| Term | History |
|---|
| 1 | Became a Wanderer at age 18 |
| 1 | Betrayed by a friend. One of your Contacts or Allies betrays you, ending your career. That Contact or Ally becomes a Rival or Enemy. |
| 2 | Became a Enforcer at age 22 |
| 2 | Involved in a feud with a rival criminal organization. |
| 2 | Severely injured. Owe 20,000 for medical bills. |
| 3 | Voluntarily left Enforcer |
| 3 | Switched to Pirate at age 26 |
| 3 | Is now a Lackey |
| 3 | You spend months in the dangerous criminal underworld. |
| 3 | Promoted to rank 1 |
| 3 | Is now a Henchman |
| 4 | Continued as Pirate at age 30 |
| 4 | Backstab a fellow rogue for personal gain. |
| 4 | Promoted to rank 2 |
| 4 | Is now a Corporal |
| 5 | Continued as Pirate at age 34 |
| 5 | A new romantic starts. Gain an Ally. |
| 5 | Promoted to rank 3 |
| 5 | Is now a Sergeant |
| 6 | Continued as Pirate at age 38 |
| 6 | Birth or Death involving a family member or close friend. |
| 6 | Promoted to rank 4 |
| 6 | Is now a Lieutenant |
| 7 | Continued as Pirate at age 42 |
| 7 | Betrayal. Convert an Ally into a Rival or Enemy. |
| 7 | Promoted to rank 5 |
| 7 | Is now a Leader |
| 8 | Continued as Pirate at age 46 |
| 8 | Moved to a new world. |
| 8 | Promoted to rank 6 |
| 8 | Is now a Captain |
| 9 | Continued as Pirate at age 50 |
| 9 | Arrested |
| 10 | Became a Inmate at age 54 |
| 10 | A guard takes a dislike to you. |
| 11 | Aging Crisis. Owe 50,000 for medical bills. |
| 11 | Switched to Thug at age 58 |
| 11 | Nearly killed. Fully recovered. Owe 25,000 for medical bills. |
| 12 | Aging Crisis. Owe 40,000 for medical bills. |
| 12 | Returned to Inmate at age 62 |
| 12 | Special Duty. |
| 13 | Aging Crisis. Owe 60,000 for medical bills. |
| 13 | Switched to Fixer at age 66 |
| 13 | A guard takes a dislike to you. |
| 14 | Aging Crisis. Owe 10,000 for medical bills. |
| 14 | Returned to Inmate at age 70 |
| 14 | Persecuted by a prison gang. |
| 15 | Aging Crisis. Owe 60,000 for medical bills. |