After the Civil War basic staples like beef were highly sought after in the Eastern United States. However, during the war Texas had accumulated a large surplus of cattle due to the fact that the Union Army blocked Texan outlets to eastern markets. Ranchers immediately saw the demand for cattle and began to drive their herds north to the railroads and the markets of the East. The existing rail lines were too small to handle the flood of Texas cattle being driven north, so in the 1860s and 1870s the Kansas towns of Abilene and Dodge City were set up as well-equipped shipping centers and became the destination for large cattle drives. These main routes took cattle drives through Indian Territory. By the 1870s some 600,000 heads of cattle a year were driven along these trails. But the time of the large cattle dive was short-lived, by 1890 cattle drives from Texas were largely over, droughts made the journey more costly and the expansion of the railroads made the long drives to railheads unnecessary.
Prettyman’s arrival in Indian Territory in 1883 allowed him to witness some of the last major cattle drives. However, by this time it was more common that American Indians and Whites established their own ranches in Indian Territory. Prettyman experienced this first-hand when he visited the large region known as the “Cherokee Outlet.” This land was leased to white ranchers from Kansas by the Cherokees beginning in 1883. On Prettymen’s first trip he stayed for an extended period at a ranch just across the Kansas border. Prettyman worked along-side the cowboys and learned much about the land and people in Indian Territory. With his camera, he was able to capture images of this increasingly rare way of life.