Cassandra Webb is a minor antagonist in the second season of Law & Order: Organized Crime. Cassandra is the wife and accomplice of gang leader and drug kingpin, Preston Webb.
Law & Order: Organized Crime
Cassandra gave Congressman Leon Kilbride a tour of the art gallery that she owned before being approached by Webb. Webb then started complimenting Cassandra and Cassandra then left Kilbride and Webb alone to talk about business, knowing that they were talking about their crimes. Later that day, Cassandra and Webb attended a church service led by Derrick Riley who was the sister of undercover detective, Carmen 'Nova' Riley. Cassandra introduced herself to Derrick telling him that she was inspired by him. Derrick then revealed to Cassandra and Webb that Carmen was his sister which surprised Webb.
Cassandra then hosted a fundraiser event at her art gallery which was attended by Webb, Kilbride, Sergeant Ayanna Bell and her wife, Denise. Cassandra welcomed everyone to her art gallery and thanked them for attending this event. Cassandra then started making a few jokes about Webb before letting him speak. Kilbride then introduced Bell and Denise to Cassandra and Webb.
After Webb murdered two rogue gang members, Webb told his newborn grandson about what he did and why he did it. Cassandra then walked in and told Webb to keep the promise that he made to their grandson. That evening, at the Webb home, Carmen and Derrick attended a family dinner with Cassandra, Webb, Webb's daughter and her husband. Cassandra and Webb then found out about Derrick's new charity project and offered to donate money. After they left, Carmen told Derrick not to accept their money because they get it in criminal ways.
After a crate of guns and one of Cassandra's sculptures went missing, Webb called Cassandra while she was giving someone a tour of the art gallery. Webb told Cassandra that one of her sculptures was stolen. Cassandra then started scolding Webb, telling him to fix the mistake he made, Webb then hired Detective Elliot Stabler and Detective Frank Donnelly to find the crate of guns and the missing sculpture.
Stabler approached Cassandra at the art gallery and introduced himself. Cassandra then started showing Stabler around the gallery while talking to him about the missing sculpture. Cassandra then flirted with Stabler, telling them that she knows when a man has good taste. Before Stabler left, Cassandra gave Stabler luck on the search. Later that evening, Stabler gave Webb the box with Cassandra's missing sculpture. Webb then brought it home for Cassandra and Cassandra told him that she knows Stabler found it and that he is a good detective. Cassandra then started calling Donnelly unreliable and that it scares her. Webb then told Cassandra that Donnelly should be scared of her before telling her that he will be right back.
Bell and a police team approached Cassandra at her art gallery while searching for a little girl named Sara Santos. Cassandra became embarrassed by Bell's sudden appearance after everyone at the art gallery started looking at her. After Sara Santos was found, Cassandra approached Webb about Bell raiding her gallery and accused Webb of ignoring her feelings, encouraging him to take proper action. Webb then called Nova after meeting with Cassandra and told her that it's time.
After Preston was found dead at the bottom of a canal, Cassandra went to identify Webb's body and asked to have a few minutes alone with her deceased husband. However, Cassandra was interrupted by Bell and was arrested for Webb's murder, and for ordering the hit on Stabler, by Bell and two other uniformed officers. In the end, the murder charges against Cassandra were dropped but she was still facing other serious charges.