| 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 | You commit a legendary crime. |
| 2 | Promoted to rank 2 |
| 2 | Is now a Corporal |
| 3 | Continued as Pirate at age 26 |
| 3 | Accused of a crime |
| 3 | Promoted to rank 3 |
| 3 | Is now a Sergeant |
| 4 | Became a Inmate at age 30 |
| 4 | Nearly killed. Fully recovered. Owe 25,000 for medical bills. |
| 5 | Switched to Thug at age 34 |
| 5 | Accused of assaulting a prison guard. |
| 6 | Returned to Inmate at age 38 |
| 6 | You gain a new Rival among the inmates or guards. |
| 7 | Switched to Fixer at age 42 |
| 7 | Vocational Training. |
| 7 | Promoted to rank 1 |
| 8 | Returned to Inmate at age 46 |
| 8 | Hire a new lawyer. |
| 8 | Promoted to rank 1 |
| 8 | Paroled from prison. |
| 9 | Became a Flight at age 50 |
| 9 | Is now a Crewman |
| 9 | Scarred. Fully recovered. Owe 2,500 for medical bills. |
| 10 | Aging Crisis. Owe 10,000 for medical bills. |
| 10 | Retired at age 54 |
| 10 | Gained a contact. |
| 11 | Aging Crisis. Owe 30,000 for medical bills. |
| 11 | Birth or Death involving a family member or close friend. |
| 12 | Aging Crisis. Owe 60,000 for medical bills. |
| 12 | Moved to a new world. |
| 13 | Aging Crisis. Owe 40,000 for medical bills. |
| 13 | A new romantic starts. Gain an Ally. |
| 14 | Aging Crisis. Owe 30,000 for medical bills. |
| 14 | A romantic relationship deepens, possibly leading to marriage. Gain an Ally. |
| 15 | Aging Crisis. Owe 10,000 for medical bills. |