Jerry Abershawe “The Laughing Highwayman”

“Jerry Abershawe: The Fearless Highwayman Who Robbed with a Smile”

• Alias: The Laughing Highwayman
• Gender: Male
• Race: Human
• Occupation: Highwayman, Robber
• Religion: Unknown
• Allies: Members of his gang, fellow outlaws
• Enemies: Law enforcement, authorities
• Abode/Base of operations: Bald-Faced Stag Inn at Putney Vale, Kingston upon Thames
• Nationality: English
• Languages: English
• Alignment: Neutral Evil
• Affiliation(s): His gang of robbers
• Significant others: None mentioned in historical accounts

Jerry Abershawe is a notorious figure known as “The Laughing Highwayman” for his audacious robberies and irreverent demeanor. Born in Kingston upon Thames, Jerry embarked on a life of crime at a young age, leading a gang of robbers who terrorized travelers on the road between Kingston and London. With a quick wit and a charming smile, he embraced the thrill of his illicit activities, leaving his mark on the late eighteenth-century criminal underworld.

Jerry’s motivation stems from a desire for wealth and the thrill of the chase. He saw himself as a modern-day Robin Hood, taking from the rich to provide for himself and his associates. His audacious exploits and daring escapes became the stuff of legends, as he outwitted authorities time and again. With a mischievous grin, Jerry revels in his ability to outsmart his pursuers, always one step ahead in the game of cat and mouse.

But beneath his roguish exterior lies a complex character. Jerry’s life of crime is driven by a need for freedom and a rebellion against the constraints of society. He refuses to conform to the expectations placed upon him, embracing the life of an outlaw with a contagious zest for life. His laughter echoes through the night as he eludes capture, leaving behind a trail of bewildered victims and frustrated lawmen.

While wealth and adventure are at the forefront of Jerry’s pursuits, he harbors a desire for recognition and infamy. His boldness and daring acts have earned him a place in the criminal underworld’s hall of fame. With each robbery, he cements his reputation as a fearless and cunning highwayman, leaving a legacy that will be remembered long after his demise.

Jerry’s ultimate goal is to live life on his own terms, free from the shackles of societal norms and expectations. He seeks adventure, excitement, and a sense of liberation that can only be found on the open road. His laughter is a defiance against the constraints of authority, a reminder that he will not be tamed or silenced.

In the end, Jerry Abershawe’s story is one of audacity, wit, and a relentless pursuit of personal freedom. He laughs in the face of danger, taunting those who seek to bring him down. Whether he is a hero or a villain, one thing is certain – his legend will live on, ensuring that the name Jerry Abershawe will forever be associated with the audacious spirit of the Laughing Highwayman.

Jerry Abershawe, The Laughing Highwayman

Medium humanoid (human), neutral evil

Armor Class 15 (leather armor) Hit Points 82 (15d8 + 15) Speed 30 ft.

STR	DEX	CON	INT	WIS	CHA
14 (+2)	18 (+4)	12 (+1)	13 (+1)	10 (+0)	16 (+3)

Saving Throws Dex +7, Wis +3 Skills Acrobatics +7, Deception +6, Perception +3, Sleight of Hand +7, Stealth +7 Senses passive Perception 13 Languages Common Challenge 5 (1,800 XP)

Actions Rapier. Melee Weapon Attack: +7 to hit, reach 5 ft., one target. Hit: 8 (1d8 + 4) piercing damage.

Pistol Shot. Ranged Weapon Attack: +7 to hit, range 30/90 ft., one target. Hit: 10 (2d6 + 4) piercing damage.

Quick Escape. As a bonus action, Jerry can Disengage or Hide.

Reactions Evasive Maneuvers. When a creature makes a ranged attack against Jerry and misses, he can use his reaction to move up to half his speed without provoking opportunity attacks.

Legendary Actions Jerry can take 2 legendary actions, 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. Jerry regains spent legendary actions at the start of his turn.

Daring Flourish. Jerry makes a Rapier attack.

Distracting Taunt. Jerry taunts a creature within 30 feet, forcing it to make a Wisdom saving throw (DC 14) or have disadvantage on attacks against targets other than Jerry until the start of Jerry’s next turn.

Uncanny Dodge. Jerry uses his reaction to halve the damage from an attack he can see.

Equipment Leather armor, rapier, pistol, lockpicks, disguise kit, 50 gp

Special Abilities Laughing Rogue. Jerry has advantage on Dexterity (Stealth) checks and can add his Charisma modifier to Dexterity (Stealth) checks.

Cunning Action. On each of his turns, Jerry can use a bonus action to take the Dash, Disengage, or Hide action.

Evasion. If Jerry 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.

Infamous Reputation. Jerry has advantage on Charisma (Intimidation) checks when dealing with common folk who know of his criminal reputation.

Description Jerry is a lean and agile figure, dressed in stylish yet practical leather armor. His dark hair is slightly disheveled, and his captivating smile hints at both cunning and charm. He carries a rapier and a loaded pistol, always ready for a quick and deadly strike. His roguish persona is enhanced by a touch of flamboyance, often seen in his confident posture and theatrical gestures.

Backstory Jerry Abershawe, known as “The Laughing Highwayman,” has become a legend throughout the land for his audacious criminal escapades. Born into poverty, he turned to a life of robbery and highwaymanry to survive. His quick wit, daring exploits, and ruthless encounters have earned him a notorious reputation as a fearless and cunning highwayman.

Jerry’s ultimate goal is to accumulate enough wealth and notoriety to retire from his life of crime and live a lavish and carefree existence. He revels in the thrill of outsmarting his enemies and enjoys the attention and admiration he receives from those who appreciate his cunning and charm. However, his notorious deeds have also made him enemies among the law enforcement and rival criminals, who seek to bring him down and claim the bounty on his head.

Roleplaying Tips

• Speak with a confident and playful tone, always ready with a clever quip or witty remark.
• Embrace Jerry’s roguish charm and use your charisma to your advantage in social interactions.
• Showcase Jerry’s quick reflexes and agility in combat, utilizing his evasion abilities to dodge attacks.
• Play up the contrast between Jerry’s lighthearted demeanor and his ruthless efficiency as a highwayman.
• Have Jerry frequently engage in daring stunts and flashy maneuvers, showcasing his skill and showmanship.

Adventure Hooks

• Jerry approaches the party with an intriguing offer: a daring heist that promises great riches but carries considerable risks. He seeks their assistance and promises a generous share of the spoils.
• Themysterious disappearance of valuable artifacts from a local museum has been attributed to Jerry. The party is hired to track him down and retrieve the stolen treasures, navigating the dangerous world of underground criminals and secret hideouts.
• A rumor circulates that Jerry has hidden a legendary treasure in a remote location. The party embarks on a treacherous journey to find the hidden stash before other interested parties, including rival thieves’ guilds, can claim it.
• While on the road, the party encounters Jerry disguised as a traveling entertainer. Intrigued by their skills and reputation, he challenges them to a series of contests and games, testing their mettle and offering rewards for their victories.
• The party becomes entangled in a web of political intrigue, discovering that Jerry is involved in a plot to overthrow a local noble. They must choose whether to align with him and join his cause or work against him to protect the established order.
• A group of victims who have fallen prey to Jerry Abershawe’s robberies seeks revenge and hires the party to track him down. The party must confront the highwayman, navigate the moral complexities of justice and redemption, and decide the fate of the notorious thief.

Currently in the World

Physical Description: Jerry Abershawe is a young man of average height, with a lean and agile build. He has sharp features, including a mischievous smile that earned him the nickname “The Laughing Highwayman.” His dark hair is usually kept slightly unkempt, and his eyes are bright and full of life. Abershawe’s attire consists of a worn leather jacket, sturdy boots, and a wide-brimmed hat, which he wears tilted to one side. He carries a pair of pistols on his belt and a wickedly curved dagger.

Current Situation: Jerry is standing on a moonlit road, surrounded by a dense forest. He is leaning against a tree, his eyes scanning the area with an air of anticipation. His mood is confident and playful, as he awaits the approach of unsuspecting travelers. The sound of rustling leaves and distant horse hooves fills the night, signaling potential victims drawing near. Abershawe smirks, ready to spring into action and carry out his daring robberies with a touch of humor.