Convict
You have done time. Quite a lot of time, in fact; enough to fully acclimate to the life of a prisoner, whether you deserv ed it or not. Your time incarcerated has shaped you as an individual and it is highly unlikely that you bear much resemblance to the person you were before you went inside.
What was your supposed crime? Were you innocent, guilty, or something in between? Has your time in custody made you vengeful? Cynical? Traumatized? Merciful? Determined to make the most or your freedom? How do you feel about the prospect of going back inside? How do you view your current freedom? Were you released, or did you escape?
Traveler’s clothes, crowbar, dagger.
Incarceration affects different people differently. Choose one of the following options.
Hardened Reputation. You gain an expertise die on Intimidation checks against other former prisoners, criminals, and others who know how tough those who have served time can be.
Cell-Dwelling Scholar. You spent your time locked up reading anything you could get your hands on, but had a particular interest that you studied over all others. You gain a skill specialty of your choice from either Arcana, Culture, Engineering, History, Nature, or Religion.
You may occasionally meet someone you knew from your time as a prisoner or one of the parties who put you there. They will be interested to see how you are using your freedom. Depending on how you play your cards, you may acquire the services of up to 8 bandits who may form the start of a new gang or an organization devoted to something less nefarious, depending on the example you set.