Robert A. Sengstacke was born in Chicago to the family that founded the influential African American newspaper, the Chicago Defender. The Defender played a key role in promoting civil rights and supporting the Great Migration.

Sengstacke developed an interest in photography during his teenage years, recording images of everyday life in his neighborhood. He later pursued a career as a photojournalist, capturing pivotal moments of the 1960s. Sengstacke worked as both a photographer and editor at the Defender.

In 1966 he worked as a photographer for Muhammad Speaks, the newspaper of the Nation of Islam, documenting their activities. He photographed iconic figures such as Muhammad Ali, Jesse Jackson, and Dr. Martin Luther King Jr., and his work was featured in Ebony, Life, Downbeat, and Look magazines.