He too was a politician, serving as a member of the House of Commons of Canada and a federal cabinet minister, and briefly as the eighth premier of Manitoba.

Macdonald served with the 14th Battalion Volunteer Militia Rifles during the summer of 1866 near Cornwall, in anticipation of a Fenian invasion.

While at the University of Toronto, he enrolled in The Queen's Own Rifles of Canada on 13 October 1868 as a Rifleman and rose to the rank of Sergeant before being commissioned as an Ensign on 22 April 1870.

Macdonald then joined the expedition of Colonel Garnet Joseph Wolseley as an Ensign in the 16th Company of the 1st (Ontario) Battalion of Rifles and made the trek to the Red River settlement in Manitoba.

This occurred at a time when the Conservative Party was suffering from internal divisions, and was due to face the public in a general election.

The party had suffered severe losses to Thomas Greenway's Liberals in the elections of 1888, 1892 and 1896, and had lacked direction since the death of former Premier John Norquay in 1889.

Macdonald accepted the leadership position, and (though without seat in the legislature) spent the next two years touring the province in anticipation of the next election.

This was a progressive document by the standards of its age, calling for an independent board of education, new agricultural and technical colleges, a Workmen's Compensation Act, prohibition, and the nationalization of railways.

Macdonald narrowly defeated incumbent Liberal John D. Cameron in Winnipeg South, and was sworn in as Premier on January 10, 1900.

Macdonald resigned as Premier on October 29, 1900, and challenged Minister of the Interior Clifford Sifton in the riding of Brandon.

Sifton was the most powerful cabinet minister in western Canada, but the Conservatives believed that Hugh John's personal popularity would be enough to defeat him.

Immigrants arrested during the strike appeared before him and he ordered them sent to an internment camp at Kapuskasing from where they were eventually deported without the right to formal hearings.