The case was ultimately dismissed upholding the legality of the Kentucky Separate Coach Law.
[1] With financial support from his twin brother John, he enrolled at Lincoln University in Chester Co, Pennsylvania in 1882 where he also worked for his board as a dining room waiter.
This was short lived as the following year he moved to Lexington, Kentucky and established his own law firm there.
In 1903, Chiles purchased a first class ticket from Washington D.C. to Lexington, Kentucky on the Chesapeake and Ohio Railroad.
The conductor then asked Chiles to seat himself in the colored section of the train in accordance with the regulations of the O R CO.
He was then forcibly escorted to the colored train car, leading Chiles to challenge this decision as a violation of his Constitutional rights.
Chiles resisted the Kentucky General Assembly when they discussed passing a bill that discriminated against African American voters in 1904.
In 1913, Chiles was appointed as a delegate to the 50th anniversary observance of the Emancipation Proclamation in Philadelphia by Kentucky Governor James McCreary.
He will not stand in the presence of unknown men.” James Alexander Chiles lived a life that serves as an example to all Americans of what is possible when opportunity, access to resources, and hard work are combined”.