Courtship at the Constitutional Convention

COURTSHIP, n. 1. The act of soliciting favor. Swift. 2. The act of wooing in love; solicitation of a woman to marriage. Dryden. 3. Civility; elegance of manners. Obs. Donne.

After finishing a series of lectures in Albany, Webster returned to Connecticut, arriving back in Hartford on May 27. Two days later, he dined with Joel Barlow. On May 30, he rode on to the West Division and was reunited with his family. That evening, he wrote in his diary, “Meet my friends with joy.”

Webster immediately made arrangements to take his lecture tour around his native New England. His primary objective was to raise the funds needed to print new editions of The Grammatical Institute. And by fraternizing with the community leaders and school officials who attended his talks, as well as the booksellers who sold the tickets, he also hoped to boost sales. While Webster would still focus on the future of American education, he would now also share the experiences and factoids that he had gathered during his visits to other parts of the country. He decided to start in his hometown. On June 5, he placed the following ad in The Connecticut Courant: “Mr Webster will read some remarks on the government, the population, agriculture, literature, slavery, climate and commerce of the United States; exhibiting a comparative view of each of those views in the eastern, the middle and the southern states; with some observations of manners.” At the North Meeting House the following evening, Webster was rudely interrupted. Angry that he had provided free tickets to members of the state legislature, but charged an admission fee to everyone else, a contingent of local farmers mobbed the Presbyterian church, breaking a few windows. Having climbed to the top of the social ladder, Noah Webster, Jr., was now viewed with envy and contempt by those who, like his father and two brothers, spent their lives toiling in the fields. The antipathy went in both directions. “Let it be remembered,” Webster wrote in his diary, “that in the year 1786, there are people in Hartford so illiberal, that they will not permit public lectures to be read in a church because they cannot be admitted without paying two shillings.” Over the next two nights, he completed this brief lecture series in more friendly confines—Mr. Collier’s dance studio. But only a few friends showed up.

Webster fared better in New Haven, where he was also pleased to reconnect with Ezra Stiles and Josiah Meigs. After counting New Haven’s four hundred houses on Saturday, June 17, he gave the first of his six well-attended lectures at the state house the following Monday. On June 30, he delivered his last lecture “avec éclat.” That same day, in a letter to Pickering, he quantified exactly how this reception compared with what he had experienced elsewhere: “In New Haven, I have about 70 hearers . . . a greater number in proportion to the size of the town than I have had before.”

Though publicly Webster was animated, in private he was feeling despondent. Upon his return to Hartford in early July, he reported being “oppressed with vis inertiae” [the force of inertia]. Caught in what he perceived to be a never-ending search for a wife, he was also spiritually adrift. While attending a Quaker meeting during his next round of touring, he recorded the following mental meanderings: “Not a word spoken . . . a whisper or two among the Ladies excepted, I was very attentive to the silent exhortations of a pretty girl of sixteen. Such blushes, such lips made one feel devotion.” And summing up another silent meeting a day later, he reported, “Saw a sweet girl.”

Over the next four months, Webster’s barnstorming took him to Boston (twice), Salem, Portsmouth, Newburyport, Providence and Newport. Webster was disappointed with the typically low turnouts. The one bright spot was a subscription lecture before ninety literary men—including the revolutionary journalist turned state senator, Samuel Adams—at Faneuil Hall on his second trip to Boston. And Webster was honored that Franklin himself had acknowledged the importance of his efforts. In response to Webster’s June 23 letter, the Doctor wrote back on July 9: “I think with you that your lecturing on the language will be of great use in preparing the minds of people for the improvements proposed, and therefore would not advise your omitting any of the engagements you have made, for the sake of being here sooner than your business requires, that is in September or October next. I shall then be glad to see and confer with you on the subject.”

Webster’s lectures, which had started out as supplements to his own Grammatical Institute, had evolved into a prologue for his upcoming collaboration with Franklin. But with Franklin at the height of his national fame, Webster didn’t mind second billing.

In Salem, Webster crossed paths with John Gardner, a South Carolina businessman who had accompanied him on his first house-count in Baltimore back in September 1785. The two statistically obsessed men pooled their data on America’s housing stock. A nephew of Timothy Pickering, Gardner was proving to be a dedicated sidekick. On June 16, as a wave of fires ravaged Charleston, Gardner had exhorted Webster, “I am much obliged to you for the return of the houses of the several towns in your letter. . . . I must request you to persevere in counting houses wherever you have leasure [sic].” In that same letter, Gardner, whose family’s fortune would be funneled into Boston’s Gardner Museum a century later, also offered his immediate assessment of the conflagration’s impact on his Charleston tally: “The number stood 1560 but was yesterday reduced 19 by a terrible Fire which broke out near Broad Street.” Buoyed by their meeting in mid-August, Webster was more dedicated than ever to completing this national survey.

As he traveled around Massachusetts that summer, the discontent of the state’s farmers reached a fever pitch. The previous year, the Bay State had enacted a new tax of a pound per poll (head), which was roughly four times the rate of its New England neighbors. Also burdened by declining land prices, the aggrieved denizens of rural Massachusetts demanded that the state government print paper money. Considering the rebels morally reprehensible, Webster repeatedly mocked their so-called grievances. On August 14, Webster wrote Pickering from Salem, “The best way to redress grievances is for every man when he gets a sixpence, instead of purchasing a pint of rum or two ounces of tea, to deposit his pence in a desk, till he has accumulated enough to answer the calls of the collector.”

A couple of weeks later, a band of farmers in western Massachusetts, led by Daniel Shays, took up arms. The next month, the movement that later became known as “Shays’ Rebellion” shut down the state supreme court in Springfield, which had been sending scores of debt-ridden farmers to prison. Webster the businessman would have to start making concessions to the economically distressed rural New Englanders. In its ads for his books at the end of that summer, his publisher Hudson and Goodwin noted that in lieu of cash, it would also accept “grain of any kind, bees-wax or flax.”

However, the popular unrest was making Webster so uncomfortable that he now felt it necessary to abandon New England. On September 14, as he was winding up his second visit to Boston, he wrote a friend, the New York merchant James Watson, “In the course of autumn, I shall take up my bed and walk out of Connecticut. . . . These eastern states are in tumult.” Noting that “I am the son of a New England farmer—an honest man,” Webster stressed that the disposition of the current generation of New Englanders is “not natural—it is all habit and the effect of credit.” Waxing nostalgic for a past that never was, he argued that repayment of debts should be simply a matter of honor. Webster’s moralistic stance heaped the blame solely on the victims of America’s struggling economy.

While lecturing in Providence in late September, Webster learned that mobs were also forcing the hand of the Rhode Island legislature, which had recently authorized the printing of a hundred thousand dollars. He was terrified that chaos would reign. In a piece published on September 28 in Providence’s paper, The United States Chronicle, under the byline “Tom Thoughtful”—an allusion to “Tom Brainless,” the bumbling protagonist of Trumbull’s “The Progress of Dulness”—Webster released his pent-up anxiety and rage. “My countrymen,” he wrote at the top of this editorial, “the devil is in you”; he then proceeded to use this harsh refrain like a whip. But before doing so, the future lexicographer carefully defined his key term: “the effects ascribed to this prince of evil spirits. . . . I ascribe to the wickedness and ignorance of the human heart. Taking the word ‘Devil’ in this sense, he is in you and among you in a variety of ways.” Webster found evidence of the devil in the farmers’ inability to trust Congress, their thirst for swift action and their love of luxury. But the whole country was also at fault. “The weakness of our federal government,” he insisted, “is the Devil.” As in his Sketches, Webster here, too, alluded to the necessity of a “supreme head.” For Webster, a stronger union was necessary to give America the exorcism it desperately needed.

After completing his lecture tour in the eastern states, Webster returned to Hartford on October 27. But he was too broke to head directly to Philadelphia as he had hoped. The following day, he bared his financial soul to Franklin: “I labor under some embarrassments which I take the liberty to mention to your Excellency. The profits on the sale of my books, which amount now to £100 per annum, are all appropriated to reimburse the expense I have incurred in prosecuting my designs, so that I cannot with propriety expect any assistance from them for the coming year. My lectures, which have supported me hitherto, are closed; and I have nothing to depend on for subsistence this year but my further exertions in some business.”

Webster asked Franklin for help in tracking down some prospects in Philadelphia: “I shall wait here a few days for your Excellency’s answer, if an answer will not be too great a trouble; for in my present situation I know not how to act.” Though he never received a response from the Doctor, Webster soon summoned up the courage to head south. Not only was he eager to consult with Franklin, who that November was unanimously reappointed president of Pennsylvania, but the forces of history were also tugging at him. Less than two months earlier, the Annapolis Convention had issued a report, then circulating throughout the country, which recommended that Congress meet on the second Monday in May to strengthen the Articles of Confederation. Once again Webster would trust his own resourcefulness. He spent the next few weeks settling his affairs and saying goodbye to family and friends, including Joel Barlow, John Trumbull and Nathan Perkins. He also dashed off a couple of editorials stressing the need for national unity. In an anonymous piece, which ran in the Courant on November 20, he cast his opponents as simpletons: “But the anti-federal men think as they have been bred—their education has been rather indifferent. . . . Besides most of them live remote from the best opportunities of information.” Three days later, on Thanksgiving Day, Webster left Hartford “to seek a living, perhaps for life.”

WEBSTER WOULD ONCE AGAIN travel to Philadelphia by way of New Haven and New York. In New Haven, he gave two more lectures at the state house. In a series of lively dinners and teas, he also discussed the national crisis with Yale President Stiles and his former classmate Meigs, as well as with Roger Sherman, the longtime congressman recently elected the town’s first mayor, who, according to Thomas Jefferson, “never said a foolish thing in his life.” While his colleagues urged more sympathy for the embattled farmers, Webster held to a hard line. Huddling in his room to avoid the single-digit temperatures and violent snowstorms, he fired off an anonymous editorial, “A Bit of Advice to Connecticut Folks,” published in Meigs’ New Haven Gazette on December 14. Attempting to solve America’s economic problems with a statistical sleight of hand, he began, “It is hard times—money is scarce—taxes are high—and private debts push us. What shall we do? Why hear a few facts; stubborn facts,—and then take some advice.” Webster’s facts consisted of two sets of numbers: Connecticut’s “necessary expenses” and its “unnecessary expenses.” The big-ticket items in the first category included the salaries of state officials (e.g., the annual hundred pounds for each of its two hundred clergymen), the cost of maintaining its five hundred schools and support of the poor (“very necessary”). In the second category, the once and future attorney placed the eighteen thousand pounds the state spent on lawyers. But by far the biggest waste came from the ninety thousand pounds Connecticut citizens spent on rum. Webster’s cure was simple: avoid lawyers’ fees and drink. “My countrymen,” he concluded, “I am not trifling with you; I am serious. You feel the facts I state.” Confident of the wisdom contained in his balance sheets, Webster would reprint this essay a half-dozen times over the next decade.

In New York, Webster ended up giving just one lecture. Attracting much less interest than before, he spoke not at city hall, but at the Queen Street studio of one of the nation’s leading dancing masters, John Hulett, with whom Webster would develop close ties. During his next sojourn in New York a year later, Webster would “take a few steps in dancing under Mr. Hulett” and participate in an occasional “heelkicking” at his studio.

On Christmas Day, Webster set off for Philadelphia. He first saw Franklin on the twenty-eighth, and two days later, they dined together. During Webster’s ten months in Philadelphia, Franklin would regularly take time out of his busy schedule to meet with him. “The doctor,” Webster proudly recalled later, “treated N.W. with much politeness.” Though their friendship blossomed—Webster would on occasion accompany “the ladies” to Dr. Franklin’s Market Street house—their proposed literary collaboration foundered. Webster soon realized that he didn’t see eye to eye with the Doctor, who remained wedded to his old ideas about spelling reform. Speaking in his famous aphoristic style, Franklin told Webster that “those people spell best who do not know how to spell.” What the Doctor meant was that the formal rules of spelling are arbitrary, and that a purely phonetic system would make it easier for most people to read and write. Back in 1768, Franklin had drafted a treatise, A Scheme for a New Alphabet and a Reformed Mode of Spelling, in which he proposed substituting the letters—c, j, q, w, x, and y—for six new ones of his own making. The seasoned publisher had also come up with types for printing his new characters. After careful consideration, Webster politely informed Franklin that he wasn’t willing to dust off his types in order to create a new alphabet. Reflecting back on this parting of the ways in his memoir, he wrote, “N.W. . . . was then . . . of the opinion that any scheme for introduction of a new alphabet or new characters is and will be impracticable.” That account, however, doesn’t quite jibe with the facts, for as late as February 23, 1787, Webster was still lecturing about “reforming the English alphabet.” A perpetual self-promoter, Webster would not shy away from rewriting history when it suited his purposes.

While sometime during the spring of 1787, Webster lost interest in tinkering with the alphabet, he remained committed to spelling reform. In 1790, he would make the case for a new phonetic system relying on existing letters in a volume entitled A Collection of Essays and Fugitiv Writings. Webster’s proposals involved, for example, eliminating silent letters such as the “e” in “fugitive” and changing “is” to “iz.” Webster took his characteristic strong stand, arguing that “if a gradual reform should not be made in our language, it will proov that we are less under the influence of reezon than our ancestors.” But critics found his scheme incoherent, if not absurd. Jeremy Belknap, the Boston pastor who founded the Massachusetts Historical Society, quipped that he objected to “the new mode of spelling recommended and exemplified in the fugitiv Essays ov No-ur Webster eskwier junier, critick and coxcomb general of the United States.” In response to such attacks, Webster soon gave up his ambitious plan to revamp the spelling of American English. However, he would never stop pressing for less sweeping changes.

Once Webster settled in at Mrs. Ford’s rooming house on Walnut Street in early January 1787, he had to figure out how to stay afloat financially. He first tried going back to the lectern. On January 3, he met with James Sproat, the pastor at the Second Presbyterian Church at Third and Arch. Sproat was also a trustee at the University of the State of Pennsylvania, and he helped Webster gain access to a room at the university. On January 6, Webster announced in The Pennsylvania Packet and Daily Advertiser that he would be giving a series of seven lectures on language, education and government. But subscription sales were anemic. With the Federal Convention slated to come to town in May, Webster’s call for national unity, which had generated so much excitement over the past two years, was now old news. Scaling back his plans, he decided to give just two lectures.

But the public was no longer interested in even a small dose of Webster the celebrity speaker. And Webster’s social obtuseness compounded the problem. On Tuesday, January 20, the day scheduled for his first lecture, he posted an announcement in The Pennsylvania Herald and General Advertiser, in which he further alienated his potential audience by defining it very narrowly: “The public are most respectfully informed that this and another lecture are . . . not designed for amusement. . . . They are . . . for people who have leisure and inclination to devote an hour to seriousstudy.” At the same time, Webster made a feeble attempt to extend his appeal beyond just “thinking men of every denomination,” adding, “The first [lecture] is particularly calculated for ladies of sentiment, who are very influential in manners.” But his remarks on how fashion had thwarted the purposes of the Revolution didn’t endear him to anyone: “This same dress which adorns a miss of fifteen will be frightful on a venerable lady of 70. . . . But the passive disposition of Americans of receiving every mode that is offered them sometimes reduces all ages, shapes and complexions to a level. . . . So long therefore as we look abroad for models, our taste must be entirely subject to the caprice and interest of other nations.” Little did Webster realize that Americans were unlikely to embrace his call for independence in sartorial matters.

On the evening of January 20, a hard rain pelted Philadelphia, and with few people showing up, Webster abruptly canceled his first lecture. He tried again a week later, and though the weather was better, he nevertheless drew a small audience. An item in The New Hampshire Spy dated January 31—probably written by Webster himself—captured his frustration: “A [Philadelphia] correspondent laments the depraved taste of a number of his fellow citizens, in their neglect of the course of lectures, now delivering by Mr. Webster, from which a useful portion of both instruction and improvement might be derived—whilst the pantomimes . . . appear to be sanctioned by crowded audiences.” As Webster would later note in his dictionary, pantomimes (such as “Harlequin in the Moon” playing that month at Philadelphia’s South Street Theater) then referred to “a species of musical entertainment.” That he was losing potential customers to stage actors—whom he despised—was particularly galling. On February 6, before another disappointing turnout, he recycled the idea from his Connecticut editorial about the pressing need to reduce the number of lawyers. His lecturing days were about over.

Webster was feeling not only angry but bored. Not sure what to do with himself, he whiled away the hours playing whist. The frequent attacks on his integrity in the local press infuriated him still further. In early February, alluding to Webster’s “insufferable arrogance,” an anonymous writer calling himself “Juvenis” also challenged his business model: “I wish Mr. Webster would publish his observations; . . . I among others cannot afford half a dollar every evening to hear his lectures.” On February 17, Webster got into a brawl with a businessman named Mr. Blanchard, in which a chair was broken. Embarrassed by his lack of emotional control, he conceded in his diary, “Folly in little boys is excuse-able, but in great boys, it is odious.”

In April, a rattled Webster returned to his former line of work, taking a position as an English instructor at the Episcopal Church’s Academy for Boys. (The school, founded in 1785, still stands, though it has been transplanted to Devon, a suburb of Philadelphia.) But he was further humiliated when a disgruntled former teacher at the school, identifying himself only as “Seth” in The Freeman’s Journal, publicized just how far he had fallen: “This learned man . . . is now obliged to accept of two hundred pounds a year of paper money, what at present, allowing for a discount, is scarcely one hundred pounds sterling.” Never one to shy away from a verbal smackdown, Webster took to his own defense. Using the alter ego “Adam”—Seth’s father in the Book of Genesis—Webster fired back “that the gentleman who is so degraded by his acceptance of a place in the Academy . . . has received as good an education as America can afford and improved it by a personal acquaintance with the greater part of the principal literary gentlemen in the United States.” But despite the imprimatur of the literati, Webster now had a grueling day job. On April 30, he observed, “Busy enough with the Boys of the Academy, they have been managed, or rather not managed by poor low Irish masters.” This backslide in his professional life might well have led to a crippling depression were it not for an exciting new development in his personal life.

THOUGH IT WASN’T QUITE LOVE at first sight, it took only a couple of weeks for Rebecca Greenleaf to sweep Webster off his feet. Then just twenty, the petite Bostonian with the dark complexion was a head-turner, whose “fine eyes and amiable deportment have made,” one contemporary put it, “so much havoc among the beaux.” While most schoolteachers wouldn’t have had a chance at winning her heart, Webster held out some hope. The twenty-eight-year-old was a nationally known author who was himself dashing; and persistence was his forte.

They met by accident on March 1, 1787, when Webster was escorting Miss Sally Hopkins to visit Pastor James Sproat. During the course of the evening, Webster met Duncan Ingraham, a local importer of European goods, and his family. Rebecca and her brother James were both in town to visit their older sister, Suzanna (Sukey), who had married Ingraham about a decade earlier.

Within a matter of days, Webster was turning his attention away from Miss Hopkins and toward “the agreeable Miss Greenleaf,” whom he soon began seeing a couple of times a week. Every minute he spent with “the lovely Becca” was sheer delight. On March 15, Webster had dinner with Dr. Franklin, but discussions about spelling reform suddenly were no longer at the top of his agenda. The highlight of that evening, he noted in his diary, was his visit with “Miss Greenleaf, the black-eyed beauty.”

Webster was Rebecca’s constant companion at teas and concerts until she left Philadelphia in early summer. A few days before her departure, Webster wrote her a note, in which he enclosed a lock of his hair and revealed his intentions: “Permit me to assure you that your esteem—your friendship is now my only happiness and your happiness the great object of my pursuit. And if I am permitted to indulge a hope of mutual attachment, your inclinations will always be consulted in my future determinations. . . . You must go, and I must be separated from all that is dear to me.”

For the first time in his life, Webster was madly in love. He would pursue this object of his affection with the same intensity that he would pour into defeating his political and literary opponents. But with Rebecca, the combative Webster would lay down his arms. Taking on a new persona, he did his utmost to be pleasing and agreeable. “Among other instances of my readiness to obey your wishes,” he wrote while courting her, “you may rank the mode of dressing my hair. I have turned it back, and I think I look like a witch. . . . You know I do not dispute against the taste of ladies.”

By the summer of 1787, the couple had reached “an understanding” that they would eventually be married. On June 20, 1787, as Rebecca was about to go back to New England, with tears streaming down his cheeks, Webster wrote her, “Without you the world is all alike to me; and with you any part will be agreeable.” While Rebecca returned Webster’s affection, she insisted on delaying the wedding because of his lack of a steady income. The disappointed Webster raised no objections. Though he would continue to socialize with other women, including “the pretty Miss Hopkins,” he couldn’t stop thinking about his fiancée. As he wrote to Rebecca once she was back in Boston, “I sometimes go to dances and other parties, where I see ladies and good girls, too, they are. But there is not a Becca Greenleaf among them; no such tenderness, such delicacy, such sentiment and unaffected goodness.”

Rebecca’s appeal went beyond her beauty and kind disposition. Webster was also entranced by the rest of the Greenleafs (derived from the French, “Feuillevert”), a distinguished Huguenot family whose roots in Massachusetts dated back to 1635. As Webster would later advise his daughter Eliza, “When you marry, look out for the stock.” Rebecca was the thirteenth of fifteen children of William Greenleaf and Mary Brown, whose ancestor, John Browne, had been a magistrate of Plymouth Colony (and in 1654 had met Webster’s forefather, John Webster, at a gathering of key Colonial leaders). Impressed by the Greenleafs’ genealogy, that summer Webster first developed what would be a lifelong interest in his own family heritage. Initially he hoped his father might supply some answers, but he soon learned that he would have to do his own digging. “As to the history of our family,” Noah Webster, Sr., wrote from Hartford on July 28, 1787, “I have made some inquiry of old people, but cannot be very particular. . . . my desire is you may rise superiour in whatever is excellent and praiseworthy to your ancestors.”

Rebecca’s father, William Greenleaf, possessed the worldly sophistication that Webster’s own father sorely lacked. A tall, slim man, fond of his single-breasted coat and gold cane, Greenleaf was a successful Boston merchant who could easily afford to send his sons to Harvard. An avid Whig, Greenleaf was appointed sheriff of Suffolk by the Colonial governor of Massachusetts on October 31, 1775. The following year, he was at the center of a seminal moment in American history. On July 18, 1776, it fell to Greenleaf to read the Declaration of Independence from the balcony of the old State House on State Street (then called King Street) to the swirling throng below. (But the mild-mannered Greenleaf was soft-spoken, and upon hearing the insistent cries of “Read louder!,” he gave way to Colonel Thomas Crafts, another county sheriff who happened to have a booming voice.) During the war, the British ransacked Greenleaf’s elegant Hanover Street home, and the family eventually resettled in Dorchester. As children, Rebecca and her sisters all felt close to their kind-hearted father, whom they would shower with kisses upon his comings and goings. An endless supply of paternal affection would transform the Greenleaf girls into easygoing and devoted wives.

By contrast, Rebecca was wary of her mother, described by family members as “cold” and “haughty.” Mary Greenleaf banished several of her infant children to the country, where they were cared for by a wet nurse until they reached three or four. Rebecca’s stern mother was the parent to whom Webster would have to prove his dependability as a breadwinner.

Webster was intrigued by the prospect of having so many prominent new relatives. In Philadelphia that summer, he cemented his ties with both the wealthy and savvy Duncan Ingraham and with Rebecca’s brother James, then an up-and-coming speculator. Webster would soon become close to the Boston lawyer Thomas Dawes, who had married Rebecca’s sister Peggy, and Dr. Nathaniel Appleton, also of Boston, the husband of her sister Sarah. Over the next couple of years, Webster would enlist the help of several members of the extended Greenleaf family in solidifying his finances.

William and Mary Greenleaf, who left behind some eighty-nine grandchildren, would spawn a bevy of distinguished descendants. Their fifteenth child, Nancy, would marry William Cranch—who as a schoolboy, accompanied by his cousin John Quincy Adams, had seen Greenleaf on the balcony of the State House that July afternoon in 1776. Cranch, who became close to Webster, later served as a chief judge of the circuit court of the District of Columbia. One of the Cranches’ thirteen children, Abigail Adams Cranch, married William Greenleaf Eliot, the Unitarian clergyman who founded Washington University in St. Louis; among the grandchildren of William and Abigail Eliot was the St. Louis-born Nobel laureate, the poet T. S. Eliot.

ON WEDNESDAY, AUGUST 22, 1787, Webster marched over to the banks of the Schuylkill River to see if the strange invention could, in fact, “walk the waters like a thing of life.”

The invention was the steamboat, and its inventor was a tall, thin man with jet black hair and a fiery temper named John Fitch. In the forty-four-year-old Fitch, whom he had first met that winter, Webster found a kindred spirit. A farmboy from Windsor, Connecticut, seven and a half miles north of Hartford, Fitch had stopped attending school not long after his fifth birthday. But Fitch was “nearly crazey after learning” and despite a lack of support from his father, he devoured books such as Thomas Salmon’s Geographical and Astronomical Grammar in the hope of gathering “information of the whole world.” Apprenticed to a clock-maker, Fitch had worked as a brass founder, clock mender and surveyor until 1785 when he could no longer think of anything else but “propelling a conveyance without keeping a horse.”

As Webster well understood, inventors faced some of the same challenges as authors. Like Webster, Fitch had recently mounted a copyright campaign to protect the fruits of his labor. By that summer, Pennsylvania, Delaware and New York had passed special laws (analogous to those Webster had requested for his speller) under which Fitch retained exclusive rights to his invention for a period of fourteen years. To gather recommendations from the biggest names in America, Fitch had set up this experimental trial for the “Convention Men.” He first invited William Samuel Johnson, a Connecticut delegate, who agreed to ride with him in the boat. And Dr. Johnson—the 1744 Yale graduate and future president of Columbia had received an honorary doctorate from Oxford—had alerted the rest of the delegates. While Webster and a couple of dozen “Convention Men” watched from the shore, about twenty others were on deck for the test run. That afternoon, Fitch’s experiment actually took precedence over the nation’s business as the delegates adjourned the convention early. “There was very few,” Fitch later wrote in his autobiography, “of the convention but called to see it.”

Throughout that summer, Webster was spending a lot of time with “Convention Men,” particularly those with Connecticut ties. On Independence Day, he had called on Dr. Johnson, as well as on Abraham Baldwin, a Yale tutor during his undergraduate days, who was representing Georgia. In early August, Webster spent an evening with Connecticut’s two other delegates, Oliver Ellsworth, his former boss, and Roger Sherman; a few weeks earlier, the pair had fashioned the “Connecticut Compromise,” which set up America’s dual system of representation in its two houses of Congress. And Webster also socialized with the Virginia delegates, James Madison and John Marshall, at whose house he would spend the evening of August 23.

Some forty-five feet long, the boat was powered by a 12-inch cylinder that sat above a small furnace. A crank over the stern propelled the half-dozen paddles, resembling snow shovels, that lined each side. Though it went just two and a half miles an hour, the vessel completed its journey from the Delaware River to Gray’s Ferry in the Schuylkill River without a hitch.

Webster, like the delegates, was impressed. Their unanimous verdict was summed up in a note passed on to the inventor by a servant the following day that began, “Dr. Johnson presents his compliments to Mr. Fitch and assures him that the exhibition yesterday gave the gentlemen present much satisfaction.” All of Connecticut would soon be immensely proud of this stunning feat by its ingenious native son. When meeting Ezra Stiles a few days later in New Haven, a beaming Ellsworth, who hailed from Fitch’s hometown of Windsor, was as eager to share this exciting news as he was to report on the progress of the convention.

Though the experiment was an unqualified success, Fitch still had lots more work to do. He needed to build a bigger motor and increase the speed. In 1791, he obtained the first federal patent for a steamboat, but he never could raise the funds to proceed any further. Fitch’s talents were as an inventor, not a venture capitalist. He soon lapsed into drink and despair, exclaiming, “The day will come when some more powerful man will get fame and riches from MY invention; but nobody will believe that poor John Fitch can do anything worthy of attention.” In 1798, he downed a dozen opium pills and died in his sleep. True to Fitch’s prophecy, in 1807, Robert Fulton, who had been working as a miniature portrait painter in Philadelphia during the Constitutional Convention, would emerge as “the father of the steamboat” and reap all the financial benefits.

Webster would forever be obsessed with Fitch. A half century later, he wrote to a friend, “A biography of John Fitch is a desideratum yet to be supplied.” And in 1842, upon hearing that the writer Eliza Leslie was getting ready to publish her life of the inventor, Webster wrote a long letter to Graham’s Magazine, the Philadelphia literary journal then edited by a budding writer named Edgar Allan Poe, in which he recalled his first visit aboard Fitch’s boat in February 1787. Of Fitch, Webster also noted, “His . . . papers . . . were . . . found to contain a minute account of his perplexities and disappointments. The memoir of such a man . . . cannot help but present the deepest interest.” Reflecting back on his own successful literary career, Webster felt that he had narrowly escaped Fitch’s tragic fate.

ON MONDAY, SEPTEMBER 17, 1787, in the capacious east room of the Pennsylvania State House on Fifth and Chestnut, which Webster considered “magnificent rather than elegant,” the final draft of the Constitution was read aloud. Before the vote, Benjamin Franklin handed Pennsylvania delegate James Wilson a few remarks that he had prepared for the occasion. Reading from Franklin’s notes, Wilson stated, “On the whole I can not help expressing a wish that every member of the Convention who may still have objections to it . . . doubt a little of his own infallibility, and to make manifest our unanimity, put his name to the instrument.” Franklin’s insistence on the pressing need to approve an imperfect document carried the day. Late that afternoon, the Great Convention adjourned. That night, the members dined together for the last time at the City Tavern. Before going to bed, George Washington, who would leave town the next day, wrote in his diary that he “[meditated] on the momentous work which had been executed, after not less than five, and for a large part of the time six and sometimes 7 hours sitting every day . . . for more than four months.”

On Tuesday the eighteenth, Webster was in the Pennsylvania State House as President Franklin presented the Speaker of the House of Assembly—Thomas Mifflin—with the plan of the new federal government. Bells then rang throughout the city. Though Americans could now celebrate that a steamy summer of wrangling had resulted in a founding document, another round of fierce debate remained. Before it could become the law of the land, nine states would have to vote for ratification. Recording the historic events that night, Webster noted, “All America waits anxiously for the Plan of Government.”

But Webster would be no mere bystander. He would immediately get back to work on behalf of the national unity that he had long desired. And his country urgently needed his pen. On September 15, Thomas Fitzsimmons, a Pennsylvania delegate, had sent a personal note seeking his assistance: “It is already too evident that there are people prepared to oppose it [the Constitution]. . . . From a conviction that your abilities may be eminently useful on the present occasion, I am induced to call your attention to the subject. If as a friend to your country, you can support the act of the convention, I hope you will exert yourself to that purpose.” The savvy publicist jumped at the chance to extol what Washington, Franklin, Madison and Hamilton had wrought. Barricading himself in his room for two full days in early October, Webster completed a pamphlet, “An Examination into the Leading Principles of the New Federal Constitution Proposed by the Late Convention Held at Philadelphia,” which he dedicated to “his Excellency Benjamin Franklin, Esq.” Having been recently vilified in the popular press, Webster signed it “A Citizen of America.” This pen name, he felt, was likely to improve his chances of getting a fair hearing.

Published as soon as the ink was dry and excerpted in The New Hampshire Gazette later that fall, Webster’s essay took Franklin’s core argument directly to the American people: “It is absurd for a man to oppose the adoption of the constitution, because he thinks some part of it defective or exceptionable. . . . Perfection is not the lot of humanity.” In simple language, Webster explained how America’s founding document stacked up against its predecessors created by rulers such as Confucius, Moses and Peter the Great, describing it as “an improvement on the best constitutions the world ever saw.” He also emphasized the danger of a reversion to Hobbesian chaos should it not be ratified: “The present situation of our states is very little better than a state of nature.”

Though aware of the Constitution’s shortcomings, Webster didn’t stint in his praise. The future lexicographer found the work of the “Convention Men” eminently clear: “The constitution defines the powers of Congress; and every power not expressly delegated to that body, remains in the several state legislatures. The sovereignty and the republican form of government of each state is guaranteed by the constitution; and the bounds of jurisdiction between the federal and state Governments are marked with precision.” His hastily conceived tract, Webster later acknowledged in his memoir, lacked the theoretical sophistication of the Federalist Papers, the series of eighty-five newspaper articles defending the Constitution, which began appearing a couple of weeks later in New York newspapers. As an admiring Webster would put it in 1788, these seminal writings of Hamilton, Jay and Madison passed muster for the same reason as the Constitution itself: “It would be difficult to find a treatise . . . in which the true principles of republican government are unfolded with such precision.” Though the Federalist Papers are much better known to history, at the time Webster’s pamphlet may well have exerted even more influence, particularly outside New York State. That November, South Carolina’s David Ramsay thanked Webster for sending his “ingenious pamphlet,” adding that “it is now in brisk circulation among my friends. . . . It will doubtless be of singular significance in recommending the adoption of the new Constitution.”

ON OCTOBER 16, 1787, the day before his remarks on the Constitution were published, Webster celebrated his twenty-ninth birthday. “I have been industrious—endeavored to do some good,” he confided to his diary, “and hope I shall be able to correct my faults and yet do more good. Put my trunk abroad for New York.” His self-esteem was in tatters because, once again, his financial future was up in the air. Two weeks earlier, he had resigned from the Episcopal Academy, and his only source of income was now the trifling three hundred pounds in royalties that he could expect from his books. No longer having any business in Philadelphia, he began making preparations to head north. But where would he go and what would he do to earn the money he needed to be reunited with his beloved Becca?

At the suggestion of Franklin, with whom he spent a couple of evenings before leaving Philadelphia at the end of October, Webster decided to start a new literary magazine. Though the new nation’s overall economy was still fragile, this sliver of the publishing industry was booming. Between 1776 and 1800, some forty new magazines would crop up in America, nearly two and a half times as many as had appeared in all the years prior to the Revolution. The reigning king of the genre was Philadelphia’s Columbian Magazine or Monthly Miscellany, edited by Matthew Carey, which had been modeled on Britain’s Gentleman’s Magazine. With Carey also launching a similar publication, The American Museum, in 1787, Webster set his sights on America’s second city. As he explained to Benjamin Rush, “The place I have chosen for publishing it is not the seat of literature, but . . . to begin another [in Philadelphia] would be neither generous nor eligible. New York will always be the destination of the packets, and the facility of the intercourse with all parts of America gives it a preference which can never be rivaled.” To highlight his continuing interest in shaping his country’s identity, Webster resuscitated a title—The American Magazine—that had graced the covers of a half-dozen short-lived Colonial periodicals.

After spending a few weeks in Hartford and New Haven visiting family and friends, Webster relocated to New York City on November 29. The following week, he announced his new publication in The New York Packet: “This work will . . . will consist principally of original essays in prose and verse upon a variety of subjects. . . . The editor . . . has ever been fond of books, and has leisure to devote most of his time to a publication which, if well conducted, will contribute to the amusement and improvement of his enlightened countrymen.” Having learned a lesson from the lukewarm response to his last round of lectures, which were not designed for “amusement,” Webster would try, despite himself, to add a touch of levity. In his ad, Webster also solicited contributions from “men of genius.”

But with few writers responding to his query, Webster would have to scramble for copy. In the first issue, dated December 1, 1787, but published a month later—at the time, it was common for magazines to appear after the issue date rather than before—he recycled the work of old Yale friends, inserting an excerpt from the Trumbull poem, “The Rare Adventures of Tom Brainless,” the first part of “The Progress of Dulness,” and the first half of Dwight’s valedictory address from July 25, 1776. He would save further installments of both works for future issues. Likewise, Webster reprinted literary efforts by his British heroes, such as “The Fountains,” a fairy tale by the recently deceased Samuel Johnson. He also featured the first of what would be fourteen original essays on education, in which he reiterated his pet peeve that American schools had neglected the study of the English language, noting that “the high estimation in which the dead languages have been held, has discouraged a due attention to our own.” Finally, that inaugural issue included an editorial on the Bill of Rights, which Webster called “absurd.” The reason: “no constitutions in a free government can be unalterable.”

To fill up those sixty-four octavo pages each month, Webster also composed numerous lighthearted pieces, which he published under pseudonyms. Writing at a feverish clip, he didn’t hesitate to put his own internal preoccupations to paper. Picking up a thread from his nearly empty Philadelphia lectures, “Titus Blunt” railed against the long tails of ladies’ gowns as an example of “fashion that besides its inconvenience and the expense it incurs can hardly be reconciled with neatness.” Both “Philander” and “Guy Grumbleton” touched on Webster’s own anxiety about his upcoming marriage, with the former stating that “all objections to matrimony, arising from an apprehension of the expense, will be removed as soon as a man is heartily in love” and the latter, an unhappy newlywed, carping that “either I was blind or the lady was deceitful.” Likewise, in a satiric essay entitled “The Art of Pushing into Business and Making Way in the World” (an eighteenth-century version of How to Succeed in Business Without Really Trying), “Peter Pickpenny” gave voice to Webster’s frustrations with his chosen vocations. Of law, he quipped, “the success (or profit, which is the same thing) of the profession depends much on a free use of words, and a man’s sense is measured by the number of unintelligible terms he employs.” His advice: “remember that the pence are multiplied with the words in the writing.” “Pickpenny” also revealed the magic formula that sparked the staggering sales of Webster’s own speller: “the first thing to be attended to is to prepare a blustering advertisement, recommending the work before it appears. People are caught with promises that a work shall be the best that ever was seen altho no one expects it; and who more fit to recommend a publication than the author or compiler?” Webster also turned advice columnist and amateur psychologist. Besieged by those same sexual fantasies that Webster had heretofore confined to his diary, an anxious “Curio-sus” wrote to the editor: “I was at a ball a few evenings ago, and my eyes, wandering over a circle of beautiful young ladies, fixed upon a Miss—to whom I am a stranger. Her regular features—fine complexion—persuasive eyes—coral lips—graceful deportment and I know not what attractions, charmed me into admiration and made me commit twenty blunders in dancing.” Webster’s recommended course of action was simple: “become acquainted with the charming girl.” Of Webster’s multiple aliases, Ebenezer Hazard, a fellow New York publisher, observed that spring, “NW goes on publishing letters to himself.”

Webster’s attempts to be entertaining didn’t grab too many readers. With sales of the first two issues slow, Webster began flirting with another novel idea, driven by his two major obsessions: American unity and statistics. According to a plan he hatched in early February, ten correspondents scattered across the country would funnel him mountains of descriptive data about America. As he explained to Benjamin Rush, whom he hoped to enlist as his Philadelphia reporter, “I have begun . . . a magazine in this city; but I wish to extend the publication and comprehend all the original and valuable matter in the United States and communicate it to the whole. The business of the proprietors should be to collect [materials on] . . . the state of government, finance, commerce, manufacturers, populations, sciences and every species of arithmetic information and communicate it to the editor.” As proprietors, his colleagues would also share in the magazine’s profits. Webster was convinced that this “useful intelligence” would both result in a sixfold increase in circulation—then stuck at about five hundred copies a month—and “gradually cement our union.” Besides Rush, Webster also reached out to his Yale friends Barlow, Trumbull and Dwight in Connecticut, as well as James Madison in Virginia, and Jeremy Belknap, whom he barely knew, in Boston.

Unfortunately, this new direction for the magazine didn’t make sense to anyone but Webster. Typical was the reaction of Belknap, who took four months to write back. Unsure what to make of Webster’s interest in “returns of deaths, burials &c., entries at custom-houses, philosophical observations on the weather, the degrees of heat & cold, celestial phenomena, state of civil and ecclesiastical polity, colleges, ancient records & curious anecdotes, &c &c,” Belknap decided to consult with his friend Ebenezer Hazard, then America’s postmaster general. Though Belknap already had some reservations about Webster the man, whom he nicknamed “the Monarch,” he wanted an insider’s assessment of the business plan. Hazard recommended that Belknap steer clear of Webster: “I think the Monarch a literary puppy, from what little I have seen of him. He certainly does not want understanding, and yet there is a mixture of self-sufficiency, all-sufficiency and at the same time a degree of insufficiency about him, which is (to me) intolerable.” Summing up, Hazard quipped, “The Monarch (I think) ought to reign alone.” By late June, when Belknap politely declined Webster’s offer, Webster’s scheme was already dead. But Webster did manage to sprinkle some data in his pages, which also included his famous description of New York as well as a similar piece about Philadelphia. And without any correspondents supplying him with statistics from New England, he gathered a few from England himself. In the April 1788 issue, he devoted a page to “The London General Bill of Christenings and Burials From Dec 12, 1786 to December 11, 1787.” After noting that 8,929 males and 8,579 females were christened and 9,821 males and 9,528 females were buried during this period, he reprinted the causes of all these deaths—a three-column list of diseases followed by a one-column list of casualties (accidents). Under the former were such entries as “Grief, 1” “Headach, 1”; under the latter was a particularly curious entry, “Bit by a mad dog, 0.”

The statistical impulses run amok reflected Webster’s sadness and loneliness. The months he had spent with Rebecca the previous spring had given him a taste of a whole new way of being in the world, which he sorely missed. As he wrote to her in February, “I sometimes enjoy your company in dreams; a few nights past, I was with you and passt a few happy hours with your smiles and your conversation. Would to heaven every night might be so happy.” With Rebecca back in Boston, his courtship had to take place exclusively through the mail. In New York, he did, however, see a lot of her brother James, whom he soon considered a trusted friend. And James Greenleaf was, in turn, grateful to Webster for introducing him to his new business partner, James Watson. The prospect of a future with the Greenleafs kept him from disintegrating. In early 1788, he wrote Rebecca: “You will see by the tenor of this letter that I am in the dumps a little. . . . Well, I wish everybody were as good as James Greenleaf and his sister, Becca. I should then be a much happier man, but as it is, I shall not be unhappy. I am as patient as possible waiting for the sun to disperse the clouds that hang over the head of your cordial friend and admirer.” But the wait to marry his beloved Becca would repeatedly try his patience. Over the next year and a half, an overworked and anxious Webster would come close to a nervous breakdown. In the words of Ebenezer Hazard, he was as “unstable as water.” And as his magazine faltered, Webster was prepared to do whatever it took to marry Rebecca—even renounce all his literary activities. Summing up his first three decades in 1788, Webster confided to his diary, “I have read much, written much. . . . I will now leave writing & do more lucrative business. . . . But I am a bachelor and want the happiness of a friend whose interest and feelings should be mine.”

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