| Term | History |
| 1 | Became a Pirate at age 18 |
| 1 | Is now a Lackey |
| 1 | Involved in the planning of an impressive heist. |
| 1 | Promoted to rank 1 |
| 1 | Is now a Henchman |
| 2 | Continued as Pirate at age 22 |
| 2 | Refuse to backstab a fellow rogue for personal gain. Gain an Ally |
| 2 | Promoted to rank 2 |
| 2 | Is now a Corporal |
| 3 | Continued as Pirate at age 26 |
| 3 | Backstab a fellow rogue for personal gain. |
| 3 | Promoted to rank 3 |
| 3 | Is now a Sergeant |
| 4 | Continued as Pirate at age 30 |
| 4 | Involved in a feud with a rival criminal organization. |
| 4 | Injured. Fully recovered. Owe 2,500 for medical bills. |
| 4 | Promoted to rank 4 |
| 4 | Is now a Lieutenant |
| 5 | Continued as Pirate at age 34 |
| 5 | A crime lord considers you his protégé. |
| 5 | Promoted to rank 5 |
| 5 | Is now a Leader |
| 6 | Continued as Pirate at age 38 |
| 6 | Refuse to backstab a fellow rogue for personal gain. Gain an Ally |
| 6 | Promoted to rank 6 |
| 6 | Is now a Captain |
| 6 | Forced to muster out. |
| 7 | Became a Barbarian at age 42 |
| 7 | Nearly killed. Fully recovered. Owe 22,500 for medical bills. |
| 8 | Became a Performer at age 46 |
| 8 | Victim of a crime |
| 8 | Forced to continue current assignment |
| 8 | Promoted to rank 1 |
| 9 | Continued as Performer at age 50 |
| 9 | You are forced out because of censorship or controversy. What truth did you get too close to? |
| 10 | Aging Crisis. Owe 30,000 for medical bills. |
| 10 | Retired at age 54 |
| 10 | A new romantic starts. Gain an Ally. |
| 11 | Aging Crisis. Owe 30,000 for medical bills. |
| 11 | Gained a contact. |
| 12 | Aging Crisis. Owe 60,000 for medical bills. |
| 12 | Amnesia. |
| 13 | Aging Crisis. Owe 30,000 for medical bills. |
| 13 | Birth or Death involving a family member or close friend. |
| 14 | Aging Crisis. Owe 60,000 for medical bills. |