[59] However, he identified with the herdsman of history, a man he said possesses "few of the emasculated, milk-and-water moralities admired by the pseudo-philanthropists; but he does possess, to a very high degree, the stern, manly qualities that are invaluable to a nation".[60][61] He reoriented and began writing about frontier life for national magazines; he also published three books: Hunting Trips of a Ranchman, Ranch Life and the Hunting-Trail, and The Wilderness Hunter.[62]
Roosevelt successfully led efforts to organize ranchers there to address the problems of overgrazing and other shared concerns, which resulted in the formation of the Little Missouri Stockmen's Association. He felt compelled to promote conservation and was able to form the Boone and Crockett Club, whose primary goal was the conservation of large game animals and their habitats.[63] In 1886, Roosevelt served as a deputy sheriff in Billings County, North Dakota. During this time he and two ranch hands hunted down three boat thieves.[64]
The uniquely severe U.S. winter of 1886–1887 wiped out his herd of cattle and those of his competitors and over half of his $80,000 investment.