Thomas Boles began his career in public service as a teacher before transitioning to law enforcement and judicial roles. He served as a deputy sheriff and deputy clerk in Yell County, Arkansas, and later became an attorney. During the American Civil War, he held a military position as a captain. Boles transitioned to the judicial system, serving as a judge and later as a United States marshal. He held various judicial appointments and was active in the Republican Party, including a run for Governor of Arkansas.

Thomas Boles presents a fascinating blend of local advocacy and federal alignment, particularly in his support for regional industrial growth while navigating national Reconstruction policies. His military service on the Union side during the Civil War juxtaposes with his later judicial roles under President Rutherford B. Hayes, indicating a complex approach to governance. Boles's consistent engagement with the Republican Party, coupled with his surprisingly strong showing in the 1884 gubernatorial race, suggests a politician deeply rooted in his ideological convictions yet strategically adaptable to shifting political landscapes.