As the matriarch of her family Tippy Winston is the most powerful piece in the game! With the help of her sons, she's made a plan to reform the hood and make everyone rich, but the plan is threatened when her shady past resurfaces.
| Actor | Role |
|---|---|
 Towanda BraxtonTippy Winston | Tippy Winston |
 Denzell DandridgeMalik Winston | Malik Winston |
 Crystal HughesKarrine | Karrine |
 Teresa CelesteSimone | Simone |
 Alphonso A'Qen-Aten JacksonZilla | Zilla |
| JJocelyn CastorTony | Tony |
 Marquise ClarkCujo | Cujo |
 Brendan GoshaySpike | Spike |
| LLana S. ShieldsSade | Sade |
| KKing JudahMike | Mike |
 Fred GalyeanCongressman Bell | Congressman Bell |
| BBakari BloctonYoung Malik Winston | Young Malik Winston |
| TTy GoudyPastor Clark (credit only) | Pastor Clark (credit only) |
| FFrencheon GriffinBruce | Bruce |
| TTamika MyrieTippy's Assistant | Tippy's Assistant |
| PPiarry OriolCustomer 1 | Customer 1 |