Career
MacGregor was a contractor and horticulturalist by profession. He was first elected to the Canadian House of Commons in the 1926 federal election and sat continuously in the chamber for thirty-six years until his defeat in the 1962 federal election when he was 79 years old. His initial experience in politics began in 1912 when he was appointed a school trustee for York Township.
Eventually he became reeve of East New York
In 1922, R.H. McGregor Elementary School was erected and named in his honour. Despite his long tenure in the House of Commons he spoke rarely and was nicknamed "Silent Bob" McGregor.
His only recorded Parliamentary speech occurred when being feted in the House on his 74th birthday. On that occasion he remarked "If a good many honorary
Members made fewer speeches in the House, they would be here longer.".