Cattle herds traveled along the Chisholm Trail from southern Texas, through Fort Worth, across Indian Territory (now Oklahoma), through Wichita, Abeline, and Dodge Kansas. Herds that were not loaded onto the railroad there were driven farther north and west through Ogallala, Sidney, and Bridgeport, Nebraska. Kendrick mentions trailing herds from there up into the Black Hills or northern Wyoming.

John B. Kendrick was a cattleman and politician in Wyoming. Born in 1857 in Texas and orphaned early in life, he grew up in poverty. In 1879, at the age of 22, he joined a cattle drive departing from Matagorda Bay on the Gulf of Mexico for Wyoming along the Chisholm Trail. He rode the trail again in 1884. In Wyoming, Kendrick was hired as ranch foreman for the Converse Cattle Company. He began purchasing cattle and soon owned a controlling stake in the company. While growing his cattle empire in Northern Wyoming and Southern Montana, Kendrick became involved in politics in the Democratic Party, serving as State Senator from Sheridan County 1911-1913, Governor 1915-1917, and US Senator 1917-1933.