Chester James worked through the existing political structure to enhance St. Petersburg for African Americans. President Lyndon B. Johnson honored him with a "gold pin" for personally registering to vote more than 1,000 people.

With his wife Rachael, in 1920, they founded the first private elementary school for African American children in St. Petersburg. He focused his energy to improve living conditions in the neighborhood known as Methodist Town, west of 9th Street between Burlington and 4th Avenue North. The city renamed the neighborhood James Town and the two housing projects James Town and James Park were named in honor of his tireless efforts.