Near the forks of the Grand River in present-day Perkins County, in August 1823, while scouting ahead of his trading partners for game for the expedition's larder, Glass surprised a grizzly bear mother with her two cubs. Before he could fire his rifle, the bear charged, picked him up, and threw him to the ground. The bear threw his flesh to its cubs. Glass got up, grappled for his knife, and fought back, stabbing the animal repeatedly as the grizzly raked him time and again with her claws.
Glass managed to kill the bear with help from his trapping partners, Fitzgerald and Bridger, but was left badly mauled and unconscious. Henry (who was also with them) became convinced the man would not survive his injuries.
Henry asked for two volunteers to stay with Glass until he died, and then bury him. Bridger (then 19 years old) and Fitzgerald (then 23 years old) stepped forward, and as the rest of the party moved on, began digging his grave.[2] Later claiming that they were interrupted in the task by an attack by "Arikaree"[citation needed] Indians, the pair grabbed Glass's rifle, knife, and other equipment, and took flight. Bridger and Fitzgerald incorrectly reported to Henry that Glass had died.
Despite his injuries, Glass regained consciousness. He did so only to find himself abandoned, without weapons or equipment, suffering from a broken leg, the cuts on his back exposing bare ribs, and all his wounds festering. Glass lay mutilated and alone, more than 200 miles (320 km) from the nearest American settlement at Fort Kiowa on the Missouri.
In one of the more remarkable treks known to history, Glass set his own leg, wrapped himself in the bear hide his companions had placed over him as a shroud, and began crawling. To prevent gangrene, Glass laid his wounded back on a rotting log and let the maggots eat the dead flesh.
Deciding that following the Grand River would be too dangerous because of hostile Indians, Glass crawled overland south toward the Cheyenne River using Thunder Butte, a prominent landmark visible for miles, as a navigational tool. It would take him six weeks to reach the Cheyenne River. Glass survived mostly on wild berries and roots. On one occasion he was able to drive two wolves from a downed bison calf, and feast on the meat. Glass was aided by friendly natives who sewed a bear hide to his back to cover the exposed wounds as well as providing him with food and a couple of weapons to defend himself. He made his way to the Cheyenne River, fashioned a crude raft and floated down the river, eventually reaching the safety of Fort Kiowa.
After a long recuperation, Glass set out to track down and avenge himself against Bridger and Fitzgerald. When he found Bridger, on the Yellowstone near the mouth of the Bighorn River, Glass spared him, purportedly because of Bridger's youth. When he found Fitzgerald, he discovered that Fitzgerald had joined the United States Army, Glass purportedly restrained himself because the consequence of killing a U.S. soldier was death. However, he did recover his lost rifle.
Glass, along with four others, was dispatched by Ashley to find a new trapping route, by going up the Powder River, then across and down the Platte to the bluffs. The party set off in a bullboat. Near the junction with the Laramie River, they discovered some 38 Indian lodges, with several Indians on the shore. The Indians appeared to be friendly, and the trappers initially believed them to be Pawnees. After going ashore and dining with the Indians, Glass discovered that the Indians actually belonged to the Arikara nation, who, after several past encounters, were anything but friendly with the whites. The party quickly got in the bull boat and paddled for the far shore. The Indians promptly swam in after them and both reached the shore around the same time. Two men, Marsh and Dutton, escaped and reunited later, but the other two, More and Chapman, were quickly overtaken and killed. Glass was lucky enough to find a group of rocks to hide behind, and was not discovered by the Arikaras. Glass also found his knife and flint in his shot pouch after the ordeal. He fell in with a party of Sioux and traveled with them back to Fort Kiowa.