This guy is an old DnD character from 4-5 years back, and an old drawing of him from around the same time. He is probably one of my favorite characters and was a real turning point for me in terms of dnd and character design. Due to our party being very large and many people jockeying to be the best combatant, I purposely made him as a skilled thief who always thought on his feet rather than used steel to stay alive. Ever since I played him I have gotten really into the role of the voice of the party and always looking for other ways around situations rather than straight through it with combat.
The campaign ended with him recruiting half of the party as a crew for a pirate ship he had bought.

I am uploading this, both to show what some of my old stuff looked like/ what some of this stuff looks like if I spend lots of time on it, and because he is going to show up in one or two of the next few pictures I am going to upload.