Kiki Dewynter and her sister Viola; 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.
- Kiki and Viola are twins. To differentiate the two, Kiki wears pink sunglasses while Viola wears white ones.
- Kiki is very hotheaded whereas Viola prefers a calm, calculated approach.
- Early press incorrectly identified the DeWynters as assassins. Lead writer Steve Jaros confirms this is not the case.
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