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Born in White Sulphur Springs, Greenbrier County, West Virginia, Gillespie attended the graded schools and Concord Normal School. He taught in the public schools at White Sulphur Springs, W.Virginia, in 1891 and 1892. Principal of White Sulphur Springs High School in 1891. He studied law at Central College, Danville, Indiana. He was admitted to the bar in 1892 and commenced practice in Charleston, West Virginia. He moved to Bloomington, McLean County, Illinois, in 1894 and continued the practice of law. He also engaged in agricultural pursuits. He served in the Illinois House of Representatives in 1913 and 1914.
Gillespie was elected as a Democrat to the Seventy-third Congress (March 4, 1933-January 3, 1935). He was an unsuccessful candidate for reelection in 1934 to the Seventy-fourth Congress and for election in 1936 to the Seventy-fifth Congress. He resumed the practice of law in Bloomington, Illinois, until his death there on November 26, 1954. He was interred in Park Hill Cemetery.
This article incorporates public domain material from websites or documents of the Biographical Directory of the United States Congress.