James Alexander Chiles

James Alexander Chiles (1860–1930), also known as J. Alexander Chiles, was the first African American lawyer in Lexington, Kentucky. He began his career at the University of Michigan Law School before moving to Lexington to begin his law career. Chiles argued in the United States Supreme Court case Chiles v. Chesapeake & Ohio Railway after being moved from a section of the train reserved from whites only into the colored section, despite having a first class ticket. The case was ultimately dismissed upholding the legality of the Kentucky Separate Coach Law.

Early life James Alexander Chiles was born on June 8, 1860, in Richmond, Virginia.

Legal practice Chiles was the first African American lawyer to practice law in Lexington, Kentucky beginning in 1890. By 1907, Chiles was one of four African American Lawyers in Lexington total.

The "colored" car was established by Kentucky's Separate Coach Law, which stated that black and white train passengers were to ride in separate train cars in 1892. Chiles had claimed that the Separate Coach Law did not apply to him and his interstate commerce laws were being violated. Taking his case to the Circuit Court of Fayette County, Kentucky, Chiles lost his case and was granted no compensation. It was determined that because of Ashland to Lexington, the state could uphold the Separate Coach Law determining that the cars were equal for both black and white passengers with the same conveniences being provided in each and that Chiles must obey the rules and regulations of the railroad company. He requested a new trial, which was denied. In 1907, Chiles appealed the decision taking it to the Kentucky Court of Appeals and won damages to the amount of $100 because of his seat being moved from first class into the unequal colored train car, escorted by a police officer after protest.

Chiles decided to again challenge the decision he was granted claiming violation of separate but equal laws, claiming he was forced to move to an unequal Jim Crow car. Chiles protested that class, not race, should be the determining factor in the law as he had the economic capacity to ride in first class and purchased himself a ticket. Chiles then took the case to the United States Supreme Court where the case was argued April 18, 1910.