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For some time a number of Little Missouri ranchers had recognized a need for a stockmen's organization to enforce range rules. Early in 1884, Howard Eaton and several others had initiated such a movement. The Bad Lands Cow Boy supported their efforts and editorialized:
In February the stockmen had held a meeting in Little Missouri and appointed a committee to draw up bylaws for a formal organization. However, in the next meeting, the ranchers decided to defer the matter. But Roosevelt lent his support to the movement and took the initiative in bringing together the scattered stockmen along the Little Missouri for that purpose. He visited the ranchers along the river and convinced them of the desirability of organizing. Roosevelt issued calls in the Cow Boy for a meeting of the stockmen in Medora on December 19, 1884. The proceedings of this meeting reflect Roosevelt's leadership. Representatives of the 11 cattle companies attending elected him chairman of the organization, which called itself the Little Missouri Stockmen's Association, and they drew up resolutions and rules for a permanent organization. Roosevelt was authorized to draw up the constitution and bylaws. The following week the Cow Boy commented:
Roosevelt was reelected chairman in 1885 and president of the association in 1886. The Cow Boy again complimented him for his work as chairman:
Roosevelt was also an active member in the Montana Stockgrowers Association, with which the Little Missouri group was affiliated. He was admitted to membership in the Montana Stockgrowers Association in April 1885 on the recommendation of De Mores; but he did not attend its annual meeting that year. In 1886 the Little Missouri association sent Roosevelt as a delegate to one of the Montana meetings. He was placed on a committee of 16 prominent stockmen of the 2 territories to investigate the feasibility of establishing stockyards and a market in St. Paul. In another act of recognition he and Henry S. Boice were named captains of the Little Missouri Roundup. Roosevelt was also selected as one of the three members of the executive committee from the Dakota Territory. Roosevelt's role in the 1887 annual meeting was even more conspicuous. Again he was named to the executive committee. To discourage horse stealing, he introduced a resolution to require the members of the association to keep a record of all suspicious persons visiting their ranches and the brand of such person's horses. He also preferred charges before the Board of Commissioners against livestock inspector Fred Willard and succeeded in getting him discharged. This was the last meeting of the Montana Stockgrowers Association which Roosevelt attended.
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