At the dawn of the nineteenth century, the Osage nation found itself embroiled in heavy trading and combat with Europe and neighboring tribes. While intricate negotiations usually smoothed over problematic agreements made between these parties and the Osages, they were of no avail against American expansionism. By the 1800s, the Osages descended from a significant Midwestern-Amerindian power into a struggle for survival as a nation, foreign in their homeland. The Nineteenth-Century economic survival of the Osage people is examined during three key periods: the Thomas Jefferson presidency; the 1830s-1840s removal of eastern Indians to Osage territory; and the Osage’s implementation of the grass-leasing business to support themselves once federal aid failed to reach them. With each experience, the Osage nation recognized that the means to survival was to model certain functions of their economic and political systems after those of America’s capitalistic society. This research offers contemporary Osages a look into their past and the trials they overcame. The tribe’s tale sharply counters the common stereotype that Indians were unable to endure American expansionism financially. A comprehensive study into the Osage’s nineteenth-century economic saga has never been constructed, though this era was the most pivotal to their survival. At the beginning of Osage-American contact, it took only one generation before the tribe went from the richest, most powerful Amerindian nation in the Plains to having an 1830’s diet consisting of only bitter acorns. It was the Osage’s ascent to greatness once more that astonished not only their neighbors, but those of the modern day as well. After all, by the year 1900, the U.S. government deemed them the single richest society in the entire country.