The Five Dollar Silver Certificate of 1899 shows the head portrait of "Ta-to-ka-in-yan-ka ", also known as Chief Onepapa (Running Antelope), a member of the Hunkpapa Sioux (a part of the Dakota Tribe - which means 'allies'). Of all the Plains tribes, the Sioux were the most resolute in resisting white men's incursions upon their land.

This is the only issue of US paper money where an Indian was selected as the central motif. The portrait was engraved by George F. C. Smillie, using the feathered war bonnet of the Pawnee tribe (so as to make it fit in the allowed space).