Jessie Benjamin Gladden was born on December 11, 1930 in New York City. Her mother was a domestic and later a business owner and her father was a laborer. In 1948, Gladden earned her high school diploma from North Hampton County Training School in North Carolina. In 1953, she earned her bachelor’s of science degree in social science and English from North Carolina Agriculture and Technology. Gladden began her teaching career in 1956 at Charles Hamilton Houston elementary school in Baltimore From 1970 until 1971, Gladden traded in her chalk and eraser for a camera and studio audience when she taught for the show Newslab that aired on Maryland Public Television. In 1973, she earned her master’s degree in American history from Morgan State University.
Gladden’s master’s thesis highlighted the medical accomplishments of Morgan State University medical scientist, Vivien Thomas. Thomas, with only a high school education, developed many surgical techniques and instruments used in treating and identifying diseases. Gladden’s thesis was titled, Vivien Thomas: Black Non-Doctor. From 1977 until 1992, she worked as a supervisor, Division of Social Studies curriculum, for Baltimore City Schools. She retired from the Baltimore City School system in 1992. The following year, she took a position as a teacher supervisor at Johns Hopkins University until her retirement in 2001.