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Chapter One
"As Subtil & Deep as Hell Itself": Nathan Hale and the Spying Game
The Yankee soldier, flinty once but now wizened and gnarled, flashed in and out of lucidity. Sometimes his memories of a war fought sixty years before gushed liberally from his lips, but more often, for half hours at a time, he would slouch in vacant-eyed silence. His visiting relative, R. N. Wright, recorded despondently that Asher Wright "is now in the eighty-second year of his life, and besides the infirmities of advanced age, has been affected in his mind, ever since the melancholy death of his young master, Captain Nathan Hale. What is gathered of him, can be learnt only at intervals and when he is in the humor of conversation."1
One evening in 1836, though, Asher was particularly loquacious, and spoke so excitedly his companion taxed himself hard to scribble down the old man's words. Wright the Younger used whatever came to hand—a blank leaf in the book he had been reading (Hume's History of England, as it happened)—for he knew that he was listening to one of a diminishing band of brothers of the Revolutionary War. Indeed, Asher was a particularly venerated member of that generation: Not only one of the few remaining men who had known the legendary Captain Hale, Asher Wright was also the last surviving Patriot to have seen Hale alive. He had shaved and dressed him on the very morning of his departure.2
"When he left us, he told me he had got to be absent a while, and wanted I should take care of his things & if the army moved before he returned, have them moved too. . . . He was too good-looking to go so. He could not deceive. Some scrubby fellows ought to have gone. He had marks [scars] on his forehead, so that anybody would know him who had ever seen him—having had [gun]powder flashed in his face. He had a large hair mole on his neck just where the knot come. In his boyhood, his playmates sometimes twitted him about it, telling him he would be hanged."
One of those playmates might well have been Asher Wright. A local boy, he had grown up with Hale, but they had parted ways after Nathan went off to Yale, a place far beyond the modest means of Wright's family. They met again during the war, when Hale's first "waiter," his servant, had fallen sick, and though the man eventually recovered (Wright ascribed it to Hale's practice of praying for him), he could not continue in the post. "Capt. Hale was [of] a mind I should take his place," recalled Wright, "And I did & remained with him till he went on to Long Island."
Tired of his exertions, Wright could add little more to his recollections—apart from one nugget. Nathan Hale, today immortalized as the "Martyr-Spy of the Revolution," wasn't even supposed to have become a spy in the first place. "James Sprague, my aunt's cousin . . . he was desired by Col[onel] Knowlton, to go on to Long Island. He refused, saying, I am willing to go & fight them, but as for going among them & being taken & hung up like a dog, I will not do it." No soldiers, let alone officers, in Knowlton's Rangers—Hale's regiment—wanted to take the ignoble job of secret agent, an occupation considered inappropriate for gentlemen, and one best suited for blackguards, cheats, and cowards. And it was then, remembered Asher, that "Hale stood by and said, I will undertake the business."3
Born on June 6, 1755, the sixth child in a large family, Nathan Hale was of good and middling, and most respectable, Connecticut stock. The first Hale—one Robert, reputedly descended from a knightly family in Kent—arrived in Massachusetts from England in the early 1630s, and turned his hand to blacksmithing. He was evidently an assiduous one, for he managed to acquire several fields along the Mystic River. His son John attended the newly founded Harvard College, graduating in 1657 and becoming a Calvinist pastor of robust persuasion near Salem, where he participated in the witch trials but later recanted his temporary insanity. One of John's sons, Richard—Nathan's father—left for Connecticut in about 1744 and settled in Coventry, twenty miles east of Hartford, where fertile farming land was still to be had. On his mother's side, Nathan was descended from Elder John Strong, an immigrant who sailed aboard the Mary and John in 1630 from Plymouth. It was his great-great-granddaughter, Elizabeth, who married Richard and begat Nathan.
As was only to be expected of strict New England Congregationalists, Nathan was taught to revere magistrates and ministers as God's chosen servants, and to observe each Sabbath as if it were his final one on this earth. He pronounced grace thrice daily, attended church twice on Sundays, and declaimed prayers once before bed.
When Nathan was twelve, his mother died, and the Strongs took his education in hand. As there were several men of the cloth on the Strong side, Nathan was marked down for a clerical career, for which a college education was essential. In preparation for his entry to Yale—where the Strongs had connections—Nathan had Cicero, Cato, and Horace beaten into him by the Reverend Dr. Huntingdon, a man of pronounced liberal tendency, who, in between his classes on Latin declensions and conjugations, subjected Nathan to a series of jeremiads on the iniquity of the Stamp Act.
By the summer of 1769, young Hale, all of fourteen, was at last ready to go up to Yale. Along with thirty-five other promising teenagers, he entered that September as a member of the Class of '73 (there were about one hundred students at the college). For freshmen, Yale could be a most forbidding and mystifying place, a Bedlam of confusing rituals and hierarchies where no rule could be bent, no corners cut, no blind eye turned. A fearsome regime of fines, ranging from a penny (for missing mandatory chapel services) to twelve shillings for graver misdemeanors (missing them twice), ruthlessly controlled the pupils' behavior. Every student doffed his hat when the president approached, and bowed as he passed, or faced his wrath. Freshmen, meanwhile, acted as flunkies for the upperclassmen, who exacted a very painful form of punishment on those unwise enough to tell them where to go.
The first priority, apart from striving to avoid attracting an upperclassman's attention, was work. Hale imbibed a curriculum of Hebrew, Latin, Greek, logic, rhetoric, disputes, geometry, classics, natural philosophy, divinity, astronomy, mathematics, metaphysics, and ethics. Roger Alden, a good friend of his, told Hale that he dreaded the curriculum as much as he did "the morning prayer bell or Saturday noon recitations." That prayer bell rang at 4.30 a.m. in the summer, and at 5 a.m. in the winter; as for the Saturday recitations, terrified pupils were interrogated by their tutors in the three classical languages.4
Still, college days were not all drudgery. Hale evidently managed to have a good time. His father, confronted with mounting bills for Nathan's living expenses, instructed him in December 1769—just three months after his once-studious boy arrived in New Haven—to "carefully mind your studies that your time be not lost." He also asked his errant son to remember to attend chapel to avoid more fines. A year later, Hale Senior heard that Hale minor was not minding his studies as carefully as he ought, and anxiously urged him to "shun all vice, especially card-playing." (Yale students, if caught three times gambling, were expelled from the college.)
One baleful influence on Hale was his classmate Benjamin Tallmadge, the son of a churchman who had diligently taught him his Virgil and Plato. He had more time for mischief making than his peers, for, as Tallmadge self-mockingly wrote in his memoirs, "being so well versed in the Latin and Greek languages, I had not much occasion to study during the first two years of my collegiate life."5 In March 1771, Tallmadge, Nathan, and Nathan's older brother Enoch (also attending Yale) were fined heavily (a shilling and five pence) for breaking windows following a prolonged visit to a local tavern. Tallmadge, who had drunk deeper of the amber nectar than the Hales, was amerced another seven pence for additional damage to college property.6
Students entertained themselves. Debating societies were always popular: In 1773, for example, Hale and Tallmadge debated the motion "Whether the Education of Daughters be not, without any just reason, more neglected than that of sons." (They argued for the pro-daughter side, and won, an event that James Hillhouse, a Yale contemporary, said "received the plaudits of the ladies present.")7
He was a member of the Linonia, the most "social" of the debating clubs, and it was noted in the minutes that the meeting of December 23, 1771, "was opened with a very entertaining narration by Hale." Hale also took part, with relish, in amateur theatrical productions; contemporaries thought him excellent in Robert Dodsley's frothy farce The Toy Shop (a hit on the London stage in 1735). When they weren't arguing or acting, the students joined such literary societies as the Brothers in Unity, whose members adopted nicknames derived from classical myth (Hale chose Damon, while Tallmadge went with Pythias). Ostensibly, they intended to improve their rhetorical writing style, but all too often, being bored with the starchy formality of Latin, they fell into the kind of flowery purplishness popular at the time in artistic circles in England and America.8
A letter from Tallmadge to Hale gives an indication of the predominant style: "Friendly Sir, In my delightsome retirement from the fruitless bustle of the noisy, with my usual delight, &, perhaps, with more than common attention, I perused your epistle—replete as it was with sentiments worthy to be contemplated, let me assure you with the strongest confidence of an affectionate friend, that with nothing was my pleasure so greatly heightened, as with your curious remarks upon my preceding performance, which, so far from carrying the appearance of a censuring critick's empty amusement, seemed to me to be wholly the result of unspoted regard & (as I may say) fraternal esteem."9
Tiresome to read today, but the letter, and the several others like it between the two men, signals how immensely fond Tallmadge and Hale were of one another. Leafing through their correspondence, it's still touching to read the encomiums "I remain your constant friend" and "a heart ever devoted to your welfare."10 If anything malign ever happened to one, the other would be merciless toward his assailants.
Thus, Yale of the 1770s, despite its addiction to protocol and pomposity, was a place where comradeship and camaraderie flourished. Paradoxically, too, the college inspired a rebellious, insubordinate ethos, not least when its inmates frequently (and loudly) complained about the dire food served in hall and the usurious cost of books for sale. On no other issue, however, were the students more agitated than that of relations with the Mother Country. In the years before the Revolution, Yale was notorious for its politics. Afterwards, one fierce Loyalist, Thomas Jones, recalled bitterly of his alma mater that it was nothing but "a nursery of sedition, of faction, and republicanism," while General Thomas Gage, commander of the British forces in North America, branded the place "a seminary of democracy" full of "pretended patriots."11 For all Gage's disparagement, Yale students were the first American students to organize a boycott against British-made goods, and when Hale was entering, the graduating class voted almost unanimously to appear "wholly dressed in the manufactures of our own country" at their commencement ceremony.
Upon graduation, Hale was obliged to find a job, the clerical life having lost whatever attractions it may once have had. He became a schoolmaster in East Haddam (Tallmadge taught in Wethersfield), a town sixteen miles from the mouth of the Connecticut River, in the fall of 1773. The school was rather small, and worse, isolated, and still worse, paid poorly. Even had the wages been sufficient, there was nothing in East Haddam to spend it on. He boarded with James Green: His descendants were reported some time ago to possess the only chair that Hale is known to have sat upon. Unsurprisingly, considering that East Haddam's nightlife consisted of sitting on chairs, Hale was bored numb, mentally as well as physically. By March 1774, he couldn't bear it any longer and applied to New London, to the Union School, a wealthy private academy.12
In the meantime, he fell in love. Or rather, re-fell in love, with the same woman. In his last year at college, Hale had been introduced to Alice Adams, a pretty, vivacious thing, but one, alas, about to be married off to a wealthy man, Elijah Ripley, considerably older than herself. Fortunately for Hale, Mr. Ripley's talents did not include longevity, and he died on December 26, 1774. Hale waited, decently, until her period of mourning was over before launching his suit. In early 1775, Alice was overjoyed to receive a Hale-penned poem:
Alicia, born with every striking charm,
The eye to ravish or the heart to warm
Fair in thy form, still fairer in thy mind,
With beauty wisdom, sense with sweetness joined
Great without pride, and lovely without art. . . .
The two began to court, but Hale put duty before pleasure.13 Just a few months into his wooing, the Revolution came to Connecticut. The battles of Lexington and Concord on April 19, 1775, galvanized young men into joining the colors—including two of Hale's brothers, who signed up for the Connecticut militia marching to Massachusetts. Of the thirty-five members of Yale's 1775 class, for instance, thirteen continued into the ministry, but no fewer than thirteen others joined the Continental army.14
Inescapably shaped by his background, his milieu, and his education, Hale was by temperament and inclination a pronounced Patriot. Tallmadge, who wrote to him on July 4, 1775, allows us a penetrating glimpse into what two young American idealists felt at the time: "I consider our country, a land flowing as it were with milk & honey, holding open her arms, & demanding assistance from all who can assist her in her sore distress. . . . [W]e all should be ready to step forth in the common cause."15
While Tallmadge would join the Continentals the following year, Hale went to the recruiting station just two days after that inspirational letter was written. It was the same day—July 6—that the governor of Connecticut commissioned officers in the newly raised Seventh Regiment. Hale's name is on the list as first lieutenant of the third company. The Seventh was commanded by Colonel Charles Webb, whose own first lieutenant was William Hull, one of Hale's friends from Yale. On September 8, Washington requested Governor Jonathan Trumbull to send his new Connecticut regiments, and within two weeks, Hale was on the march. From his diary—albeit abbreviated, and hurriedly jotted down—we know that the Seventh marched to Providence, then through Massachusetts to Cambridge, headquarters of the American forces surrounding Boston, where they had Gage and his forces bottled up. Once there, the regiment was assigned to General John Sullivan's brigade at Winter Hill; Hale was promoted to captain-lieutenant, and signed up for another contract of service for 1776 at a time when many refused to reenlist when their terms were up. His regiment was then renamed the "Nineteenth Foot in the service of the United Colonies," as part of Washington's effort to mold his gaggle of ragtag militias into a professional volunteer force.
