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Morgan Stanley MS-N has a new head of its Canadian investment bank for the first time in 19 years, with president Dougal Macdonald retiring this month and mining specialist Richard Tory taking the top job.

Mr. Macdonald and his colleagues at the New York-based investment dealer have been central players in domestic deals for the past two decades. At the beginning of January, Mr. Tory took the helm of a firm that consistently ranks among the top five financial advisers on Canadian mergers and acquisitions.

“The wonderful thing about Morgan Stanley is they treat the business as a team sport. I feel fortunate to have played on an incredible team,” Mr. Macdonald said in a recent interview. The former lawyer plans to take a vacation this winter, then look for opportunities on corporate and charitable boards and public-policy roles.

Mr. Macdonald joined Morgan Stanley in 1999 after a successful first career as a corporate partner at Osler, Hoskin & Harcourt LLP. In 2004, the investment bank named him president and managing director in Canada. The firm is one of the few global dealers with offices across the country, including Toronto, Vancouver, Calgary and Montreal.

Mr. Macdonald covered a variety of sectors, with a focus on financial institutions and the country’s largest pension plans.

The long list of deals he advised on includes Bank of Montreal’s BMO-T acquisition of Bank of the West last year, Shopify Inc.’s SHOP-T initial public offering in 2015, Manulife Financial Corp.’s MFC-T acquisition of Standard Life’s Canadian operations in 2014 and the Ontario Teacher’s Pension Plan’s sale of Maple Leaf Sports & Entertainment Ltd. in 2012.

“During his time at the firm, Dougal has been instrumental in growing and strengthening the firm’s Canadian franchise,” said Eli Gross and Simon Smith, Morgan Stanley global co-heads of investment banking, in an internal e-mail. “He has served as a trusted advisor to some of the firm’s key clients in the region and led many transformational transactions.”

The new president, Mr. Tory, is also a former lawyer who joined the investment bank’s London office in 2011 and moved to Toronto in 2016. He currently runs the bank’s global mining team from Toronto.

Mr. Tory’s family is well-known in the city, as his father and uncle co-founded the law firm that still sports their surnames and one cousin – John – served as mayor of Toronto.

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