Henry Bowdoin Prentiss, businessman, son of John and Ann (Kendall) Prentice, was born in Massachusetts on April 3, 1792. With his brothers Thomas G., John M., and James Prentiss he founded a land-speculation company in Hindostan, Indiana, in 1814. The company ceased to exist after John and Thomas died in November 1820. With James, Henry Prentiss then established the Union Land Company in New York in December 1830. He became its principal agent and sailed to Texas on board the schooner Crescent in January 1831. In Anahuac he established a mercantile business under the management of George M. Patrick, who was an agent for the company and who ran the store on his own during Prentiss's absence from September 1831 to March 1833. On September 21, 1831, Prentiss sailed back to New York. On March 7, 1832, he married Elizabeth Drury of Pittsford, Vermont. They had one daughter. On March 29, 1833, Prentiss again set foot on Texas soil. He wrote his brother an account of the company's affairs in Texas. As the financial future of the Union Land Company did not look too promising, Prentiss petitioned Stephen F. Austin for a headright in his own name. From San Felipe de Austin, where he had met with Austin, he traveled to San Antonio and probably Saltillo. On August 17, 1833, he was back in Nacogdoches, and on November 11 he received a title to eleven leagues of land in what is now Polk County. Prentiss then went back to New York, where he and his brother established the Trinity Land Company in January 1834. In May Henry sold his interest in the Union Land Company to James. In June 1834, having become the principal agent of the Trinity Land Company, he again sailed to Texas with his wife, other agents of the company including Gilbert L. Thompson, and a group of settlers, on board the schooner Climax. Prentiss's health began to decline, and as he could not serve in the Texas army against Mexico, he donated $200 for arms and equipment. He died in Anahuac on October 5, 1836.