One of the founding members of the Canadian Pacific Railway is given a colourful introduction in Pierre Berton's classic popular history
The Last Spike (1971). Berton notes that Hill was, "a tougher and rougher specimen than his colleagues. With his single, burning eye, his short, lion's beard and long mane, he looked like a bit of a pirate, which, in truth, he was." As a child of nine Hill had lost his eye in an accident. In his youth he had to work as a clerk in an Upper Canadian grocery store to help his impoverished family. In 1856 Hill would begin to build his railway empire from scratch. He moved to the booming city of St. Paul, and soon began his own shipping company. This meagre start was the base for numerous railway interests. In 1874, he teamed together with Donald Smith, Norman Kittson, and George Stephen to complete the St. Paul and Pacific railway to the Canadian border. This partnership would lead to his eventual position on the board of the Canadian Pacific Railway.
Berton attributes the decision-making of Hill, who had been convinced by naturalist John Macoun that the southern prairies were inhabitable, as instrumental in selecting the southern route through Calgary and the yet to be explored Kicking Horse Pass, instead of along the old settlements on the North Saskatchewan River. The original route, surveyed by Sandford Fleming, bore northwest from Selkirk, Manitoba (near Winnipeg), and continued through Battleford and the Yellowhead pass. Due to the selection of the southerly route, the nascent communities of Brandon, Regina, Moose Jaw and Calgary were all to flourish into metropolitan centres on the northern Great Plains.
The southern route was also more ideally located to curb competition from the closest American railway, the Northern Pacific, and any other Canadian railways that may have emerged when the CPR monopoly clause, which prohibited railways building within 15 miles of the international border, ran out.
A central tenant of Hill's railway philosophy was that the first railway through the frontier would generate its own business. As Hill claimed, "if we build this road across the prairie, we will carry every pound of supplies that the settlers want and we will carry every pound of produce that the settlers wish to sell, so that we will have freight both ways."
Hill would leave the CPR in 1883, due to the mismanagement of the Manitoba line, which Hill felt was neglected due to the larger projects of the CPR. In 1889 the Manitoba line would become the Great Northern railway, and grow to dominate the northern American plains to the Pacific. Hill is regarded as one of the greatest empire builders of nineteenth century North American business.
Canadian Encyclopedia Article on Hill
