Initially, he spent two years as a journalist before enrolling in the University of Manitoba's law school.
During World War I, Kennedy demonstrated his dedication to service by joining the Canadian Expeditionary Force in November 1915.
He served in France with the 46th Battalion from May 1917, earning recognition for his bravery at the Battle of Passchendaele, where he was wounded and received the Military Cross.
Further commendations followed for his contributions to the Battle of Valenciennes, leading to field promotions to captain and then major before his discharge in 1919.
Notably, Kennedy assumed the role of Chairman of the Royal Commission on Price Spreads and Mass Buying during Prime Minister R.B.