 Webster was elected to Calgary City Council as an Alderman in 1919 and served for three years.He became Mayor in 1923 defeating former mayor Michael Copps Costello and Labor candidate J. E. Worsley in the December 13, 1922 municipal election on the first ballot.Webster would be elected for a second term in the December 12, 1924 general election, and was acclaimed for a third term on December 9, 1925.