On December 2nd, 1829, Oahu’s fifth governor Boki Kamāʻuleʻule set sail on the Kamehameha to obtain sandalwood on Erromango, an island in Vanuatu. Boki’s expedition included two ships and nearly 600 people; it returned with one ship and roughly 20 people. Boki was one of the several hundred men who died on the journey.

Boki occupies an interesting intersection of Hawaiian history. Historian Gavan Daws wrote that “Boki’s experience was Hawaii’s in miniature.” He was perpetually caught between traditional and foreign cultures. He and his brother Kalanimoku were the first Hawaiian chiefs to get baptised as Christians, and at times he appeared to be a devout believer — often when it was politically advantageous — but he was mostly known as a drinker and gambler. He refused to learn English and took singular stands against haole cultural influence on occasion, but also eagerly used his position as governor to participate in several haole industries such as sugarcane, sandalwood, and prostitution. He was a living homage to the old ways and an ominous premonition of the imminent changes Hawaii would undergo,  beloved by the people and loathed by virtually everyone in positions of power, from missionaries and foreign dignitaries to fellow chiefs and Hawaiian monarchs. 

Born at the end of the 18th century, Boki was the son of a chief and the great grandson of Maui’s King Kekaulike. He was appointed as the chief of Waianae and the governor of Oahu by King Kamehameha I, a post that was continued under King Kamehameha II, Liholiho. Boki and Liholiho quickly struck a close bond, a friendship forged through excessive drinking and royal merriment. Boki and his wife Kuini Liliha accompanied the king on his trip to England where he caught measles and died. They returned together on the British frigate HMS Blonde, after which Boki would eventually name his hotel-turned-tavern-turned-brothel. 

Boki’s British experience made him something of a celebrity upon his return. He regularly wore a British military dress uniform to social gatherings, charming chiefs and commoners alike with stories of London’s opera, ballet and theater. However, the death of Liholiho — who was never a part of a Christian church — ushered in a new era of daily life. In Liholiho’s absence, Kaʻahumanu assumed monarchical control of the islands and soon instituted new laws based on Christian morals. Boki appeared to be a somber supporter of these laws, which were based off the 10 Commandments and included bans on alcohol, gambling and adultery on top of requiring Hawaiians to attend Sabbath church services. But Boki, being who he was, eventually took his habits to the shadows. When sailors were driven to revolt at the dearth of drinks and prostitutes to welcome them, Boki set up a secretive billiards room where drinking, gambling and prostitution thrived. He also arranged boats of women to board the docked ships at night, taxing the traffic for his own personal gain. When confronted by missionaries, Boki defended the practices and stopped attending church.

“We have long suspected Boki’s professions of piety have little solid foundation,” wrote missionary Elisha Loomis. “We are glad he has . . . come out boldly for it is best men should be ranged under their proper colors . . . We are glad Boki no longer labors in disguise.”

Meanwhile, Boki’s relationship with his brother Kalanimoku was straining. Kalanimoku had become an exemplary Christian in the eyes of the missionaries, and he firmly backed the morality laws that Boki flouted for profit. When Kalanimoku died, Queen Kaʻahumanu fined Boki and his wife for misconduct, intemperance, fornication and adultery. 

“By the end of 1829,” Gavan Daws writes, “[Boki] was beaten at every turn.” He was shunned by the religious elite; mocked by foreign dignitaries (French navigator Louis de Freycinet called him an “Ignoble Savage” and an “inert mass” whose constant drunkenness made him a “tool of American merchants”); and soundly defeated by the superior statecraft of Kaʻahumanu. His sugarcane plantation had tanked, and he was saddled with sandalwood debt to the tune of $70,000-$140,000 — between $2-$4 million in today’s money.

A seemingly happy accident occurred in November, 1829. A ship from New South Whales arrived in Honolulu with word of an island rich in sandalwood. Boki arranged to be the director and chief navigator of the expedition, loading up 600 men on two ships, the Kamehameha and the Becket. Boki traveled on the Kamehameha, which was lost at sea for reasons still unknown. The Becket made it to its destination, but was met by hostile island natives. Many who survived the bloody conflict fell ill and died. The Becket and its remaining crew of 20 arrived back in Honolulu in August, 1830. 

Missionaries claimed Boki’s demise was divine judgment for his immorality, but the common people of Honolulu mourned his death. A year later, a man claimed he saw Boki at the helm of a warship off the Waianae coast. “The people were in an uproar, some frightened, some pleased,” wrote the native historian Kamakau. It turned out to be false, and the man was publicly whipped. Even after his death, Boki was simultaneously the source of dread, hope and pain for Hawaiians.