| Term | History |
|---|
| 1 | Became a Pirate at age 18 |
| 1 | Is now a Lackey |
| 1 | A crime lord considers you his protégé. |
| 1 | Promoted to rank 1 |
| 1 | Is now a Henchman |
| 2 | Continued as Pirate at age 22 |
| 2 | A police detective or rival criminal forces you to flee and vows to hunt you down. Gain an Enemy. |
| 3 | Became a Engineer/Gunner at age 26 |
| 3 | Is now a Crewman |
| 3 | You are tormented by or quarrel with an officer or fellow crewman. Gain that character as a Rival. |
| 4 | Returned to Pirate at age 30 |
| 4 | Involved in a feud with a rival criminal organization. |
| 4 | Promoted to rank 2 |
| 4 | Is now a Corporal |
| 5 | Continued as Pirate at age 34 |
| 5 | Arrested |
| 5 | Promoted to rank 3 |
| 5 | Is now a Sergeant |
| 6 | Became a Fixer at age 38 |
| 6 | A guard takes a dislike to you. |
| 7 | Continued as Fixer at age 42 |
| 7 | A guard takes a dislike to you. |
| 8 | Aging Crisis. Owe 10,000 for medical bills. |
| 8 | Switched to Thug at age 46 |
| 8 | A guard takes a dislike to you. |
| 9 | Aging Crisis. Owe 40,000 for medical bills. |
| 9 | Returned to Fixer at age 50 |
| 9 | A guard takes a dislike to you. |
| 10 | Aging Crisis. Owe 40,000 for medical bills. |
| 10 | Continued as Fixer at age 54 |
| 10 | A guard takes a dislike to you. |
| 11 | Aging Crisis. Owe 20,000 for medical bills. |
| 11 | Returned to Thug at age 58 |
| 11 | Persecuted by a prison gang. |
| 12 | Aging Crisis. Owe 30,000 for medical bills. |
| 12 | Continued as Thug at age 62 |
| 12 | A guard takes a dislike to you. |
| 12 | Promoted to rank 1 |
| 13 | Aging Crisis. Owe 20,000 for medical bills. |
| 13 | Switched to Inmate at age 66 |
| 13 | Parole hearing. |
| 14 | Aging Crisis. Owe 50,000 for medical bills. |