Economic impact
Founded Liberty Life Insurance Company in Chicago in 1919, capitalizing it with investments drawn from the Bronzeville community. The company offered life insurance policies to Black Chicagoans at a time when most major white-owned insurers either refused Black applicants or charged them actuarially discriminatory premium rates. Liberty Life merged with two other Black-owned insurance companies in 1929 to form Supreme Liberty Life Insurance Company, one of the largest Black-owned corporations in the United States by the 1940s, with assets exceeding US$40 million at its mid-century peak. Supreme Liberty Life employed hundreds of Black professionals in underwriting, sales, and administration; John H. Johnson, the future founder of Johnson Publishing Company and Ebony magazine, was employed there as a clerk in the early 1940s. Gillespie died in 1925, six years after the company's founding.