Smiling Jack’s origins are shrouded in mystery. He appears as a bearded and bedraggled figure and claims to have been a pirate operating out of the Caribbean in the 1600s CE. Smiling Jack is the definition of an Iconoclast, while his detractors label him an “Anarch Terrorist.” His exploits against tyrannical members of the Camarilla and Sabbat are legendary. There are even rumors that he possesses the unique ability to seemingly switch places with other vampires. Called Smiling Jack's Trick its often the excuse for failed attempts to apprehend him.
Titles and Accolades
He’s known for leaving “Smiling Jack’s Kids” in such locations: newly Embraced Brujah left to be someone else’s problem.
Anarch, Brujah or Ventrue Lore:
- Smiling Jack is known to enjoy disrupting the Ventrue reign in cities, mostly Embracing indiscriminately, provoking a rise in Caitiff numbers
- Had a period of visions that he believed signified Gehenna. He no longer acknowledges this period of his life.