Timeline for the The Sinister Three series.
- Things may change overtime as the series progresses.
- Mr. Sinister is born.
- Bob Wilson moves to Stilwater.
- Vanessa Robertson is born.
- Ultor Corporation starts out as a clothing company.
- The 3rd Street Saints are founded.
- The Protagonist is put into a coma.
- Mr. Sinister operates in Stilwater doing hit contracts.
- The Protagonist and Johnny Gat revive the 3rd Street Saints.
- Mr Sinister and Sentient Jack begin plans for the crew, with the backing of Ultor executive Mr. Rollers. The Sinister Three begins its early stages.
- Genkibowl VII is held in Steelport. The filming if Gangstas in Space is announced.
- Jenny Jaros is kidnapped on the set of Gangstas in Space by Mr. Sinister.
- Mr. Sinister and Sentient Jack kidnap Shaundi and Viola during the STAG's occupation of Magarac Island. They blow the statue in order to fool the 3rd Street Saints into thinking both women are dead.
- The Protagonist kills Cyrus Temple to avenge Shaundi and Viola's "deaths", seemingly unaware of the Sinister Three's presence.
- Steelport becomes a City State, with Pierce Washington as Mayor.
- A terrorist threat against the United States leads to The Protagonist to travel to Washington D.C. to meet the President of the United States, and embarks on a dangerous assignment to the Middle East. With lack of Saints leadership in Steelport, the Sinister Three begin to take over their operations.
- Kinzie Kensington attempts to warn the Saints about the impending Zin invasion, but they refuse to listen. Sometime after, she discovers about the Sinister Three. They discover her knowledge and capture her, but playing on her insecurities they offer her a job. Kinzie defects to the Sinister Three, without informing the Saints.
- Taking on board her information about the Zin, Mr. Sinister, Sentient Jack and Kinzie go and visit Zinyak, and sell him information on the Saints but in return for allowing to keep Stilwater and Steeport. Zinyak agrees.
- The Zin launch a surprise invasion on earth, and abduct The Protagonist along with the rest of the Saints at their 3 Count crib.
- Zinyak creates a mock destruction of the earth to fool the Saints. He allows the Sinister Three to operate in Steelport and Stilwater. The Sinister Three find themselves in a war with the remaining Saints.
- Mr. Sinister murders Fun Shaundi and later renames Steelport "Sinister-port". (The Sinister Three Epilogue)
- Cypher begins investigating the Sinister Three.
- Sentinel Jack and Kinzie defect from the Sinister Three.