"Every time I yank a jawbone from a skull then ram it in an eye socket, I know I'm buildin' a better future." - Smiling Jack.
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 during the Ankaran Plot.