Tarence Bailey Sr. is a native of Talbot County, Maryland, and was raised in the Historic Hill Community, the oldest free Black community in the U.S. still in existence today. He is a descendant of both Betsy Bailey, grandmother of Frederick Douglass, and Modesty Green, grandmother of Harriet Tubman.

Bailey has spent most of his career in logistics and transportation and has traveled to every state east of the Mississippi River. In the Bailey family tradition, he also served 10 years in the Maryland National Guard, including a one-year deployment in Kandahar, Afghanistan, with the 115 th Military Police Battalion, First Combat Team, First Armored Brigade. Bailey was involved in several historic missions and was a member of the Guardian Angel detail that provided security to the first generation of female Afghan police officers during their training. He also was selected to operate the battle space control and command vehicle while providing force protection for 1,800 soldiers and civilian personnel.

In February 2021, Bailey established the Bailey-Groce Family Foundation and Operation Frederick Douglass on the Hill. He worked with partners to erect the Frederick Douglass Family Legacy Mural in the Hill Community that details 400-year history of the African American experience in the United States. In his efforts to preserve African American History and Culture, Bailey was instrumental in creating Civil Rights Heroes Day to commemorate the life of Frederick Douglass on Feb. 20. Bailey has been working to build the Grace Brooks Building in The Hill Community to house an African American Cultural Center and the Frederick Douglass Society of African American History, Culture and Affairs.

During his distinguished career, Bailey has received numerous honors and awards. Military awards include Afghanistan Campaign Medal with Campaign Star, Good Conduct Medal, Warrior Leadership Medal, NATO Medal, National Defense Medal, and two State Emergency ribbons. He was named as one of the 101 Men of Distinction of the Eastern Shore and received the Maryland Legacy Award. In 2021, the city of Rochester, NY, celebrated Tarence Bailey Sr. Day.