Anna Murray Douglass “Life in Portrait” Contest Authors of the book, Picturing Frederick Douglass, called Douglass the “Most Photographed American of the Nineteenth Century.” Yet, there are only two known images of Anna Murray Douglass, Frederick’s wife, and partner during 44 years of marriage. As a way to honor this great woman during the Centennial of the 19th Amendment, Frederick Douglass Family Initiatives (FDFI) asked Rochester area students to help us imagine how Anna may have looked in portraits during different stages of her life. How does Anna appear in your own creative rendering? Her clothing? Her hair? Her eyes? Her smile? What’s in the background? Black and white or color? Art experts, historians, journalists, and Douglass descendants reviewed all of our entries and selected winners at three levels: elementary, middle, and high school.