| Term | History |
|---|
| 1 | Became a Pirate at age 18 |
| 1 | Is now a Lackey |
| 1 | You spend months in the dangerous criminal underworld. |
| 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. |
| 3 | Continued as Pirate at age 26 |
| 3 | A new romantic starts. Gain an Ally. |
| 4 | Continued as Pirate at age 30 |
| 4 | Involved in a feud with a rival criminal organization. |
| 4 | Forced to muster out. |
| 5 | Switched to Enforcer at age 34 |
| 5 | You spend months in the dangerous criminal underworld. |
| 6 | Continued as Enforcer at age 38 |
| 6 | Involved in the planning of an impressive heist. |
| 6 | Promoted to rank 1 |
| 7 | Continued as Enforcer at age 42 |
| 7 | A crime lord considers you his protégé. |
| 7 | Promoted to rank 2 |
| 8 | Continued as Enforcer at age 46 |
| 8 | You commit a legendary crime. |
| 8 | Promoted to rank 3 |
| 9 | Continued as Enforcer at age 50 |
| 9 | Crime pays off. Gain victim as Enemy. |
| 9 | Forced to muster out. |
| 10 | Became a Flight at age 54 |
| 10 | Is now a Crewman |
| 10 | You are blamed for an accident that causes the death of several crew members. Your guilt drives you to excel. |
| 11 | Aging Crisis. Owe 60,000 for medical bills. |
| 11 | Retired at age 58 |
| 11 | Birth or Death involving a family member or close friend. |
| 12 | Aging Crisis. Owe 50,000 for medical bills. |
| 12 | Victim of a crime |
| 13 | Aging Crisis. Owe 60,000 for medical bills. |
| 13 | Betrayal. Convert an Ally into a Rival or Enemy. |
| 14 | Aging Crisis. Owe 60,000 for medical bills. |