Henry Hoolulu Pitman

Timothy Henry Hoʻolulu Pitman (1845–1863) was the son of a high chiefess of the Kingdom of Hawaii who was among a small number of Hawaiians who fought in the American Civil War. Enlisting in the 22nd Regiment Massachusetts Volunteer Infantry, he served as a private in the Union Army. He was taken prisoner and sent to Libby Prison in Richmond, where he contracted "lung fever" and died shortly after being released on parole in a prisoner exchange.

Early life and family
Timothy Henry Hoʻolulu Pitman was born March 18, 1845 in Hilo, Hawaii, the first son and second child of Benjamin Pitman and Kinoʻoleoliliha. Originally a native of Salem, Massachusetts, Pitman's father was an early pioneer, businessman and sugar and coffee plantation owner on the island of Hawaii, who profited greatly from the kingdom's booming whaling industry in the early 1800s. From his father's side, he was a great-grandson of Joshua Pitman (1755–1822), a English-American carpenter on the ship Franklin under Captain Allen Hallett during the American Revolutionary War. On his mother's side, Pitman was a descendant of High Chief Kameʻeiamoku, one of the royal twins (with Kamanawa) who advised Kamehameha I in his conquest of the Hawaiian Islands, and also of the early American or English sea captain Harold Cox, who lent his name to Keʻeaumoku II, the Governor of Maui. Henry Hoʻolulu Pitman was named after his maternal grandfather High Chief Hoʻolulu, who, along with his brother Hoapili, helped conceal the bones of King Kamehameha I in a secret hiding place after his death. The name Hoʻolulu means "to be calm", as a ship in a protected harbor, in the Hawaiian language. His siblings were Mary Ann Pitman Ailau (1838–1905), Benjamin Keolaokalani Franklin Pitman (1852–1918) and half-sister Maria Kinoʻole Pitman Morey (1858–1892).

The Pitman family was considered quite prosperous and were host to the royal family when they visited Hilo. Besides being one of the leading merchants in town, his father also served the government as district magistrate of Hilo. On the other hand, his mother Kinoʻole had inherited control over much of the lands in Hilo and Ōlaʻa from her own father, and King Kamehameha III had granted her use of the ahupuaʻa of Hilo after her marriage. During his early childhood, the family lived in the mansion that Benjamin Pitman had built in 1840, at an area known as Niopola, one of the favored resort spots of Hawaiian royalty. The Spencer House, as it was called after Pitman sold it to his business partner Captain Thomas Spencer, was later converted into the Hilo Hotel and torn down in 1956. In the 1850s, the family moved to the capital of Honolulu where Benjamin Pitman took up banking and built a beautiful two-storied house which he named Waialeale ("rippling water") at the corner of Alakea and Beretania Streets.

Education
While in Hawaii, Pitman and his older sister Mary attended Mrs. Wetmore's children school in Hilo. The school was located at the Wetmore's residence on Church Street. Taught by Lucy Sheldon Taylor Wetmore, the wife of American missionary doctor and government physician Charles Hinckley Wetmore, the two elder Pitman children received their education in English rather than Hawaiian. This was unusual since Hawaiian was the official language of the Kingdom of Hawaii and all other schools in Hilo were instructed in the Hawaiian language. 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. Like the Pitman siblings, many of their classmates were also of half-Hawaiian (hapa-kanaka) descent with a majority of them being Chinese-Hawaiians (hapa-pake).

After the death of his mother Kinoʻole in 1855, Pitman's father remarried to Maria Louisa Walsworth Kinney, the widow of American missionary Rev. William Kinney. This first stepmother died in 1858 after giving birth to their father's fourth child, a daughter name Maria Kinoʻole (1858–1892). The Pitman family returned to Massachusetts in 1860–1861 where his father remarried to his third wife Martha Ball, giving his four children another stepmother. He continued his education in the public schools of Roxbury, Boston, where the Pitman family lived. According to an 1887 biography written by Robert G. Carter, a private who served in the same company alongside Pitman, he was neglected after his mother's death by his father and stepmother, who "subjected [him] to neglect and treatment, that with his sensitive nature he could not bear."

Growing into adolescence, he was said to strongly resemble his Hawaiian mother. Robert G. Carter gave a brief description of his appearance from wartime letters first published in 1897: "[A] tall, slim boy, straight as an arrow. His face was a perfect oval, his hair was as black as a raven's wing, and his eyes were large and of that peculiar soft, melting blackness, which excites pity when one is in distress. 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. We can look back now and see the shy, reserved nature of the boy, the dark, melancholy eyes, the sad smile, the sensitive twitching of the lips."

American Civil War
After the outbreak of the American Civil War, the Kingdom of Hawaii under King Kamehameha IV declared its neutrality. But many Native Hawaiians and Hawaii-born Americans (mainly descendants of the American missionaries) abroad and in the islands volunteered and enlisted in the military regiments of other states. Hawaiian participants in American wars during its period of independence was not an unheard phenomenon. Individual native Hawaiians have been serving in the United States Navy and Army since the War of 1812 and even more served during the American Civil War. Many Hawaiians personally sympathized with the Union because of New England ties to Hawaii through its missionaries and the whaling industries and the ideological opposition of many to the institution of slavery.

In August 1862, Pitman left school and volunteered to serve in the Union Army and fight in the American Civil War. 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. His resolve was made." Pitman apparently never informed in advance his family about the choice to join the war because his enlistment was reported back in Hawaii as "Henry Pitman has run away from home and gone [to war]." Despite his mix-race ancestry, Pitman avoided the racial segregation of the period. Most Native Hawaiians who participated in the war were assigned to colored regiments, but Pitman's fair skin-color meant he was able to serve in a white unit. However, historian Bob Dye and others claimed Pitman was placed in the colored regiments because of his mixed race despite regiment records which proved otherwise.

Pitman served as a private in the 22nd Regiment Massachusetts Volunteer Infantry, Company H. This regiment was also named the "Henry Wilson's Regiment" after Col. Henry Wilson who commanded the unit in 1861. Col. William S. Tilton was the commander during Pitman's brief term of service. The regiment was part of the V Corps of the Army of the Potomac under the command of Major General George B. McClellan. During this period, it was involved in the Maryland Campaign and fought in the Battle of Antietam, the bloodiest single-day battle in American history, and the Battle of Shepherdstown.

The most detailed account of Pitman's final fate in the War came from Robert G. Carter. In late November 1862, Pitman was captured near Warrenton Junction on the march toward Fredericksburg, Virginia during the weeks prior to the Battle of Fredericksburg. 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 comrade 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. He was urged to move on, but without much success. Pitman's last words to his comrade were, "I will be in camp by night, good by." His fellow soldiers never saw him again and considered him missing. Shortly afterward he was left, a band of Confederate guerrillas under Col. John S. Mosby captured, the weary and defenseless solder without a struggle. The inscription on his tombstone differs from Carter's account, stating he was captured by J. E. B. Stuart's cavalry.

After Pitman's capture, he was imprisoned in the Confederate Libby Prison and Belle Isle in Richmond and, after a prisoner exchange, was sent to Annapolis Parole Camp. Suffering from complications from the condition of his imprisonment, Pitman died at Parole Camp on February 27, 1863 from "lung fever," which was perhaps pneumonia. His remains were returned to his family in Massachusetts. Benjamin Pitman, his father, had his son buried in a family plot in Mount Auburn Cemetery. A grandson of his nephew was named Kealiʻi i Kaua i Pakoma (meaning "Chief that fought the Potomac") in his honor.

Legacy
Shortly after his death, Pitman was eulogized back in Hawaii by Martha Ann Chamberlain, Corresponding Secretary of the Hawaiian Mission Children's Society. "Our cousin, Henry Pitman, the first of Hawaii's sons to fall in the war, died at Annapolis Parole Camp, Feb. 27, of lung fever, serving as a soldier in the Union army. His remains were deposited in Mt. Auburn Cemetery, near Boston, Mass. He died in a just cause. Let his memory be embalmed among our band."

In August 26, 2010, on the anniversary of the signing of the Hawaiian Neutrality Proclamation, a bronze memorial plaque was erected at the National Memorial Cemetery of the Pacific in Honolulu recognizing the "Hawaiʻi Sons of the Civil War," the more than one hundred documented Hawaiians, who served during the American Civil War for both the Union and the Confederacy. Pitman's great grandniece Diane Kinoʻole o Liliha Pitman Spieler attended the ceremony. Pitman Spieler stated, "I'm very proud of a young man of his age — he was quite young — who served in the Civil War for his family." In 2014, Maui based author Wayne Moniz wrote a fictionalized story based on the lives and services of Hawaiian soldiers like Henry Hoʻolulu Pitman during the Civil War in his book Pukoko: A Hawaiian in the American Civil War.

In 2013, Todd Ocvirk, Nanette Napoleon, Justin Vance, and others began the process of creating a historical documentary about the individual experiences and stories of Hawaii-born soldiers and sailors of the American 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.