James Dill, early Indian trader and alcalde, was born about 1766 at Lancaster, Pennsylvania. He was orphaned at age two. In 1785 he moved to New Orleans, where he stayed for two years before moving upriver to Arkansas Post and pursuing a hunter's life. He lived in Arkansas Territory for eleven years; there he married Helena Gimlech or Camiliech (Americanized as Kimble) on September 14, 1791; they eventually had four daughters and one son. The Dills moved to Natchitoches, Louisiana, in 1797 and later settled on Dill Creek in northern Nacogdoches County, where Dill farmed and, according to tradition, carried on a lucrative trade with the Indians and Spanish settlers. Two of the Dill children were baptized in Arkansas, and the rest were baptized in Texas; Maria Helena Dill, born on September 8, 1804, in Nacogdoches, was one of the earliest children born to English-speaking parents in Texas. The Dill family was living in Nacogdoches by 1799, and the family home was located at what is now the corner of North and Hospital streets.
While living in Nacogdoches in 1802 Dill applied for a grant of four leagues of land west of the Angelina River and north of El Camino Real (see OLD SAN ANTONIO ROAD). Not until July 1828, however, did his widow, Helena, obtain title to the land. The Dill family left Nacogdoches and moved to Fort Jesup, near Mansfield, Louisiana, in 1813 to avoid becoming embroiled in the Gutiérrez-Magee expedition and to send their children to the newly constructed school. After Erasmo Seguín invited Dill and others back to Nacogdoches in 1820, Dill became involved in local politics and the next year was elected alcalde for the Nacogdoches ayuntamiento-the first Anglo-American to be so honored. He was unable to read or write but exerted great influence. His lack of legal knowledge caused certain opposition to his holding elected office, however, and in 1823 a junto headed by Joseph Durst, alcalde Juan Seguín (Dill's opponent in the 1823 election), José Antonio Sepúlveda, José Antonio Chirino, and Mariano Sanches ousted Dill. Juan Seguín replaced him on October 10, 1823. On May 18, 1825, Dill shot and killed Charles Duboys. Luis Procela, then alcalde of Nacogdoches, called upon other alcaldes of East Texas to sit with him in Dill's trial; a jury of twelve men found Dill not guilty, but José Antonio Saucedo, political chief in Bexar, later instructed Procela that Mexican law did not authorize jury trial. Procela was ordered to organize militia companies and rearrest Dill. In June 1825 Dill escaped to Natchitoches. On November 21, 1825, a fall from a horse led to his death.