Smiling Jack

Smiling Jack is a Brujah brawler, former pirate, influential Iconoclast, and notable Anarch from the nights of the Anarch Free State. He is considered a legend among young vampires of his clan.

Biography
Rumored to have been a pirate in his mortal years, Smiling Jack is a Tenth Generation Brujah, childe of Mama Lion. A presumably powerful and influential Ancilla during the Final Nights, Smiling Jack is one of the most infamous of all anarchs. His appearance is unassuming - the wild hair and mangy look of a Brujah street bum, but from what has been pieced together, Smiling Jack is a clever planner and a master of the Potence and Celerity Disciplines, favoring them over Presence.

He almost undoubtedly knows many other tricks; however, he seems to eschew the use of manipulative Disciplines such as Dominate or Thaumaturgy. Jack's influence within the Anarch Movement is strong, though he absolutely refuses any formal leadership role. He acts as a mentor and, more importantly, as a friend to many vampires. He seems to have a particular dislike for both the Camarilla in general and the Ventrue in particular. He is not easily provoked into open battle, but his mischievous and under-handed tactics, and his tricks are legendary among young Anarchs.

Smiling Jack is known to enjoy disrupting the Ventrue reign in cities, mostly Embracing indiscriminately, provoking a rise in Caitiff numbers, and even going as far as to thread the events that would ultimately cause the Final Death of Sebastian LaCroix, the Ventrue Prince of Los Angeles in 2004. It's rumored that Smiling Jack is one of the few modern Vampires who've met Caine, in the time in which the latter was posing as a mortal, just before the Time of Judgment during the Final Nights. Smiling Jack became a prophet for Gehenna during the Time of Judgement.

Vampire: The Masquerade - Bloodlines
Smiling Jack is also a supporting character in Vampire: The Masquerade - Bloodlines. He is very friendly to neonates, and will appear early in the game to introduce the player to the World of Darkness and show them the basic abilities of the vampiric condition. During the course of the adventure, he'll be in the Last Round, in Downtown LA, and will offer insight or give his opinion about the events of the game.

Gehenna: The Final Night
It is heavily implied in the novel Gehenna: The Final Night that Smiling Jack meets his Final Death. He is killed by a Nosferatu named Okulos who was disguised as a vampire named Samuel; Jack let himself be killed to ensure that the thin-blood movement he helped start and raise would continue to fulfill Gehenna.

Quotes

 * "Every time I yank a jawbone from a skull and ram it into an eyesocket, I know I'm building a better future." -Smiling Jack
 * "You're a big bad vampire. Hey, great, congrats. Now keep it to yourself."  -Smiling Jack

Character Sheet
Smiling Jack

Sire: Mama Lion

Nature: Bravo

Demeanor: Rebel

Generation: 10th

Embrace: 1654

Apparent Age: Early 40′s

Physical: Strength 5, Dexterity 4, Stamina 5

Social: Charisma 5, Manipulation 4, Appearance 2

Mental: Perception 3, Intelligence 2, Wits 4

Talents: Athletics 4, Brawl 5, Dodge 2, Intimidation 5, Leadership 3, Streetwise 3

Skills: Firearms 3, Melee 5, Stealth 3, Survival 4

Knowledges: Law 1, Linguistics 4, Occult 3

Disciplines: Auspex 2, Celerity 4, Fortitude 4, Potence 5, Presence 3, Thaumaturgy 2

Thaumaturgical Paths: Lure of Flames 1

Backgrounds: Allies 3, Contacts 5, Resources 3, Status 3

Virtues: Conscience 3, Self-Control 1, Courage 5

Morality: Humanity 4

Willpower: 7