Gregg was born in Centerville, Texas on January 31, 1855. As a child, he went to public school. He graduated from King College, Bristol, Tennessee, in 1874 and studied law at the University of Virginia at Charlottesville; he was admitted to the Texas bar in 1878 and commenced practice in Palestine, Texas.
Gregg served in the Texas Senate between 1886-1888. he ran for Texas's 7th congressional district, and held a seat there between 1903-1919. He served as Chairman of the Committee on War Claims (1916-1918). He did not run for re-election in 1918 and died a month after his term ended in Palestine, Texas, and is buried in East Hill Cemetery.