| Term | History |
| 1 | Became a Pirate at age 18 |
| 1 | Is now a Lackey |
| 1 | Involved in a feud with a rival criminal organization. |
| 1 | Injured. Fully recovered. Owe 5,000 for medical bills. |
| 1 | Promoted to rank 1 |
| 1 | Is now a Henchman |
| 2 | Continued as Pirate at age 22 |
| 2 | A romantic relationship deepens, possibly leading to marriage. Gain an Ally. |
| 2 | Promoted to rank 2 |
| 2 | Is now a Corporal |
| 3 | Continued as Pirate at age 26 |
| 3 | Refuse to backstab a fellow rogue for personal gain. Gain an Ally |
| 3 | Promoted to rank 3 |
| 3 | Is now a Sergeant |
| 4 | Continued as Pirate at age 30 |
| 4 | You commit a legendary crime. |
| 4 | Promoted to rank 4 |
| 4 | Is now a Lieutenant |
| 5 | Continued as Pirate at age 34 |
| 5 | Involved in the planning of an impressive heist. |
| 5 | Forced to muster out. |
| 6 | Became a Journalist at age 38 |
| 6 | Gain a patron in the arts. Gain an Ally |
| 6 | Promoted to rank 1 |
| 6 | Is now a Freelancer |
| 7 | Continued as Journalist at age 42 |
| 7 | Injured. Fully recovered. Owe 1,250 for medical bills. |
| 8 | Became a Worker at age 46 |
| 8 | Nearly killed. Fully recovered. Owe 12,500 for medical bills. |
| 9 | Aging Crisis. Owe 30,000 for medical bills. |
| 9 | Retired at age 50 |
| 9 | Gained a contact. |
| 10 | Aging Crisis. Owe 10,000 for medical bills. |
| 10 | Betrayal. Convert an Ally into a Rival or Enemy. |
| 11 | Aging Crisis. Owe 60,000 for medical bills. |
| 11 | Gained a contact. |
| 12 | Aging Crisis. Owe 10,000 for medical bills. |
| 12 | Betrayal. Convert an Ally into a Rival or Enemy. |
| 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 40,000 for medical bills. |