Caitlin Greenidge's background is explored, noting her family's roots in Barbados and her father's career as an FBI lawyer. The hosts point out the hypocrisy of Greenidge critiquing the FBI's monitoring of Lorraine Hansberry while touting her father's role in the same institution. They argue that her "white shoe lawyer" upbringing places her in a position of privilege that detaches her from the target audience of her writing.