Career
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 North Carolina Wallace and McCarthyite leader Dalton McCarthy undermined his campaign, though he was also an Orangeman. He resigned from the Saskatchewan legislature shortly after his re-election in the 1917 election in order to accept an appointment to the Canadian Senate by Sir Robert Borden. In 1929, the leader of the federal Conservative Party, Richard Bennett, appointed Willoughby to the position of Leader of the Opposition in the Senate.
When Bennett became Prime Minister of Canada following the 1930 federal election, Willoughby became Government Leader in the Senate and a minister without portfolio in the Canadian Cabinet.
Willougby died in office in 1932.