He left high school in the middle of grade 13 to join The Royal Canadian Regiment, serving with them during World War II in England, Sicily and Italy, and rising to the rank of captain.
[2] Disagreeing with the Liberal Party of Canada's position on conscription, he joined the Progressive Conservatives after the war and served as a backroom strategist for Harry Oliver White in Middlesex East in the 1949 Canadian federal election.
When Robarts entered politics as the Progressive Conservative candidate in London in the 1951 Ontario general election, Jackson volunteered to be one of his campaign workers.
Jackson chose not to run for re-election in the 1959 Ontario general election in order to concentrate on his insurance business and family, but co-managed Robarts's own re-election campaign in London North.
[1] Robarts charged Jackson with the assignment of re-organizing the provincial party[5] and was the party's campaign chairman in the 1963 Ontario general election and 1967 Ontario general election,[2][6][7] both of which the Conservatives won with large majorities.