Yellowtail's first official position, in 1912, was as a district representative on a tribal business committee where he negotiated grazing leases and gave the tribe a voice during land disputes.

[2] Initially, Yellowtail was in this committee to fight disputes related to Crow land, but caught the attention of other political leaders like Plenty Coups.

He attended the National Indian Memorial in New York City as an interpreter for Medicine Crow, Plenty Coups and other leaders.

[5] During this time, Yellowtail was able to get white ranchers to return 40,000 acres of land to the tribe, built a Crow Hospital, brought horses and cattle from Canada, and buffalo from Yellowstone National Park.

Yellowtail was unable to prevent the dam's construction, which began in 1961, but won a modest increase in compensation to the tribe after a divisive fight.

[5] Yellowtail continued to fight for compensation for the Crow people in the 1980s, arguing against sales of coal from reservation mineral rights controlled by the Bureau of Indian Affairs.