Looking Glass was the war chief who, along with Chief Joseph, directed the 1877 Nez Percé retreat from eastern Oregon into Montana and on toward the Canadian border. The son of a prominent Nez Percé chief, Looking Glass was born around 1832 in what is now western Montana. Although he bitterly resented white encroachments on his ancestral lands, he opposed going to war with the United States over its plans to force his people onto the small reservation assigned to them at Lapwai, Idaho.

When the Nez Percé and the U.S. Army first clashed at Whitebird Canyon on June 17, 1877, Looking Glass was already living on the Lapwai reservation, as he had agreed to do. Nevertheless, GeneralOliver Howard believed that Looking Glass would soon join the fighting, and he sent a detachment of troops to arrest him. Howard's plans backfired, however, for Looking Glass eluded arrest and fled the reservation to join Joseph and his fugitive band just as Howard had feared.

For both better and worse, the Nez Percé flight bore the mark of Looking Glass's leadership. A respected battlefield commander, he convinced the band to flee to Montana, despite Joseph's opposition, and then persuaded them to stop at Big Hole, where he incorrectly believed they would be free from attack. After soldiers under the command of Colonel John Gibbon surprised the Nez Percé there on August 9, inflicting heavy casualties, Looking Glass lost much of his prestige as a military leader.

Nearly two months later, when the Nez Percé were finally surrounded by Colonel Nelson A. Miles's troops in Northern Montana's Bearpaw mountains, Looking Glass remained stubbornly opposed to surrender. By this time, however, Chief Joseph had concluded that surrender was the only viable option, and on October 5, he rode out to hand over his rifle. That same day, Looking Glass set out to join Sitting Bull's band in Canada, but before he could make it to the border, he was killed by a Cheyenne scout.