According to , early historical records indicate that "Redskin" was used as a self-identifier by Native Americans to differentiate between the two races. Goddard found that the first use of the word "redskin" came in 1769, in negotiations between the Piankashaws and Col. John Wilkins. Throughout the 1800s, the word was as they negotiated with the French and later the Americans. The phrase gained widespread usage among whites when James Fenimore Cooper used it . In the book, Cooper has a dying Indian character lament, "There will soon be no red-skin in the country."

The Pioneers and other books by Cooper were largely seen as sympathetic toward Native Americans and their struggles in the 1800s. Decades later, the word "redskin" began to take on a negative, increasingly violent connotation. Author L. Frank Baum, best known for his classic The Wizard of Oz, celebrated the death of Sitting Bull and the massacre at Wounded Knee calling for the extermination of all remaining Native Americans. In one of the December 1890 pieces, Baum wrote, "With his fall the nobility of the Redskin is extinguished, and what few are left are a pack of whining curs who lick the hand that smites them."

At around the same time the word "redskin" was becoming a word with negative connotations, other Native American words and images were becoming increasingly popular symbols for sports teams. In , J. Gordon Hylton found that team owners frequently began using words with indigenous connections in the 1850s. "Native American names appear to have been chosen to emphasize the 'Americanness' of the team and its patriotic character," writes Hylton, without noting that at the same time popular culture was relegating Native Americans to the foreign and the extreme.