Dean has never been able to keep a job. He's been in and out of jail for charges such as theft, sexual assault, and spousal abuse. Dean would most likely be diagnosed as having:

Dean would most likely be diagnosed as having: antisocial personality.

Explanation:

The diagnose of antisocial personality has to do with a person that doesn't have moral concience, or empathy of any kind with others. This means a person with such diagnose can commit terrible crimes and not feel any guilt.