The Thug of my Dreams

[JackMage666]

So, I want to make a Thug style character for a campaign I'm doing. I mostly want a tough rogue, who hits hard and alot. I also want him to be a scoundrel. so I'm useing choice hidden weapons from Complete Scoundrel. The idea of the character is he's prison scum, and spends half his time in, and half his time out. CN, with a heavy emphasis on Chaos.

Any feat/class/prestige class suggestions? I don't have a problem with multiclassing, so that's not a problem. Starting level is 6, but I don't mind planning some stuff ahead of time.

[melchizedek]

Deft Strike (complete adventurer) might come in very useful. Vexing Flank and Adaptable Flank (PHBII) might also come in very handy if you focused on flanking opponents, which would be the best tactic for that type of rogue.

[JackMage666]

I was thinking maybe Avenging Executioner or Streetfighter for the PrC.. With a simple Rogue/Fighter mix for base classes. I wanted to focus on tripping, with Improved Trip and Knock-down, but a better way to get foes to loose their Dex to AC would be useful.