Henry took to his studies immediately, and once again proved a hard-working and intelligent apprentice. The New Haven community slowly began to realize that this young “heathen,” who in their cultural bias seemed at first so backward and uninspiring, had a huge thirst for knowledge and a heightened capacity to comprehend his teachings. He learned quickly, duplicating the arduous effort placed at the heiau, though many aspects of his training did not come easily.
Since there is no “R” sound in the Hawaiian language, Henry had difficulty pronouncing syllables containing the letter, which often came out like the sound of “L” when spoken in English. Edwin Dwight would repeatedly beseech him, “Try, Obookiah, it is very easy!” Henry took secretive delight whenever Dwight said this and eventually would turn the tables when Henry began teaching his mentor some of the habits and practices of his Native culture, specifically demonstrating to Edwin how to hold water and drink by cupping his hands. Adjusting the thumbs, clasping and bending the fingers together, ‘Opūkaha‘ia made an effective and natural drinking vessel with his hands. When his instructor attempted the maneuver, water dripped through his fingers onto the floor, frustrating the effort. Henry smiled, “Try, Mr. Dwight, it is very easy!”10
Edwin Dwight and others within the Yale community were becoming aware of Henry’s singular ability to entertainingly mimic the mannerisms of people around him. He would challenge, “Who dis?” and start to walk in a distinct style that imitated one of his new-found friends. With gales of laughter, his fellow students knew all the intended victims of Henry’s impersonations. When the New Englanders mimicked ‘Ōpūkaha‘ia’s gait, he fell to the floor laughing, “Me walk so?”11 He was becoming a favorite; his personality, humor, intelligence, and educational zeal endeared him to all he met in New Haven. His friends started to see him not simply as a curiosity from the pagan world, but an entrancing and unique individual with delightful personality characteristics previously unappreciated.
Henry’s intellectual training soon advanced to the point where he requested leave of Brintnall’s family to reside fulltime with the Dwight clan, accelerating his education and improving his chances of getting into an established school. The captain readily gave permission, and Henry moved into the home of the president of Yale College as a servant, continuing his secular and religious training. In Rev. Timothy Dwight’s household, he would be exposed for the first time to a true “praying family morning and evening.”12 It would mark the start of ‘Ōpūkaha‘ia’s sojourn throughout three New England states residing within many Christian households.
The Rev. Timothy Dwight IV had succeeded Ezra Stiles as the eighth president of Yale in 1795, born into a family with many ties to the college. Jonathan Edwards, credited with flowering the First Great Awakening, was his uncle on his mother’s side. Rev. Dwight was an enormous authoritarian figure in the church and college, at times derogatorily referred to as “Pope Dwight.”13 Teaching and the ministry were his vocations with ‘Ōpūkaha‘ia taking on the role of a rather special redemptive focus.
Although ‘Ōpūkaha‘ia did not fully understand all of the Dwight family’s Christian prayers, he could sense that they were at times praying for him and his salvation. They mentioned God to him often in daily conversation though Henry believed “but little.”14 After all, he had been training to become a kahuna, the spiritual conduit of his people where preparation had been intense and instilled with the knowledge of appeasement toward the many gods that controlled existence on the islands and possibly the world, including the lives of his American friends, though they seemed not to realize it. Instead, they prayed to their all-powerful, monotheistic God, strikingly different from the pantheon of Hawaiian akua, who had their own individual sources of authority.
Residing among the Dwight clan, the young “Obookiah” would learn of the “Great Awakenings,” religious revitalization movements that initially appeared in the American colonies during the 1730s. The “First Awakening” shook New England by storm. Powerful preachers like Jonathan Edwards convinced parishioners of their private guilt and the need to seek salvation through personal actions. To experience God in their own way required them to take responsibility for their own spiritual failures and acknowledge them through public penitence. This reduced the need for rituals, replacing the old theology with individual religious conviction.15 The First Great Awakening split the Congregational Church between Old-Lights, who strived to maintain the traditional orthodoxy, and New-Light revivalists attempting to return the church to its “original” orthodoxy.
Then, around the year 1800, an added wave of religious revival took form. While the earlier crusade concentrated doctrine exclusively toward church adherents, the “Second Great Awakening” sought to revitalize declining church memberships by accepting those outside the congregation into the fold, bringing thousands of new parishioners together in anticipation of the Second Coming of Christ, which they believed eminent. Church membership soared throughout New England, creating new denominations and sects. Significantly to Henry, the Rev. Timothy Dwight played an enormous role in helping to create and spread the spiritual resurgence.
The sky opened, cascading a powerful deluge. Lightning pierced the humid afternoon air, sending five young men running for the shelter of a nearby barn. The thunderstorm had disrupted their twice-weekly outdoor prayer vigil by a maple grove. Samuel John Mills, Jr., Harvey Loomis, Byram Green, Frances Robbins, and James Richards sprinted for the protection of the farm building to continue their invocation. Once sheltered from the torrential rain at the lee side of a large haystack, Samuel Mills, namesake and son of a leading Connecticut clergyman and a student at Williams College in Massachusetts, confided to his colleagues his maturing thoughts on spreading the Word of Christ to foreign countries.16
True to the concepts of the Second Great Awakening, Mills saw the necessity for missions to exotic lands: the call to arms to save the souls of the “heathen,” who would burn in hell simply for their lack of knowing the one true God. His companions instantly recognized the “truth” in Mills’ words and decided to band together as “The Brethren,” a secret society devoted to the promotion of the Protestant American foreign missions. Led by Samuel Mills, Jr., the “Haystack Prayer Meeting” participants would commit themselves to sharing their passion and evangelism for spreading the Word of Christ around the world.
While studying with Edwin Dwight, “Obookiah” met Samuel Mills, Jr., soon after the Haystack Prayer Meeting. On completion of his undergraduate work at Williams College, Samuel ventured to New Haven in pursuit of theological studies at Yale and, as a friend of Edwin, was poised to meet the young Hawaiian. Samuel, like many other students, became enchanted by ‘Ōpūkaha‘ia’s charm, envisioning in Henry’s intellect and resolve to learn, the validation of his emerging missionary reasoning. If this “heathen” had the mental capacity to comprehend the Bible, so could other Indigenous Peoples around the world. To Mills, this happenstance introduction to ‘Ōpūkaha‘ia was nothing short of Divine Intervention. If instructed and inspired properly, Mills reasoned, “Henry Obookiah” could serve as the foundation of the missions to his homeland. Samuel’s dreams and aspirations were now collected in the persona of this young Native Hawaiian. To further his ambitions and oversee Obookiah’s conversion, he proposed that Henry reside at his father’s farm in Torringford, Connecticut, to live within the context of a loving Christian home and receive personal instruction directly from the famed Rev. Samuel Mills, Sr.17
Henry’s friends thought the idea wise since they shared concerns that his continual presence in New Haven held the chance of his being kidnapped into the slave trade.18 With consent from Timothy Dwight, Henry willingly moved to the rural northwestern hills of the state in 1810. In Torringford, he would no longer be a personal house servant but instead was taught the work of the farm: cutting wood, pulling flax, and mowing hay for the Rev. Mills and his family, who found ‘Opūkaha‘ia “a remarkable youth.”19 He immediately felt welcomed and loved within the Mills’ household—“It seemed to me as my own home.”20
The physical journey of ‘Ōpūkaha‘ia extended