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JamesDunn became involved in the legal aspects for underwriting activities for companies being listed on the Montreal Stock Exchange and in 1902 he established the J.H. Dunn and Co. stock brokerage company.
In 1944, Dunn was invited to serve on the board of directors of Canada Steamship Lines (CSL), whose ore carriers were an important transporter of ore and coal for the Algoma Steel plant which operated under a geographical disadvantage to its more southerly competitors.
As a result of the very substantial taxes on the estate left by Sir JamesDunn and Nova Scotia's Izaak Walton Killam who had died the year before in 1955, the government of Canada was able to create and provide an endowment for the Canada Council for the Arts.