Early Career
Hill was born in the small town of Rockwood in southern Ontario, on September 16, 1838. Because his father died when Hill was young, he had to temporarily forgo formal education to help with family finances. Showing academic ability, however, he received free tuition at Rockwood Academy. Hill later lost an eye to an accidental arrow shot, preventing him from pursuing the career in medicine that his parents had hoped for.
At 18 Hill became interested in the Far East and decided on a career in trade. He headed west in hopes of joining a team of trappers, arriving by steamboat in St. Paul, a major fur-trading center, on July 21, 1856. However, Hill missed the last brigade of the year and had to stay in the city. Nonetheless, he grew to like St. Paul and decided to remain there.
Hill’s first job was as a forwarding agent for the Mississippi River Steamboat Company. He set freight and passenger rates and learned about steamboat operations. Unable to fight in the War Between the States because of his eye, Hill organized the First Minnesota Volunteers. He also worked as a warehouseman, pressing and selling hay for the troops’ horses. It was here that he learned how to buy and sell goods at a profit and use the least expensive method to ship goods.
After the war, Hill became an agent for the First Division of the St. Paul & Pacific Railroad. At the time the line used wood for fuel. Hill believed rightly that coal would be cheaper, so he made a contract with the company to supply it. He also formed a business with Chauncey W. Griggs, a Connecticut man in the wholesale grocery business. Together they created Hill, Griggs & Company, a fuel, freighting, merchandising, and warehouse company.
Hill later became interested in the Red River of the North that flows north to Lake Winnipeg. Since Fort Garry (now Winnipeg) was an important Hudson’s Bay Company trading post, Hill began transporting personal belongings there. Later, Hudson’s Bay employee Norman Kittson left the company to join Hill in forming the Red River Transportation Company.
In 1870 Hill traveled up the Red River to investigate a French and Indian mob that had captured Fort Garry. During that trip and others, Hill saw the rich soil of the region while observing the St. Paul & Pacific’s steady decline. He became convinced that he could make the line profitable by extending it to Fort Garry. When the panic of 1873 put the railroad under receivership, he saw his chance to buy it and other lines in crisis.
Hill and Kittson went to Donald Smith of the Hudson’s Bay Company and told him their plan. Smith offered money and approached George Stephen, president of the Bank of Montreal. Together, the four of them bought the St. Paul & Pacific for $280,000 ($3.9 million current), which Hill estimated as only 20 percent of its real value.
Hill purchased rails, rolling stock, and locomotives, and hired laborers who laid more than a mile of track a day. In 1879 the tracks were connected at St. Vincent, Minnesota, to a Canadian Pacific branch from Fort Garry. Since the Canadian Pacific’s transcontinental route was not yet completed, all traffic through Fort Garry had to use Hill’s route. He received two million acres of land through the Minnesota Land Grant for completing the rail line on time. He also renamed his railroad the St. Paul, Minneapolis, & Manitoba. His timing was perfect since the area experienced two exceptional harvests that brought extra business. In addition, a major increase of immigrants from Norway and Sweden allowed Hill to sell homesteads from the land grant for $2.50 to $5 an acre.