| Term | History |
|---|
| 1 | Became a Pirate at age 18 |
| 1 | Is now a Lackey |
| 1 | Involved in a gambling ring. |
| 1 | Promoted to rank 1 |
| 1 | Is now a Henchman |
| 2 | Continued as Pirate at age 22 |
| 2 | Crime pays off. Gain victim as Enemy. |
| 2 | Promoted to rank 2 |
| 2 | Is now a Corporal |
| 3 | Continued as Pirate at age 26 |
| 3 | Involved in a gambling ring. |
| 3 | Promoted to rank 3 |
| 3 | Is now a Sergeant |
| 4 | Continued as Pirate at age 30 |
| 4 | Arrested |
| 5 | Became a Fixer at age 34 |
| 5 | Accused of assaulting a prison guard. |
| 6 | Switched to Thug at age 38 |
| 6 | Parole hearing. |
| 6 | Promoted to rank 1 |
| 7 | Returned to Fixer at age 42 |
| 7 | A guard takes a dislike to you. |
| 8 | Switched to Inmate at age 46 |
| 8 | Assigned to difficult or backbreaking labour. |
| 8 | Promoted to rank 1 |
| 9 | Returned to Fixer at age 50 |
| 9 | Persecuted by a prison gang. |
| 10 | Returned to Thug at age 54 |
| 10 | Hire a new lawyer. |
| 11 | Aging Crisis. Owe 10,000 for medical bills. |
| 11 | Returned to Inmate at age 58 |
| 11 | Accused of assaulting a prison guard. |
| 12 | Aging Crisis. Owe 30,000 for medical bills. |
| 12 | Returned to Thug at age 62 |
| 12 | Lost eye or limb. Fully recovered. Owe 10,000 for medical bills. |
| 13 | Aging Crisis. Owe 50,000 for medical bills. |
| 13 | Returned to Inmate at age 66 |
| 13 | Good Behaviour. |
| 14 | Aging Crisis. Owe 60,000 for medical bills. |
| 14 | Returned to Thug at age 70 |
| 14 | Nearly killed. Owe 25,000 for medical bills. |
| 15 | Aging Crisis. Owe 60,000 for medical bills. |
| 15 | Returned to Inmate at age 74 |
| 15 | Lost eye or limb. Fully recovered. Owe 10,000 for medical bills. |
| 16 | Aging Crisis. Owe 10,000 for medical bills. |