He was born in Kildonan, Sutherland, Scotland.[1] He taught school there for two years and came to Zorra Township in Oxford County, Upper Canada, where he taught school for several years. Oliver then moved to Woodstock, where he became a dry goods merchant. He served on the town council, becoming reeve for Woodstock and was county warden in 1866. He was elected in the North riding of Oxford in an 1866 by-election held following the death of Hope Fleming Mackenzie and served until Confederation;[2] in 1867, he was elected to the House of Commons[1] and served until his death in Woodstock in 1880.[3]