Hosea H. League, one of the Old Three Hundred colonists, first visited Texas in company with his brother-in-law, William D. Horton. After returning to Tennessee he decided to join the Stephen F. Austin colony and returned to Texas under provisions of the colonization act of March 1825, stating in his petition for land in March 1826 that he was thirty-six years old and was bringing his wife and five slaves. In August 1826 he signed a petition for the establishment of Matagorda. In January 1827 he was in Nashville, Tennessee, and had twenty families ready to leave for Texas and a group of colonists bound for the colony of Green DeWitt. To broaden his empresario activities, he was appointed agent for the Texas Association in March 1827 and in October 1827 was recognized by Mexican authorities as the agent of the Nashville Company (later Robertson's colony).
League received title on May 25, 1827, to a sitio of land on the west bank of the Colorado River about two miles northwest of Bay City in what is now Matagorda County. He seems, however, to have made his residence in San Felipe, where he was a law partner of David G. Burnet and in a mercantile business with Seth and Ira Ingram. On February 11, 1828, he presided at the first Masonic meeting in Texas. After election as second regidor of the San Felipe ayuntamiento for 1829, he worked on a committee to formulate plans for a school and advocated taxes to build a municipal building. It wfas probably his advocacy of taxes as well as his irritable disposition that made him unpopular at San Felipe. At the end of 1829 he secured a leave of absence to go to New Orleans for his health, but he was back in San Felipe as first regidor in March 1830. In July 1830 he secured permission to operate a ferry on his grant on the lower Colorado River.
On September 2, 1830, League was implicated as an accessory when Seth Ingram shot John G. Holtham. He and Ingram were arrested and held for trial. After sixteen months in chains they were released on bond but were again arrested and were not released until the summer of 1833. During his long legal difficulties League decided to sell enough property to settle the claims against him. With his business ruined, his health gone, and his savings destroyed, he turned the work of the Nashville Company over to Sterling C. Robertson.
On November 28, 1835, the General Council appointed League first judge for the Harrisburg jurisdiction, and he presided as election judge for the choice of delegates to the Convention of 1836. After Harrisburg was destroyed, he wrote to Burnet from San Jacinto on May 21, 1836, asking to transfer the work of his office to Lynchburg. The office of Harrisburg judge was abolished on May 27, 1836. League apparently died by May 8, 1837, when James S. Holman requested that claims against and payments to the H. H. League estate be made to him.