Theodore Roosevelt Ranches the Badlands

Roosevelt built a second ranch, which he named Elk Horn, thirty-five miles (56 km) north of the boomtown of Medora, North Dakota.

On the banks of the Little Missouri, Roosevelt learned to ride western style, rope, and hunt. He rebuilt his life and began writing about frontier life for Eastern magazines. As a deputy sheriff, Roosevelt hunted down three outlaws who stole his river boat and were escaping north with it up the Little Missouri. Capturing them, he decided against hanging them (apparently yielding to established law procedures in place of vigilante justice), and sending his foreman back by boat, he took the thieves back overland for trial in Dickinson, guarding them forty hours without sleep and reading Tolstoy to keep himself awake. When he ran out of his own books, he read a dime store western that one of the thieves was carrying." While working on a tough project aimed at hunting down a group of relentless horse thieves, Roosevelt came across the famous Deadwood Sheriff, Seth Bullock. The two would remain friends for life.

After the uniquely severe U.S. winter of 1886-1887 wiped out his herd of cattle and his $60,000 investment (together with those of his competitors), he returned to the East, where in 1885 he had built Sagamore Hill in Oyster Bay, New York. It would be his home and estate until his death. Roosevelt ran as the Republican candidate for mayor of New York City in 1886 as "The Cowboy of the Dakotas"; he came in third.