Six distinctive livestock brands on the Trail Boss monument are tied to historical figures who were instrumental in developing southeastern New Mexico. The RB brand belonged to Hugh Beckwith and his sons Robert and John, whose family moved into southern New Mexico in the late 1870s and ranched near Lakewood between Artesia and Carlsbad, while the 69 brand was used by John Jones, eldest son of William H. Jones, who ranched on Rocky Arroyo. The Beckwith and Jones families were small ranchers within the boundaries of the larger John Chisum ranch near Roswell, and Robert Beckwith and John Jones took part in driving the Billy the Kid gang from the McSween home in Lincoln in 1878 during the Lincoln County War, where Beckwith was killed; a few years later John Jones killed John Beckwith in a duel over calf ownership, then Beckwith family friend Bob Olinger killed Jones in revenge, and Olinger was later killed by Billy the Kid, a friend of John Jones. Hugh Beckwith used the RB brand until his murder at his store on the Texas-Mexico border in 1890, and after John Jones's death his brother Bill re-registered the 69 brand in Roswell in 1881 and used it until his death in 1952. After the Civil War, Texas cattlemen Charles Goodnight and Rueben Segrest rounded up wild cattle in North and Central Texas and drove them to military markets in New Mexico and beyond; Goodnight also collected cattle from small ranches for delivery to market and used the O brand on the center of the body to mark cattle that traveled with his herd but were not his own stock, making the brand common along the Goodnight Loving Trail through New Mexico. After his trail drive era, Goodnight established ranches in Texas and Colorado. Segrest established the S Cross in the area between Lakewood, Dayton, and the northern half of the Guadalupe Mountains, where he began branding wild cattle; about 1900 he hired Tom Runyan, who later became his partner, and after Segrest's death in 1916 Runyan assumed ownership of his partner's land and cattle. In 1878 Walter E. Thayer, son of a wealthy Maryland businessman, worked as a cowboy for John Chisum and over the next 20 years accumulated orchards, farmland, rangeland, cattle, and money; around 1900 he bought most of the permanent water sources on the south end of the Guadalupe Mountains, which allowed him to establish orchards and agricultural fields and graze hundreds of cattle under the X Bar brand, also the name of his ranch. Charles B. Eddy also began as a cattleman before turning to farming, used the VVN brand on his ranch headquartered north of Carlsbad at La Huerta, and joined Pat Garrett and others in establishing irrigation projects from Roswell to Carlsbad.