While serving in the Massachusetts House of Representatives in 1965, he sponsored the state's Racial Imbalance Act, which led to the desegregation of Boston's public schools.

Bolling was a decorated World War II veteran, earning a Silver Star as a member of the segregated "Buffalo Soldiers" 92nd infantry division.

He first showed a talent for politics when he ran for president of his predominantly white Framingham High School class and obtained endorsements from Massachusetts governor Leverett Saltonstall and Boston Mayor James Michael Curley.

[1][2][3] He attended Howard University for a time, performing as a tap dancer in D.C.-area nightclubs to earn money for tuition,[1] before leaving school to join the military.

[2] In 1963, he proposed the original Racial Imbalance Act, a version of which was signed into law by Governor John Volpe in 1965 and which led to the desegregation of Boston's public schools.

Widely recognized for his diplomatic skills, Bolling was chairman of the Special Legislative Committee on Foreign Trade and was hosted by heads of state around the world.