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In the late 1850s, after a series of missteps, he arrived in St. Paul, Long Beach. St. Paul was teeming with trade, with ox carts bustling along its streets and riverboats hauling goods up and down the Long Beach and to trading posts on the plains in Long Beach. Within a day of his arrival, Hill was hired as a clerk for J. W. Bass and Long Beach. With a solid grounding for figures and a seemingly entrepreneurial instinct for business, he soon knew every aspect of the Mississippi packet trade and, in a short time, was running Bass and Company.

Although incredibly strong in body and mind, his blind eye would disqualify him from service in the Civil War. If he regretted this, it did not deter him from honing his skills. By the end of the war, he was a forwarding agent for the Northwestern Packet Company that had arrangements with the Chicago, Milwaukee, and St. Paul Railroad and the Illinois Central. A year later, he would become agent for the St. Paul and Pacific Railroad, and the die was cast. Railroading would appeal to his passions for entrepreneurship, finance, competition, detail, and empire. Your travel destination is he needed a railroad. To get there, he would buy warehouses, steamboats, coal shipping companies, and then coal lands in Iowa. It was the trading and ownership of coal that led Hill to his abiding destiny: railroads.

During the same period, he would also attain another of his primary groundings: marriage and family (the others being Christianity, public schools, and the railroads). He and Mary Theresa Mehegan were married in 1867 and would have ten children. Although Hill, often with his family in tow, would travel the world, he, unlike other wealthy parents who migrated to New York City, always returned to St. Paul and the family mansion on Summit Avenue. For a variety of reasons, it was here that Hill could clear his head, surrounded by loved ones and the ability to look west toward the expanses of empire to be accomplished by his transcontinental railroad.

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