Macheath gains the benefits of the Evasion trait as long as he is in his lair.

Actions:

• Multiattack. Captain Macheath makes two attacks with his rapier.
• Rapier. Melee Weapon Attack: +8 to hit, reach 5 ft., one target. Hit: 10 (1d8 + 4) piercing damage.
• Flourish. Captain Macheath can expend one use of his Elegant Maneuver to add 1d10 to the damage roll of a successful rapier attack and to give his target disadvantage on saving throws against his Panache ability for 1 minute.
• Disarming Strike. When Captain Macheath hits a creature with a melee attack, he can expend one use of his Elegant Maneuver to attempt to disarm the target, forcing it to make a DC 16 Strength saving throw. On a failed save, the target drops one item it is holding of Captain Macheath’s choice.
• Evasion Mastery (Recharge 5-6). Captain Macheath can use this ability to take the Dodge action as a reaction when targeted by an attack.

Equipment:

• Leather armor
• Rapier
• Thieves’ tools
• A set of fine clothes
• A disguise kit
• A forgery kit
• 50 gp

Lair Actions:

• Captain Macheath’s lair is a hidden and luxurious hideout in the heart of the city. While in his lair, he can take lair actions. On initiative count 20 (losing initiative ties), Captain Macheath takes a lair action to cause one of the following effects; he can’t use the same effect two rounds in a row:
  • Distracting Performance. Captain Macheath dazzles his foes with a mesmerizing performance, forcing all creatures within 60 feet to make a DC 16 Wisdom saving throw or be charmed for 1 minute.
  • Sudden Escape. Captain Macheath uses his Fancy Footwork ability as a bonus action, allowing him to move away from any creatures he has attacked this turn without provoking opportunity attacks.
  • Smooth Talk. Captain Macheath can use his Panache ability on one creature within 60 feet, even if he doesn’t share a language with the target.

Reactions:

• Evasion. When Captain Macheath is subjected to an effect that allows him to make a Dexterity saving throw to take only half damage, he instead takes no damage on a success and half damage on a failure.
• Uncanny Dodge. When an attacker that Captain Macheath can see hits him with an attack, he can use his reaction to halve the attack’s damage against him.

CR Level: 8

Captain Macheath is a charming and cunning rogue, famous for his swashbuckling style and ability to outwit his foes. He is a master of persuasion and deception, and his rapier skills are unparalleled. While not an inherently evil character, his actions often fall on the wrong side of the law, making him a formidable opponent for any adventuring party.

Currently in the World

Captain Macheath is a tall and imposing figure, standing at about 6 feet with a lean, athletic build. He has dark, wavy hair that falls slightly over his forehead, giving him a roguish and charming appearance. His piercing blue eyes seem to hold a hint of mischief and danger, reflecting a life of lawlessness and adventure.

He is currently dressed in a dashing ensemble befitting his reputation as a highwayman. His attire consists of a deep crimson coat with gold embroidery, worn open to reveal a ruffled white shirt. He wears fitted black trousers tucked into knee-high leather boots adorned with silver buckles. Around his waist, a wide leather belt secures a pair of ornate, silver-handled flintlock pistols, a testament to his proficiency with firearms.

Macheath leans casually against a moss-covered stone wall in a dimly lit alley, his boots kicking up small pebbles as he surveys his surroundings. The alley is a maze of winding cobblestone streets and flickering lanterns, providing the perfect cover for his illicit activities. The distant sounds of a bustling city can be heard, but in this hidden corner, he remains hidden from prying eyes.

His mood is one of calculated confidence, as he plans his next daring heist. Macheath is always on the lookout for opportunities to outsmart the law and make a quick profit, his charismatic grin never far from his lips.