Despite earning the highest grade point average (GPA) in her graduating class at the recently integrated Cleveland High School (CHS) in Cleveland, Mississippi, Ms. Jasmine Shepard, an African-American female, was named “co-valedictorian” with Ms. Heather Bouse, a White female, who had a lower GPA. Utilizing Derrick Bell’s rules of racial standing theory and Cheryl Harris’ analytical construct whiteness as property, this article examines Ms. Shepard’s lawsuit against the Cleveland School District. In addition to explaining how White flight was deployed as a policy distraction to justify the inequitable treatment of Ms. Jasmine Shepard, this article posits that the specter of Ms. Shepard becoming Cleveland High School’s first Black valedictorian triggered area Whites’ fear of losing the property value of their whiteness.