Timothy Henry Hoʻolulu Pitman was born March 18, 1845, in Hilo, Hawaiʻi, 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 Hawaiʻi, who profited greatly from the kingdom's booming whaling industry in the early 1800s.
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.
On his mother's side, Pitman was a descendant of 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 George "Cox" Kahekili Keʻeaumoku II, the Governor of Maui.
Henry Hoʻolulu Pitman shared his Hawaiian name with his maternal grandfather Hoʻolulu who, along with his brother Hoapili, helped conceal the bones of King Kamehameha I in a secret hiding place after his death.
In the Hawaiian language, the name "Hoʻolulu" means "to lie in the sheltered waters".
His siblings were Mary Pitman Ailau (1838–1905), Benjamin Franklin Keolaokalani Pitman (1852–1918) and half-sister Maria Kinoʻole Pitman Morey (1858–1892).

Because of his father's success in business and his mother's descent from Hawaiian royalty, 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.
Henry's 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 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.
The residence also became known as the Spencer House after Pitman sold it to his business partner Captain Thomas Spencer.
The property later became the site of the Hilo Hotel, built in 1888 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-story house that he named Waialeale ("rippling water") at the corner of Alakea and Beretania Streets.
Timothy Henry Hoʻolulu Pitman was born March 18, 1845, in Hilo, Hawaiʻi, 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 Hawaiʻi, who profited greatly from the kingdom's booming whaling industry in the early 1800s. 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. On his mother's side, Pitman was a descendant of 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 George "Cox" Kahekili Keʻeaumoku II, the Governor of Maui. Henry Hoʻolulu Pitman shared his Hawaiian name with his maternal grandfather Hoʻolulu who, along with his brother Hoapili, helped conceal the bones of King Kamehameha I in a secret hiding place after his death. In the Hawaiian language, the name "Hoʻolulu" means "to lie in the sheltered waters". His siblings were Mary Pitman Ailau (1838–1905), Benjamin Franklin Keolaokalani Pitman (1852–1918) and half-sister Maria Kinoʻole Pitman Morey (1858–1892).
Because of his father's success in business and his mother's descent from Hawaiian royalty, 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. Henry's 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 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. The residence also became known as the Spencer House after Pitman sold it to his business partner Captain Thomas Spencer. The property later became the site of the Hilo Hotel, built in 1888 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-story house that he named Waialeale ("rippling water") at the corner of Alakea and Beretania Streets.
Henry Hoʻolulu Pitman