This was for Conceptart's weekly character challenge, to create at least two of the four Jacks from playing card lore.

I went a modern route, and tried to tie the weapons and clothing to their symbol in a subtle way. Since diamonds have sharp edges like a knife I chose that for the Jack of Diamond's weapon of choice. The club Jack was easier, and I love the British billy-club. I also thought I'd throw in 3 clubs on his chain... because he hates the sight of blood and as he executes three disciplinary beatings for punishments or interrogations he will trade out each club so he doesn't have to hold a bloody one after each strike. The scratches on his arm are from his victims, as they plead for their lives.