| Term | History |
|---|
| 1 | Became a Enforcer at age 18 |
| 1 | Involved in a feud with a rival criminal organization. |
| 2 | Continued as Enforcer at age 22 |
| 2 | You commit a legendary crime. |
| 2 | Promoted to rank 1 |
| 3 | Continued as Enforcer at age 26 |
| 3 | Lightly injured, no permanent damage. Fully recovered. |
| 4 | Switched to Pirate at age 30 |
| 4 | Is now a Lackey |
| 4 | Accused of a crime |
| 4 | Promoted to rank 1 |
| 4 | Is now a Henchman |
| 5 | Became a Inmate at age 34 |
| 5 | A guard takes a dislike to you. |
| 6 | Switched to Thug at age 38 |
| 6 | Persecuted by a prison gang. |
| 7 | Returned to Inmate at age 42 |
| 7 | Accused of assaulting a prison guard. |
| 8 | Switched to Fixer at age 46 |
| 8 | You gain a new Rival among the inmates or guards. |
| 8 | Promoted to rank 1 |
| 9 | Returned to Inmate at age 50 |
| 9 | Injured. Fully recovered. Owe 5,000 for medical bills. |
| 10 | Returned to Thug at age 54 |
| 10 | Hire a new lawyer. |
| 11 | Continued as Thug at age 58 |
| 11 | Good Behaviour. |
| 11 | Promoted to rank 1 |
| 12 | Returned to Fixer at age 62 |
| 12 | Lost eye or limb. Fully recovered. Owe 10,000 for medical bills. |
| 13 | Aging Crisis. Owe 10,000 for medical bills. |
| 13 | Returned to Thug at age 66 |
| 13 | A riot engulfs the prison. |
| 13 | Loot the guards/other prisoners. |
| 14 | Aging Crisis. Owe 10,000 for medical bills. |
| 14 | Returned to Inmate at age 70 |
| 14 | Hire a new lawyer. |
| 15 | Aging Crisis. Owe 30,000 for medical bills. |