What is wrong with the 5 dollar silver certificate of 1899?

Answer 1

The Native American shown on the bill is Running Antelope, a famous leader, warrior, orator, and eventually a diplomat. The bill is very controversial because the designer took it upon himself to depict Running Antelope wearing a Pawnee headdress, claiming that it fit better on the bill than the correct portrait with a Sioux headdress.

Running Antelope was an important tribal chief within the Sioux Nation, and his portrait is one of the few on American currency that depict a historical figure rather than a composite (e.g. the Indian Head nickel), an allegorical figure (Indian Princess gold pieces), or a stylized interpretation (Sacajawea dollars).