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Kimmy was partnered with Tosha Mitchell as both her lesbian lover and associate in robbing drug dealers until Omar Little returned to Baltimore and then they both joined his crew. Kimmy was adept at infiltrating drug dealing operations using a number of disguises including posing as a nurse to Omar's disabled veteran. Tosha was accidentally killed in a heist gone wrong on a Barksdale stash and Kimmy was distraught. She decides to leave Omar's crew as she believes there are easier people to rob than the Barksdale organization.
In season four Kimmy reunites with Omar in an elaborate plot to steal Proposition Joe's large drug shipment that is meant for him and his Co-Op. After the successful heist, Kimmy takes her cut of the stolen drugs and tells Omar that she will now retire from her dangerous profession.