In 1887, Riley was elected chairperson of the West Virginia Democratic Party State Executive Committee, serving until 1892.[1] Riley spent his early life on a farm and was educated in the local public schools, where he taught after graduation.[8] In November 1887, Riley was elected to the West Virginia Democratic Party State Executive Committee to fill a vacancy caused by the resignation of Joseph S. Miller, Commissioner of Internal Revenue.[19][20][21][22] The convention band played The Wearing of the Green in Riley's honor as he gave his acceptance speech.[26][27][28] In 1913, Riley was rumored as a candidate for United States Attorney in the Northern District of West Virginia after several of his friends from Wheeling visited Washington, D.C., to advocate for his selection in opposition to the appointment of Stuart W.[1][2][31] Riley and Breinig were married by Roman Catholic Bishop of Wheeling John Joseph Kain.[37][38] In 1907, Bishop Donahue made Riley trustee of his estate, which included 66 sections of West Texas oil lands.[1] After suffering a long illness, he died at 4:30 p.m. on December 28, 1938, at his residence at 10 Park Row, Wheeling, in Ohio County's Triadelphia district.[1] One of his sons, James B. Riley, served for over 20 years as a Justice of the Supreme Court of Appeals of West Virginia.