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Flynt, who succeeded the hapless Daniel Rogers as Jacob’s tutor, agreed that Whitefield’s visit was a success. He found Whitefield “affecting in his delivery,” a “good man [who is] sincerely desirous to doe good to the souls of Sinners.” Harvard’s students, Flynt reported, were tremendously moved and shaken by Whitefield: “Many Schollars appeared to be in great concern as to their souls and Eternal State.”⁴³

      Yet, thanks to Harvard’s irreligious ways, Whitefield’s appearance was controversial. The Great Awakener himself thought little of Harvard. “Discipline,” Whitefield confided in his journal, “is at a low ebb” at the college: “Bad books are become fashionable among the tutors and students. Tillotson and Clark are read, instead of Shepard, Stoddard, and such-like evangelical writers.” When Harvard’s faculty members learned of Whitefield’s criticisms, they were stung. His plans to return to New England in 1744 prompted them to publish “The Testimony of the President, Professors, Tutors, and Hebrew Instructor of Harvard College, against George Whitefield.” The essay condemned Whitefield on several levels—as a man (he was “an Enthusiast, a censorious, uncharitable Person, and a deluder of the People”); as a danger to organized religion (“he is presently apt to run into slander, and stigmatize them [ministers] as Men of no religion, unconverted, and Opposers of the Spirit of God”); and as an itinerant (“we apprehend this Itinerant Manner of preaching to be of the worst and most pernicious Tendency”). These critics at Harvard came to oppose the Great Awakening as a regressive and backward-looking movement, and their stance was another sign of the college’s growing liberalism. It demonstrated how Harvard was becoming more latitudinarian, and more Armininian, than Yale.⁴⁴

      Jacob’s position in the college’s growing rift between “liberal” Arminians and “traditional” Calvinists was no mystery—he was thunderstruck by Whitefield’s performance and supported him: “I heard him with wonder and affection, and approved highly of his preaching and conduct.” Green at this young age wholeheartedly backed the goals of the Great Awakening—to spark a resurgence of piety—and he agreed completely with Whitefield’s harsh assessment of Harvard. For Jacob, it was obvious that Harvard’s staid religious scene needed shaking up.⁴⁵

      In fact, he and some other members of the Harvard community were so excited by Whitefield’s preaching, and felt so strongly about what he was trying to achieve during his New England appearances, that they followed him to neighboring Massachusetts towns as he continued on his tour. Among this Harvard contingent was Daniel Rogers, the unpopular tutor of Jacob Green’s who had faced ridicule from students and teachers alike.

      In September 1740, Rogers still harbored dreams of preaching, and Whitefield’s tour inspired him to take to the field. This, at last, was his chance to make a real difference in religion and to win a preaching position, and when the great George Whitefield himself asked Rogers to itinerate he enthusiastically concurred. The college authorities were not happy with his decision—Rogers was abandoning his students for a New Light itinerant, and they asked him to return to the classroom or to resign. Rogers did neither at first, explaining “that the blessed Spirit of God has led me out; and how far I shall proceed He only knows.”⁴⁶

      Like Rogers, Green dropped what he was doing in late September and followed Whitefield as he made his way across Massachusetts. Whitefield’s first stop after Cambridge was “Mr. Foxcroft’s meeting-house,” where the Great Awakener preached before a packed crowd. The next stop was an appearance at Roxbury before “many thousands.” For Jacob, the places, and the days, must have blurred as Whitefield kept up his punishing pace: Marble Head, Salem, Ipswich on September 29; Ipswich, Newbury, and Hampton on September 30; York and Portsmouth on October 2—and on and on, into mid-October, including a stop at Malden, where Jacob had been born and lived for so many years. Green witnessed firsthand some of the most stirring appearances of the 1740 tour, including Whitefield’s October 12 visit to Boston. Accompanied by the Massachusetts governor, Whitefield recounted how he preached his “farewell sermon [at the Boston Common] to near twenty thousand people,—a sight I have not seen since I left Blackheath [England],—and a sight, perhaps never seen before in America.”⁴⁷

      Jacob made it as far as Leicester, which Whitefield visited on the afternoon of October 15. Green was apparently fatigued and homesick at this point—Leicester was in western Massachusetts, about six miles from Worcester, and not too far from Killingly, Connecticut, where his mother lived. She was seriously ill (indeed, she would die in December 1741), and Jacob left Whitefield to visit her. As it turned out, this was the last time he saw her.⁴⁸

      As momentous as Whitefield’s tour was, the arrival of Gilbert Tennent only a few months later made an even deeper impression on Jacob. Tennent came to Cambridge in late January 1741. Uncouth, haughty, and loud, Tennent was not Whitefield’s equal in speaking ability or intellect, but he stirred Jacob in ways that Whitefield did not. Part of Tennent’s influence on Jacob had to do with the timing of his visit on that cold January day, and part of it with the message he delivered. Jacob had never heard of Gilbert Tennent when this controversial Presbyterian itinerant came to Harvard, and he went to hear him only out of curiosity. Tennent’s sermon was on false hope. “Some of you may try to maintain your old hope, though it shakes and has no foundation, and you will flatter and deceive yourselves,” Jacob recalled him saying. “But your hope must come down. I know it will be like rending soul and body asunder, but down it must come, or you must go to hell with it.”⁴⁹

      These words struck Green with tremendous force. Every doubt he had long harbored about his spirituality, every fear he had long felt about his eternal fate under the Calvinistic doctrine of predestination, came washing over him as Tennent shouted his warnings from the pulpit. The sermon left Jacob deeply upset and troubled: “I saw myself fit for hell. The sinfulness of my heart and nature appeared infinitely more dreadful than ever it had done before. I had a new and dreadful sense of my wickedness.” To his friends and acquaintances, Jacob was serious and hardworking, but Jacob still viewed himself as a wretched sinner. His childhood feelings of inadequacy tormented him. As a young boy raised in the Calvinistic gloom of Puritanism and the dire warnings of Michael Wigglesworth’s Day of Doom, Jacob was convinced that he was unsaved and a sinner in the eyes of God. These doubts grew and became more specific as he got older.⁵⁰

      Before he entered Harvard, two incidents had crystallized his sense of crisis and persuaded him that he was going to hell. The first occurred at about age sixteen, when he left Leicester for the fifteen-mile ride to Killingly to see his mother. The trip entailed passing through a “gloomy wilderness” containing few houses. Jacob was unfamiliar with the trail, and he attempted to navigate it as night and rain arrived. When the path forked, Jacob took the wrong turn. Engulfed in blackness, Jacob was unable to find his way back. “What to do I knew not,” he recalled. “Sometimes I moved onward, sometimes [I] stopped and considered; but generally kept moving on.” Pelted by rain, tired and hungry, Jacob became scared and “my conscience fell upon me.” His feelings of sinfulness resurfaced, and he prayed to God for forgiveness. “I confessed my sins and omissions,” and he vowed to change if God “would deliver me out of that wilderness.” Jacob also made his promise as specific as possible: “I would, within one week after I got home from that journey, begin to pray in secret evening and morning, and continue to do so for a fortnight.”⁵¹

      Appropriately bucked up, Jacob gave his horse a kick and pressed on in the rain. Almost immediately, he spied a light ahead and moved toward it. It was a house occupied by a family, who provided him with directions. They also agreed to allow a boy to help guide Jacob out of the woods. Thanks to the boy’s help and the moon’s emergence from behind storm clouds, Jacob finally made it to his mother’s house shortly after midnight.

      Jacob felt great relief at his deliverance, but he reneged on his promise to begin praying. With each passing day “I was less and less affected with a sense of my being lost in the woods, and the promise I had made.” He returned to Malden feeling “careless, stupid, and insensible of my guilt.” Jacob, of course, felt great guilt at his failure to keep his word to God. His guilt was so intense, it led to the second incident: on the night before he was supposed to begin praying regularly, he suffered a violent nightmare that left him even more afraid for his soul.⁵²

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