Berry describes Ashley as being a cautious and an ambitious man. He was in his mid forties at this time, and becoming known as a great adventurer would probably be considered ludicrous by Ashley. He picked good men to do the job, but when those he had hired were unable to do the job or when, as Henry did, retired from the business, he went into the field and personally led the expeditions. As a result of these explorations, he made his place in history and helped open the lands west of the Rockies to the new country of the United States.

In 1822, the new company of Ashley and Henry attempted to send three keelboats up the Missouri River. Henry led the first of the three all the way to the mouth of the Yellowstone and built a post that later became known as Fort Henry. This expedition consisted of 150 men, 60 horses and one keelboat. The second keelboat met disaster and sunk with all the provisions onboard for a loss of $10,000. Ashley then made the decision to lead the expedition with the third boat to meet Henry.

After reaching the Yellowstone and delivering his supplies and men, Ashley immediately returned to St. Louis to start building the supply expedition for the men now stationed at Fort Henry. Jedediah Smith and a small group of men accompanied Ashley downriver.