So I enjoy writing cool stories about villains in my d&d sessions and I am thinking about writing a book on my Skyrim assassin. The more I play him, the more these interesting story lines about his past begin to pop up. He was once one of the biggest crime lords in the city of Senchal on the southern peninsula of Elsweyr, was a member of the biggest known group of gladiators, pirate lord of the topal seas, duelist, thief, murderer, serial-killer, ya know all that bad stuff.

Its not exactly going to be a "heroic" story aside from a villainous one but it sounds really cool. I might post it in the lore section.
What do you guys think? Sounds pretty cool or lame?
edit: Or I may just make him an anti-hero probably.