| Term | History |
|---|
| 1 | Became a Pirate at age 18 |
| 1 | Is now a Lackey |
| 1 | Involved in a gambling ring. |
| 2 | Continued as Pirate at age 22 |
| 2 | Arrested |
| 3 | Became a Fixer at age 26 |
| 3 | Vocational Training. |
| 4 | Switched to Inmate at age 30 |
| 4 | Saved a guard or prison officer. Gain an Ally. |
| 4 | Promoted to rank 1 |
| 5 | Continued as Inmate at age 34 |
| 5 | Scarred. Owe 5,000 for medical bills. |
| 6 | Continued as Inmate at age 38 |
| 6 | Hire a new lawyer. |
| 7 | Returned to Fixer at age 42 |
| 7 | Accused of assaulting a prison guard. |
| 8 | Continued as Fixer at age 46 |
| 8 | Injured. Fully recovered. Owe 5,000 for medical bills. |
| 9 | Continued as Fixer at age 50 |
| 9 | Severely injured. Fully recovered. Owe 25,000 for medical bills. |
| 10 | Switched to Thug at age 54 |
| 10 | Special Duty. |
| 11 | Continued as Thug at age 58 |
| 11 | Make friends with another inmate; gain them as a Contact. |
| 12 | Continued as Thug at age 62 |
| 12 | Hire a new lawyer. |
| 13 | Aging Crisis. Owe 40,000 for medical bills. |
| 13 | Continued as Thug at age 66 |
| 13 | Persecuted by a prison gang. |
| 14 | Aging Crisis. Owe 10,000 for medical bills. |
| 14 | Continued as Thug at age 70 |
| 14 | Joined a prison gang |
| 14 | Promoted to rank 1 |
| 15 | Aging Crisis. Owe 30,000 for medical bills. |
| 15 | Returned to Inmate at age 74 |
| 15 | Accused of assaulting a prison guard. |
| 16 | Aging Crisis. Owe 40,000 for medical bills. |