The family farm had failed and Ross left school in order to earn money .

[1] In his new city, Ross helped find the funds to found Branksome Hall, a new private school for girls, operated by his cousin.

[1] A supporter of and fundraiser for the Liberal Party of Canada, Ross was appointed as Lieutenant Governor of Ontario by Governor General Freeman Freeman-Thomas, 1st Marquess of Willingdon, on the advice of William Lyon Mackenzie King, in 1926.

He asked to be relieved from office in 1931 due to the onset of the Great Depression as his income from private investments declined and he was no longer sufficient to supplement the $10,000 annual salary he received in his vice-regal role.

In 1937, Ross became co-owner of the Toronto Maple Leafs baseball team.