Kennedy was born in Stepney, in London, England in 1861. His parents were John Kennedy, an Anglican priest and Helen Stodart Blackie. He was educated at the City of London School until 1877 when he joined a shipping firm. Four years later he journeyed to Canada with the intention of learning to farm but became a journalist instead. He became a correspondent for the Montreal Witness as well as the New York Herald. His most notable assignment was to cover the Riel Rebellion in 1885. He was present during the relief of Battleford, the Battle of Cut Knife and the pursuit of Big Bear. Afterwards he became city editor for the Witness, a position which he held for five years. In 1890 he returned to England to become editor of The Times Weekly. During his employment with The Times, he travelled back to Canada where he toured the country and wrote informational booklets for the Canadian government on the many regions.