Henry Hoʻolulu Pitman  Timothy Henry Hoʻolulu Pitman (March 18, 1845 – February 27, 1863) was an American Union Army soldier of Native Hawaiian descent. Considered one of the "Hawaiʻi Sons of the Civil War", he was among a group of more than one hundred documented Native Hawaiian and Hawaii-born combatants who fought in the American Civil War while the Kingdom of Hawaiʻi was still an independent nation. Born and raised in Hilo, Hawaiʻi, he was the eldest son of Kinoʻoleoliliha, a Hawaiian high chiefess, and Benjamin Pitman, an American pioneer settler from Massachusetts. Through his father's business success in the whaling and sugar and coffee plantation industries and his mother's familial connections to the Hawaiian royal family, the Pitmans were quite prosperous and owned lands on the island of Hawaiʻi and in Honolulu. He and his older sister Mary were educated in the mission schools in Hilo alongside other children of mixed Hawaiian descent. After the death of his mother in 1855, his father remarried to the widow of a missionary, thus connecting the family to the American missionary community in Hawaiʻi. However, following the deaths of his first wife and later his second wife, his father decided to leave the islands and returned to Massachusetts with his family in 1861. The younger Pitman continued his education in the public schools of Roxbury, where the Pitman family lived for a period of time. Leaving school without his family's knowledge, he made the decision to fight in the Civil War in August 1862. Despite his mixed-race ancestry, Pitman avoided the racial segregation imposed on other Native Hawaiian recruits of the time and enlisted in the 22nd Regiment Massachusetts Volunteer Infantry, a white regiment. He served as a private in the Union Army fighting in the Battle of Antietam and the Maryland Campaign. In his company, Private Robert G. Carter befriended the part-Hawaiian soldier and wrote in later life of their common experience in the 22nd Massachusetts. Compiled decades afterward from old letters, Carter's account described the details surrounding his final fate in the war. On the march to Fredericksburg, Pitman was separated from his regiment and captured by Confederate guerrilla forces. He was forced to march to Richmond and incarcerated in the Confederate Libby Prison, where he contracted "lung fever" from the harsh conditions of his imprisonment and died on February 27, 1863, a few months after his release on parole in a prisoner exchange.