A legend among Anarchs, the rumors surrounding Smiling Jack are legendary themselves. Some say Jack was a notorious pirate, perhaps even Blackbeard himself. Some say Jack once took over a pack of werewolves by defeating their alpha in hand-to-hand combat. Some say Jack is actually Caine himself cruising around and having a good time before the end times. No matter the truth, Smiling Jack has proven to be a tremendous ally for the Anarch movement and often takes young rabble-rousers under his wing to teach them the ropes and get them pointed in the right direction.

Smiling Jack looks like a combination of a old school biker gang and a pirate. He has a big bushy beard, almost always wears black shades and has tattoos up his arms and around his neck. He has a big boisterous personality, curses constantly, and always has a giant shit-eating grin plastered on his face like everything in the world is joke and he's the only one who sees the punchline.