His career consisted of being a farmer and thoroughbred dealer in Toronto Township[?]. He was President of the Dominion Live Stock Association[?] in 1887, 1st Vice President of the Dominion Live Stock Insurance Company[?] from 1887-1888. He also served as President of the Canadian Swine Breeders Association[?] from 1890-1891. He served as a Councillor, Deputy Reeve and Reeve before entering Federal politics.
He was chosen as Liberal Candidate in Peel County[?] to contest the general election for the House of Commons in 1891 against the sitting Conservative member W. A. McCulla[?]. Featherstone won that election with a 54 majority, in what has been described as a "keen and exciting contest". That election was declared void; a by-election which was held on February 11, 1892 gave Featherstone a majority of 133.
The next election Featherstone was against A. F. Campbell[?], publisher of The Brampton Conservator[?]. This election Featherstone triumphed by a majority of 466, or 1891 to 1425. This marked the first time any Peel candidate won by a margin of over 100. Featherstone's streak ended in 1900, to Richard Blain[?].
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