Simpson, the governor of Kittson's old rival, the Hudson's Bay Company, described him in the 1850s as "the most extensive and respectable of the American traders doing business at Red River". In 1858 Kittson was instrumental in establishing a steamboat service on the Red River of the North, a route which was also used by the HBC. Simpson's successor, Alexander Grant Dallas, managed to convert Kittson "from an opponent into an ally". In 1862, the Hudson's Bay Company appointed him shipping agent and head of navigation on the Red River, a position he retained throughout the 1860s to the great mutual benefit of both Kittson and the HBC. He co-ordinated the import of trade goods from Britain and the export of furs by cart brigades between St. Paul and Georgetown, and by the steamship International between Georgetown and the Red River Settlement. The creation of the province of Manitoba from the former Rupert's Land in 1870 marked the end of the HBC trade monopoly. In 1872 Kittson joined up with another former competitor, James Jerome Hill, forming the Red River Transportation Company. The line had five steamboats, and Kittson had invested $75,000 by 1873. They were the only operators on the Red River during the 1870s, and were important factors in the development of Winnipeg and south Manitoba through the transportation of immigrants, mail and supplies. Railway entrepreneur In 1879, though in poor health, Kittson embarked on his last major venture. With James Hill, Kittson joined forces with Hudson's Bay Company representative Donald Alexander Smith and Montreal banker George Stephen to purchase the struggling Saint Paul and Pacific Railroad, reorganizing it into the St. Paul, Minneapolis and Manitoba Railway. It established the first rail link between St. Boniface and St. Paul. In 1880, its net worth was $728,000; in 1885 it was $25,000,000. When Kittson sold his shares in the company in 1881, it made him a very wealthy man, running his investments into the millions. These same men later formed the nucleus of a syndicate established in 1880 that built the Canadian Pacific Railway and Great Northern Railroad. Thoroughbred racing Norman Kittson was possessed of "a sartorial elegance and a love of race horses," and it was this latter interest on which he concentrated after retiring from business. His stables at Midway Park, St. Paul and at Erdenheim Farm near Philadelphia, kept some of the finest thoroughbreds and made