Louis Winston (1844-1918) was born in Natchez. He served mainly as a lawyer, but he also served as a police officer and toll collector. He was a prominent Black lawyer in the Natchez and Greenville areas.

Winston founded the Colored Building and Loan Association, which helped finance the purchases of homes for African Americans. He was also the manager of the Mississippi Cooperative and Benefit Association.

The Woodmen of the Union honored Winston as their founder by commissioning the bronze bust on his tombstone. Winston died in 1918. Black artist Isaac Scott Hathaway sculpted the bust. It is listed on the Save Our Sculptures database that the Smithsonian manages.