Following their completion, Ryan spearheaded the firm's expansion into the United States of America in the 1860s; capitalising on the country's lack of labour availability due to the American Civil War.

[7][8] In 1880, Ryan and his brother were awarded the railway development contracts for the new Pembina-St. Boniface line track —including 100 miles northwest of Winnipeg— by Sir Charles Tupper and the Manitoba provincial government.

[9] In addition to the railway development, the contracts also included the building of a covered bridge to connect the west and east portions of the Pembina-St. Boniface line across the Red River.

[10] The following list is in chronological order: In 1887, Ryan joined the mayor of Brockville, Ontario, David S. Booth[11] and Prescott-based developer James Cosgrove[12] to establish the firm Ryan, Cosgrove & Booth; which secured the contract to build the Guelph Junction Railway.

[22][21] The couple lived in Brockville following their marriage for three decades until 1894 when they moved, along with their four live-in house staff, into a red-brick mansion on the storied Jarvis Street in Toronto, Ontario.

[37][38][39] Through his sister, Ryan was the uncle of Margaret Isabelle McHenry (née Doheny), the president of the Catholic Women's League of Canada.

[23][42] Ryan's requiem mass was conducted by Catholic Archbishop Charles-Hugues Gauthier at the Our Lady of Lourdes Church and was attended by the Irish Bishop of Lancaster, Thomas Flynn.

[43] The pall-bearers included: Lieutenant Governor of Ontario, Sir John Morison Gibson; Canadian Senator, George Taylor Fulford; Ontario Member of Parliament, James Joseph Foy; M.L.A., William Henry Comstock; M.J. Hanley, Lieutenant-Colonel Edward George Mason; Canadian Senator, G.P.