Viola DeWynter and her sister Kiki; after graduating from Harvard Business school, joined the Syndicate instead of working in legitimate business. They mange the Syndicate's finances as well as running the organization's prostitution and human trafficking operations. They are Phillipe Loren's protégées and act as his personal assistants, managing his personal and day-to-day business affairs.
- Viola and Kiki are twins. To differentiate the two, Viola wears white sunglasses while Kiki wears pink ones.
- Viola prefers a calm and calculated approach, whereas Kiki is very hotheaded.
- Early press incorrectly identified the DeWynters as assassins. Lead writer Steve Jaros confirms this is not the case.
- Viola is voiced by former adult film actress Sasha Grey.