James Alexander Chiles was one of the first African American lawyers to argue a case before the Supreme Court. He was also the first black person to practice law in Lexington, Kentucky.

Chiles was one of eight children, born in 1860 to Richard and Martha Chiles. After completing high school, he attended Lincoln University in Pennsylvania. He later earned a J.D degree from the University of Michigan Law School.
After college, Chiles relocated to Lexington, Kentucky and opened his own law practice. He along with three other black lawyers were the only practicing ones in the city.

In 1910, Chiles took his own case in front of the Supreme Court. He argued against the Chesapeake and Ohio Railroad for desegregation of railroad coaches. While a passenger on the train, Chiles had been forcibly removed to the Colored section despite having purchased a first class ticket from Washington, D.C., to Lexington. Read the courts ruling in J. Alexander Chiles, Plaintiff vs. Chesapeake & Ohio Railway Company (argued April 18, 1910 — decided on May 31, 1910) here.

source:

http://www.pfafoundation.org/wp-content/uploads/2017/02/Notable-SDA-Black-Accomplishments.pdf