Rollins administrators and faculty maintained close connections with leading black educational institutions in the state, like Bethune-Cookman University and the Hungerford Vocational School of Eatonville.

Mary McLeod Bethune (1875-1955) was a celebrated early African American educator and the founder of Bethune-Cookman College (founded in 1904), a still successful HBCU located in nearby Daytona, Florida. After being denied access to speak at Rollins in the 1930s, Mary later (in 1949) became the first black women in U.S. history to be given an honorary degree by a white, southern college. This is a picture of her and Rollins College President Hamilton Holt (1872-1951) after the ceremony wherein she received her historic award.

President Holt (who served as president from 1925 to 1949) was an unusually progressive influence on Rollins and the town of Winter Park. He was a vocal race relations advocate and a founding member of the NAACP. Over the years a professional friendship blossomed between Holt and Bethune, and as a result a strong alliance formed between Rollins College and Bethune-Cookman College. This connection would last for decades, even after both of their deaths. The administration at Rollins and Bethune-Cookman continued to work together to advance the experience of black students, black educators, and black studies as a curriculum even through the 1970s.

— Marisa Lagos (Class of 2019)