The Clouston family of Montreal were integrally linked to the Bank of Montreal. The head of the family, Edward Seaborne Clouston (1849-1912), was its General Manager. He and his wife Annie's two daughters, Margery Meredith (b. 1882) and Osla (1879-1905) were friends of Gwendolen Marjorie Howard, and both appear, along with their parents and family friends, in numerous photographs taken at or near their family estate, Boisbriant, located in Senneville, Quebec. Formerly the home of Sir John Joseph Caldwell Abbott, Canada's third Prime Minister, the large estate included the ruins of Fort Senneville and was located in close proximity to Gwendolen Marjorie Howard's other friends, the Shepherd family (Como), the Angus family (Senneville), and the Grants (Sainte-Anne-de-Bellevue).

Of the two Clouston daughters, only Margery (often identified by her nickname, "Daw") appears in photographs taken away from the family's Senneville estate, particularly at the Porteous family home on Île d'Orléans near Quebec City. Her sister Osla was often in poor health, and either chose not to, or was discouraged from participating in taxing excursions by her parents who were concerned about her condition. She died suddenly of heart disease in Montreal on June 3, 1905; collapsing while preparing to leave for a dinner hosted by Lady Allan to celebrate a wedding at which Osla was to be a bridesmaid.

Mr Clouston, born in Moose Factory, Ontario, was the son of James Stewart Clouston, the chief factor of the Hudson's Bay Company. He began work as a clerk for the Bank of Montreal in 1865, reaching the position of General Manager in 1891, a position which he held until he left the bank in December 1911. In recognition of his success at the bank and in other business and philanthropic concerns, Clouston was made a baronet in 1908. He left the bank reportedly over frustration that he was not selected as President in 1910. The position was instead offered to his Senneville neighbour, Richard Baldword Angus. Clouston was replaced as General Manager by his Assistant General Manager, Vincent Meredith (later Sir Vincent Meredith), who eventually became the bank's president in 1913.

Upon leaving the bank, Sir Edward was able to purchase the General Manager's house on Peel Street in Montreal's lavish square mile. This house was located only metres away from both that of his former assistant, Vincent Meredith, as well Mrs Meredith's father, Andrew Allan, President of the Allan Shipping Line. Sir Edward and Lady Clouston continued to live both at their Peel Street address and at Boisbriant until Sir Edward's unexpected death in November 1912.

Sir Edward's remaining daughter, Margery, married Dr John L. Todd, a graduate of McGill in medicine and later an Associate Professor of Parasitology. Margery and her family eventually inherited the family's Senneville estate.

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