He ran for a seat in the Dominion House of Commons for the Conservative Party in the 1895 election, but an unofficial Tory, William Stubbs backed by the Orange Order such as its Grand Master N.C. Wallace and McCarthyite leader Dalton McCarthy undermined his campaign, though he was also an Orangeman.
Willoughby served as leader of the Saskatchewan Conservative Party and leader of the opposition from 1912 to 1917 and was Member of the Legislative Assembly of Saskatchewan (MLA) for the city of Moose Jaw.
He resigned from the Saskatchewan legislature shortly after his re-election in the 1917 election in order to accept an appointment to the Senate of Canada by Sir Robert Borden.
[2][3] He had 7 siblings; William, who was 4 years older, Lydia, Samuel, Caroline, Wesley, John, and Margaret, who were all younger.
[4][5][6] In October 1892, Wellington married Susan Thomas Jones of Germantown, Philadelphia.