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He embarked in the cattle business in 1854. For three years he made annual drives to Shreveport on Red River in Louisiana from which his cattle were shipped by steamboat to market in Mississippi River towns—Memphis, Vicksburg, Natchez, New Orleans. For better range he moved to Denton County in 1857 and then to Concho County in 1863. He remained on the Concho River until he pulled up stakes and set out for New Mexico in 1867.
It was not wholly the spirit of the innate pioneer that prompted John Chisum to move farther and farther west. The lure of markets led him on. There were no markets to the north. From the Concho straight north to the fur posts of the Hudson's Bay Company in Canada lay one wide sweep of wild country without towns or settlers, peopled by Indians, pastured only by buffalo and antelope. Beyond the eastern borders of Texas there were markets at Shreveport, Little Rock, and Baxter Springs. There were markets to the south among the Texas gulf ports. But the profits in these Eastern and Southern markets were small and the trail was long and difficult. Strangely enough, Chisum's best markets lay to the west.
In the southwestern corner of the United States, Spanish settlements had been flourishing for more than two hundred and fifty years. Oñate founded Santa Fé in 1608; the town was contemporary with Jamestown; it was a sturdy village when the Pilgrims landed at Plymouth Rock. When Chisum turned his eyes toward New Mexico, it was the metropolis of the Southwest, grown rich on the trade of the Santa Fé trail. The population of the land that had once been suzerain to His Catholic Majesty of Spain had been vastly increased by a heavy influx of American settlers. Santa Fé, Taos, Las Vegas, El Paso, Albuquerque held out promise of rich markets to the Texas