Timothy Henry Hoʻolulu Pitman (March 18, 1845 – February 27, 1863) was an American Union Army soldier of Native Hawaiian descent.

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.

[15][16] On his father's side, he was a great-grandson of Joshua Pitman (1755–1822), an English-American carpenter on the ship Franklin under Captain Allen Hallett during the American Revolutionary War.

[25] During Henry's early childhood, the family lived in the mansion that Benjamin Pitman had built in 1840, in an area known as Niopola, one of the favored resort spots of ancient Hawaiian royalty.

[32][note 4] In the 1850s the family moved to the capital of Honolulu where Benjamin Pitman took up banking and built a beautiful two-story house that he named Waialeale ("rippling water") at the corner of Alakea and Beretania Streets.

Mrs. Wetmore taught the children reading, writing, spelling, arithmetic and singing, while also reinforcing the curriculum with a strong adherence to the principles of the Protestant faith.

[34][35] After the death of his mother Kinoʻole in 1855, Pitman's father remarried to Maria Louisa Walsworth Kinney, the widow of American missionary Rev.

[23][38] The Pitman family returned to Massachusetts in 1861 after his father remarried to his third wife Martha Ball Paddock, giving his four children another stepmother.

[42][43] He may have proceeded the rest of the family in leaving Hawaii because the 1860 United States census registered Pitman under his teacher Solomon Adams as residing and being educated in Newton, also in the Boston area.

[41] His enlistment card during the war noted he had a dark complexion, hazel colored eyes, black hair and stood five feet eight inches.

[45] Robert G. Carter gave a brief description of his appearance in wartime letters first published in 1897:[note 5] [A] tall, slim boy, straight as an arrow.

His skin was a clear, dark olive, bordering on the swarthy, and this, with his high cheek bones, would have led us to suppose that his nationality was different from our own, had we not known that his name was plain Henry P. There was an air of good breeding and refinement about him, that, with his small hands and feet, would have set us to thinking, had it not been that in our youth and intensely enthusiastic natures, we gave no thought to our comrades' personal appearance.

[50] Many Hawaiians sympathized with the Union because of Hawaiʻi's ties to New England through its missionaries and the whaling industry, and the ideological opposition of many to the institution of slavery.

[29][51][52] On August 14, 1862, Pitman left school without his family's knowledge and volunteered to serve in the Union Army and fight in the Civil War.

"[36] Carter described Pitman's rationale for enlisting: "In the midst of the clamor of war, when the very air vibrated with excitement, the wild enthusiasm of the crowds, and the inspiring sound of the drum, his Indian nature rose within him.

He had fallen behind the group because his feet had blistered and swollen due to the tightness of "a pair of thin, high-heeled and narrow soled boots" he had purchased.

One of his comrades temporarily stayed behind to care for him but later decided to move on with the rest of the camp for fear of disciplinary consequences of falling out without authority.

Shortly after he was left, a band of Confederate guerrillas under Colonel John S. Mosby captured the weary and defenseless soldier without a struggle.

[63] The condition of his incarceration including the shortage of food, lack of sanitation, overcrowding and his physical weakness made him susceptible to virulent diseases present in the Confederate prisons.

[42][43] During a prisoner exchange, Pitman was released by the Confederate Army at City Point, Virginia, on December 12, 1862, and then sent to Camp Parole, Annapolis.

[2] Considering him missing, Pitman's regiment did not discover his final fate until news of his funeral at Roxbury was received in the spring of the following year.

Renewed interest in the stories of these individuals and this particular period of Hawaiian-American history have inspired efforts to preserve the memories of the Hawaiians who served in the war.

[30][68][69] On August 26, 2010, on the anniversary of the signing of the Hawaiian Neutrality Proclamation, a bronze plaque was erected along the memorial pathway at the National Memorial Cemetery of the Pacific in Honolulu recognizing these "Hawaiʻi Sons of the Civil War", the more than one hundred documented Hawaiians[note 12] who served during the American Civil War for both the Union and the Confederacy.

[72][73] In 2013, Todd Ocvirk, Nanette Napoleon, Justin Vance, Anita Manning and others began the process of creating a historical documentary film about the individual experiences and stories of Hawaii-born soldiers and sailors of the Civil War, including Pitman, Samuel C. Armstrong, Nathaniel Bright Emerson, James Wood Bush, J. R. Kealoha and many other unnamed combatants of both the Union and the Confederacy.

The history of Hawaiʻi's involvement and the biographies of Pitman, Bush, Kealoha and others were co-written by historians Anita Manning and Justin Vance.