Henry Perry, filibuster, was probably a native of Connecticut and possibly related to the noted military leader Daniel Perry. He joined the Gutiérrez-Magee expedition at Natchitoches in 1812, but it is unclear if he resigned from the United States Army with Magee or was an associate of Samuel Kemper. He was made a captain under Major Kemper. He was promoted to major at Bexar on June 16, 1813, succeeding Reuben Ross as commander of the Anglos. He led them against Ignacio Elizondo the next day and defeated the Spanish forces at Alazán Creek on June 20. During the struggle for command of the expedition between Gutiérrez and José Álvarez de Toledo y Dubois, Perry supported the latter, who took command on August 4. After the defeat of the insurgent army at the battle of Medina on August 18, 1813, Perry fled to Natchitoches. He rejoined the United States Army in Louisiana and served at least from December 15, 1814, to June 15, 1815, probably in the quartermaster corps.
In July 1815 he joined a scheme under Juan Pablo Anaya in New Orleans to capture La Bahía and Bexar before joining fellow insurgents near Mexico City. The call for volunteers was so public that on September 1, 1815, President James Madison had to issue a proclamation against filibustering. Perry assembled 300 volunteers at Belle Isle, near the mouth of the Atchafalaya River, but remained without funds to sail to Copano Bay. He secured a small vessel in November to ferry his troops to Galveston Bay, where they set up camp on what is now called Bolivar Peninsula. On a second voyage, the schooner foundered at the entrance to Galveston Bay and sixty men drowned. Perry ordered his men inland to a wooded eminence (known as Perry's Point through 1830) overlooking the mouth of the Trinity River below the site of modern Anahuac.
About March 1816 Perry abandoned the point and joined Luis Michel Aury on Galveston Island. Perry commanded the Anglo-Americans until the arrival of Francisco Xavier Mina in November 1816; he and his men then served under Col. Guilford Dudley Young, a veteran of the War of 1812. Perry left with the Mina expedition for Soto la Marina, Tamaulipas, on April 7, 1817. After Mina captured Soto la Marina, Perry became convinced that Mina would ultimately fail and was disturbed that Texas had not been cleared of royalists. Guided by Manuel Costillo of Camargo, he led forty-three men overland for Texas. On June 18, 1817, they reached La Bahía, where Perry demanded that Juan Ignacio Pérez surrender the garrison. When the royalists refused and prepared to attack, Perry and his men fled northeastward. On June 19 the royalist army surrounded them in a nearby wood, where most were killed or wounded. Perry was wounded but refused to surrender, preferring death by his own hand.