| Term | History |
|---|
| 1 | Became a Pirate at age 18 |
| 1 | Is now a Lackey |
| 1 | Arrested |
| 2 | Became a Fixer at age 22 |
| 2 | A guard takes a dislike to you. |
| 3 | Continued as Fixer at age 26 |
| 3 | Offended a prison gang you tried to join. Gain an Enemy. |
| 3 | Promoted to rank 1 |
| 3 | Paroled from prison. |
| 4 | Returned to Pirate at age 30 |
| 4 | Gained a contact. |
| 4 | Promoted to rank 1 |
| 4 | Is now a Henchman |
| 5 | Continued as Pirate at age 34 |
| 5 | Involved in a gambling ring. |
| 5 | Promoted to rank 2 |
| 5 | Is now a Corporal |
| 6 | Continued as Pirate at age 38 |
| 6 | Arrested |
| 7 | Switched to Inmate at age 42 |
| 7 | Injured. |
| 8 | Switched to Thug at age 46 |
| 8 | Accused of assaulting a prison guard. |
| 9 | Continued as Thug at age 50 |
| 9 | Hire a new lawyer. |
| 10 | Aging Crisis. Owe 50,000 for medical bills. |
| 10 | Returned to Inmate at age 54 |
| 10 | Injured. Fully recovered. Owe 5,000 for medical bills. |
| 11 | Returned to Thug at age 58 |
| 11 | Attmped but failed to save a guard or prison officer. |
| 11 | Lightly injured, no permanent damage. Fully recovered. |
| 12 | Aging Crisis. Owe 40,000 for medical bills. |
| 12 | Returned to Inmate at age 62 |
| 12 | A guard takes a dislike to you. |
| 13 | Aging Crisis. Owe 30,000 for medical bills. |
| 13 | Returned to Fixer at age 66 |
| 13 | Accused of assaulting a prison guard. |
| 14 | Aging Crisis. Owe 30,000 for medical bills. |