Running Antelope - head chief of the Hunkpapa tribe of the Lokata Indians in the mid-19th century. He is the only Native American to be depicted on US Paper money.
The 1899 $5 silver dollar paper money certificate was printed up until the early 1920's and is in abundant supply - tens of millions were printed. But high quality versions can be cost investors over $1,000-$5,000+
But the government messed up the new $5 Note:
"the government thought would be a far less controversial symbol — a Sioux Indian chief. However, workers at the Bureau of Engraving and Printing substituted the headdress of a rival tribe, the Pawnee, on the final image. This switch precipitated not only a political scandal but caused additional ill will between the Sioux and Pawnee peoples."