Frank James: The Outlaw Enigma

“Meet the Notorious Outlaw Turned Community Leader – Frank James’ Untold Story!”

• Alias: Frank James, Frank “Bud” James
• Gender: Male
• Race: Human
• Occupation: Outlaw, Guerrilla Fighter, farmer
• Religion: Not widely known
• Allies: Jesse James, Cole Younger, other members of the James-Younger Gang, Quantrill’s Raiders
• Enemies: Law enforcement, Pinkerton detectives, rival outlaw gangs
• Abode/Base of Operations: Various hideouts in Missouri, Kentucky, and other states
• Nationality: American
• Languages: English
• Alignment: Chaotic Neutral
• Affiliation(s): James-Younger Gang
• Significant Others: Ann Rutledge (common-law wife)

Frank James, a complex figure of the Old West, emerges as a character shrouded in notoriety. Born into a turbulent era, Frank navigates life’s treacherous waters with an air of stoic determination. Fearless in the face of danger, he finds himself driven by a tumultuous mix of loyalty, vengeance, and survival.

This enigmatic character, born to a troubled legacy, fears being confined by the very history that shaped him. Raised in a time of lawlessness and injustice, Frank stands as a symbol of resilience, torn between avenging his family’s losses and carving a better future. His desires oscillate between reclaiming his tarnished family name and seeking redemption for his past deeds, striving for a life less defined by violence and more by righteousness.

Frank James

Medium humanoid (human), Chaotic Neutral

Armor Class 15 (Outlaw’s Duster) Hit Points 84 (12d8 + 24) Speed 30 ft.

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

Skills Perception +2, Persuasion +5, Stealth +5 Senses passive Perception 12 Languages English Challenge 6 (2,300 XP)

Background: Outlaw

Actions Multiattack. Frank James makes two revolver attacks.

• Revolver. Ranged Weapon Attack: +6 to hit, range 40/120 ft., one target. Hit: 13 (2d8 + 3) piercing damage.
• Quick Draw. Once per turn, when Frank rolls for initiative, he can draw and fire a revolver as a reaction.
• Trick Shot. Frank can spend 1 grit point to perform a trick shot. He makes a revolver attack with disadvantage. If the attack hits, it deals an extra 13 (2d8 + 3) piercing damage and has one of the following effects (Frank’s choice):
  • Deadeye Shot: The target makes a DC 15 Constitution saving throw or is stunned until the end of its next turn.
  • Ricochet Shot: The bullet can hit a second target within 30 feet of the first. Frank makes another attack roll with disadvantage against the second target.
  • Disarming Shot: The target makes a DC 15 Strength saving throw or drops one held item or weapon.

Reactions Dodge. When Frank is targeted by an attack he can see, he can use his reaction to impose disadvantage on the attack roll.

Legendary Actions Frank James 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. Frank regains spent legendary actions at the start of his turn.

Shoot. Frank makes one revolver attack.

Frightening Presence (Costs 2 Actions). Frank forces each creature of his choice within 30 feet that can see him to make a DC 15 Wisdom saving throw or become frightened for 1 minute. A creature can repeat the saving throw at the end of each of its turns, ending the effect on itself on a success.

Frank James’ Equipment

• Horse
• Two Revolvers (loaded with 12 bullets each)
• Studded Leather Armor
• Sheriff’s Badge (non-magical, but a symbol of authority)
• Saddlebag with provisions
• Wanted Poster with a 500 gold piece reward

Abilities Grit (6/Day). Frank has a pool of grit points, which he can expend to perform special actions (Trick Shots). He regains all expended grit points after a short or long rest.

Cunning Action. Frank can take a bonus action on each of his turns in combat to take the Dash, Disengage, or Hide action.

Evasion. When Frank is subjected to an effect that allows him to make a Dexterity saving throw to take half damage on a success, he takes no damage on a success and half damage on a failure.

Uncanny Dodge. When an attacker he can see hits him with an attack, he can use his reaction to halve the attack’s damage against him.

Description Frank James is a tall, rugged man in his early forties with piercing eyes and a perpetual five o’clock shadow. He wears a worn duster coat, a cowboy hat, and carries two gleaming revolvers on his hips. Frank’s demeanor is calm and enigmatic, his past shrouded in mystery. He is known for his lightning-fast draw and unerring accuracy with his revolvers.

Personality Frank is a man of few words, often choosing actions over speech. He is motivated by a desire for freedom and justice, fighting against those who exploit the innocent. Frank fears losing his moral compass and becoming an outlaw without a cause. He aims to protect the weak and bring notorious criminals to justice.

Roleplaying Tips

• Frank is a master of firearms and tactics. He excels in ranged combat and can outdraw most opponents.
• He has a soft spot for those in need and will go to great lengths to help them.
• Frank’s wanted status makes him cautious, and he avoids unnecessary confrontations with the law.

Adventure Hook The party encounters Frank James in a dusty frontier town, where he seeks their help to bring down a corrupt sheriff and a gang of outlaws terrorizing the locals. He offers them a share of the reward money for capturing the gang leader alive, setting the stage for a high-stakes showdown in the Wild West.

Currently in the World

Frank James stands at an average height with a sturdy, well-built frame, reflecting his life on the rugged frontier. He sports a beard, commonly seen among men of his era, and his brown hair, once neatly combed, now appears tousled due to his rough lifestyle. Frank’s piercing blue eyes hold a mix of weariness and vigilance, a testament to his life on the run.

Currently, Frank James wears a worn but functional attire: faded blue jeans, a brown leather vest over a simple cotton shirt, and a battered cowboy hat that shields his face from the harsh sun. His outfit is well-worn and dusty, revealing the hardships of his fugitive existence. A pair of well-used, scuffed boots protect his feet as he navigates the unforgiving terrain.

Frank is crouched behind a large, weathered boulder, surveying the wild surroundings of the Missouri wilderness. Tall grasses sway in the breeze, and the distant murmur of a creek provides a soothing backdrop to his cautious watch. His mood is one of constant alertness, for he knows that danger can lurk around any corner in this lawless land.