Hollow Horn Bear was born in what today is Sheridan County, Nebraska. He was the son of chief Iron Shell. Although he initially raided the Pawnee, he later was involved in harassing forts along the Bozeman Trail with other Sioux leaders between 1866 and 1868. During this period, he became famous as the chief who defeated Capt. William Fetterman. However, he began to favor peace with the whites during the 1870's. He became a celebrity in the East, and was present at several functions as a native representative. He was featured on a 14-cent postage stamp and on a five dollar bill.
He was appointed the head of Indian police at the South Dakota Rosebud Agency, and arrested Crow Dog for the murder of Spotted Tail. He was also involved in treaty negotiations. In June 1895 he demanded the removal of J. George Wright, an unpopular Indian Agent, over the reduction of Indian rations and fright allowances. Hollow Horn Bear issued 21 days' notice to the Agent to abdicate and for the Whites to leave the Reservation. In September 1895 Agent Wright imprisoned Hollow Horn Bear in the agency's guardhouse but, subsequently, released him. In 1896 Wright was promoted to the position of Indian Inspector, with authority that extended over numerous Indian Reservations and agencies. In 1905, Hollow Horn Bear was invited to take part in the presidential inauguration of Theodore Roosevelt, and in 1913, he led a group of Indians to the inauguration parade of President Woodrow Wilson. He caught pneumonia during the visit and died.*