Roebuck ran a Liberal candidate in Temiskaming in the 1911 Ontario general election| and the 1914 Ontario general election| but failed to get elected. He also ran in the 1917 federal election. He was involved with the United Farmers of Ontario and its successor, the Progressive Party, in the 1920s before rejoining the Liberals. He finally won a seat in the Legislative Assembly of Ontario in the 1934 provincial election that brought the Ontario Liberal Party led by Mitchell Hepburn to power.