Marriage and a Turn Away from Words

MARRIAGE, n. The act of uniting a man and woman for life; wedlock; the legal union of a man and woman for life. Marriage is a contract both civil and religious, by which the parties engage to live together in mutual affection and fidelity, till death shall separate them. Marriage was instituted by God himself for the purpose of preventing the promiscuous intercourse of the sexes, for promoting domestic felicity, and for securing the maintenance and education of children.

In the summer of 1788, as Webster worried about whether his marriage with Rebecca Greenleaf would ever take place, there was another union that he could celebrate. On June 25, New Hampshire became the ninth state to ratify the Constitution. Webster’s dream of a Federalist United States of America was now a reality. That night, he wrote in his diary, “Great joy at the ninth.”

Webster had just returned to New York City after attending the opening of the New York State ratifying convention in its capital, Poughkeepsie. While upstate, he took a brief excursion to see Cohoes Falls, the waterfall on the Mohawk River, where he couldn’t resist doing a little quantifying. “I measure,” he recorded in his diary, “the banks of the river, 100 feet, the falls more than half that distance.” By the time he left Poughkeepsie on June 20, the anti-Federalists, led by Governor George Clinton of Albany, still outnumbered the Federalists—mostly based in the city—by a margin of more than two to one.

To mark the ratification of the Constitution, New York had hoped to join other cities such as Philadelphia and New Haven that were scheduling parades for July Fourth. But with the state convention still deadlocked, the city put its plans on hold. After a series of postponements, the Revolutionary War hero Colonel Richard Platt, the chairman of the Committee of Arrangements for the New York Procession, settled on Wednesday, July 23. This majestic display of support for America’s founding document, Platt figured, could perhaps sway the votes of some upstate delegates.

A fierce advocate of national unity and an arranger extraordinaire, Noah Webster, Jr., quickly became Platt’s right-hand man. On July 17, Webster wrote in his diary, “Meet the Committee of Arrangement . . . and order the procession for the 23rd.” In the end, Webster would not only organize the parade, he would also become its chief chronicler. Generations of historians have turned to the definitive account, which he “arranged for the public,” published under Richard Platt’s byline in New York’s leading paper, The Daily Advertiser. Four decades later, to illustrate the verb “witness” in his dictionary, Webster would note, “I witnessed the ceremonies in New York, with which the ratification of the constitution was celebrated, in 1788.” But this statement downplays the full extent of his involvement.

Platt recruited Webster because he was the driving force behind the New York Philological Society, an influential coterie of literary scholars, which would be one of roughly seventy trade associations marching in the parade. Besides Webster, who was officially its secretary, this group included the lawyer Josiah Hoffmann, its titular president; the play-wright William Dunlap, its treasurer; and the naturalist Samuel Latham Mitchill, then a newly minted doctor. (A future congressman, Mitchill, who shared Webster’s obsession with classifying and arranging, was later nicknamed “the Congressional Dictionary” by Thomas Jefferson.) In April, Webster had written the Philological Society’s constitution; dedicated “to the investigation upon which language is founded,” the organization aimed “to ascertain and improve the American tongue.” And to achieve this goal, as Webster confided to publisher Isaiah Thomas in June, the society initially planned to produce a dictionary. Though this massive undertaking never got underway, that spring Webster gave a series of lectures during the group’s Monday night meetings in which he put his stamp on all its activities. As Ebenezer Hazard observed, “I do not know all the members of the Philological Society, though I have understood that they are not numerous. The Monarch reigns supreme . . . [over] . . . his subjects.”

However, Webster’s decision to shepherd the Philological Society wasn’t motivated purely by patriotism. He was also looking for more publicity for his speller. On July Fourth, President Hoffmann wrote an endorsement on behalf of the society, in which he stated that Webster’s book was “calculated to destroy the various false dialects in the several states . . . an object very desirable in a federal republic.” By establishing the norms of a new federal language, the group could also, so Webster hoped, give his textbooks a virtual monopoly in the nation’s school systems. That summer, he wrote to his publisher: “When you advertise the improved editions of the Institute, something like the following may be published. . . . The Philological Society in New York recommend this work with a view to make it the federal school book. The University of Georgia, preferring this to Dilworth . . . or any other . . . have determined that this alone shall be used in all the schools in that state. The publishers flatter themselves that the northern states will heartily concur in the design of a federal language.

Webster thus was counting on the Philological Society to help him cash in on the passage of the Constitution, which suddenly improved the commercial prospects for his books.

For the nearly thirty-year-old Webster, the New York procession represented the triumph of everything he stood for—patriotism, national unity and order. He felt a sudden surge of optimism, noting in his August piece in The Daily Advertiser, “the great object of exultation . . . was . . . an era in the liberty of man, great glorious and unparalleled, which opens a variety of new sources of happiness and unbounded prospects of national prosperity.” In a life filled with anxiety and toil, it would be a rare day of pure exhilaration, which he would share with the rest of a thoroughly delirious and united Manhattan Island.

ON THE MORNING OF JULY 23, Webster, dressed in the black uniform of the Philological Society, left his Maiden Lane residence and walked up to the area then known as “the Fields” (today City Hall Park). He soon joined a throng of some five thousand working men, who had been gathering since eight o’clock. Thousands more started lining up on the spotless streets along the parade route, which had been swept and watered both earlier that morning and the night before. The city’s ladies, preferring to avoid the crowds, stationed themselves in doorways and at windowsills.

Just as red, white and blue were the procession’s predominant colors, ten and thirteen were its operative numbers. That’s because at the beginning of July, Virginia had become the tenth of the thirteen states to approve ratification.

At exactly ten o’clock, thirteen guns from the federal ship Hamilton, built especially for the occasion, announced that the procession was to begin. Horsemen with trumpets started down Broadway, along with a company of artillery. Then came Grand Marshal Richard Platt, dressed in a blue coat, red sash and white feather, followed by his thirteen deputy marshals.

Finally, the ten divisions of artisans fell into line, each one led by a man carrying a white banner. The workers, forming a mile-and-a-half retinue, came from all walks of life. In this day of unity, the young, the old, the rich, the poor, the learned and the uneducated were all marching as one.

The first division consisted largely of artisans whose work had something to do with the land or its by-products: farmers, foresters, gardeners, millers, distillers and bakers. As the new United States of America was largely an agrarian nation, this contingent was the longest, containing fourteen subdivisions. Wit and ingenuity were everywhere on display. The bakers featured four masters who carried a ten-foot-long “federal loaf” upon which was emblazoned the names of the ten ratifying states and the initials of the three holdouts: N.Y., N.C. and R.I.

Coopers (makers and repairers of wooden barrels) led the second division. As Webster would later describe their arithmetically appropriate tribute: “Thirteen apprentice boys, 13 years of age, dressed in white shirts, trowsers, and stockings. . . . their hats ornamented with 13 pillars, colored green and white, with ten branches springing from them.”

A few hundred yards in front of Webster paraded the chocolate makers, who were grouped with the blacksmiths and instrument makers in the eighth division. Their float captured graphically what he had been writing about for the past half-dozen years. To represent the powerless Congress under the Articles of Confederation, they carried a picture of a naked man, whose thirteen heads were all looking in different directions, upon which was written:

When each head thus directing, 

The body naught pursues; 

But when in one uniting 

Then energy ensues.

Led by Webster, the Philological Society, subdivision 69, marched right behind the “Gentlemen of the Bar” who headed the ninth division. This contingent of the city’s intelligentsia also featured subdivisions 70 and 71: students and professors from Columbia, including the college’s president, William Samuel Johnson, as well as traders and merchants.

Webster carried a scroll containing the principles of a federal language. Behind him walked President Josiah Hoffmann in a sash of blue and white ribbons, and Treasurer William Dunlap carrying the society’s highly intricate coat of arms, which Webster had helped to design two weeks earlier. Its major elements included three tongues, a chevron and an eye over a monument sculpted with Gothic, Hebrew and Greek letters. Its crest, whose symbolism no doubt was understood only by its creators, consisted of a cluster of cohering magnets attracted by a large key, meant to highlight that language was a unifying principle of knowledge. The flag was embellished with the phrase “the Genius of America” and crowned with a wreath of thirteen plumes, ten of them starred. While her right hand pointed to the Philological Society, in her left was a pendant with the word “CONSTITUTION.”

After reaching the bottom of Broadway, the procession looped around and headed back north via Queen and Arundel streets. Webster was energized by occasionally glancing over at the ladies, those “fair daughters of Columbia whose animated smiles and satisfaction,” he would later write, “contributed not a little to complete the general joy.” There was no music and the solemnity of the event precluded cheering: “No noise was heard but the deep rumbling of carriage wheels, with the necessary salutes and signals. A glad serenity enlivened every countenance.”

As the marchers arrived at City Alderman Nicholas Bayard’s farm, which bordered on the upper reaches of Broadway, they were reviewed by Grand Marshal Richard Platt before dispersing. Leaving their signs on the fields, they headed to dining tables located in the three pavilions built by the architect Pierre L’Enfant (whom Washington would later commission to design the new federal city on the Potomac), in just five days. The banquet area, which was some 600 by 900 feet, featured ten colonnades festooned with wreaths. Under the dome of the middle pavilion—topped by the figure of Fame, carrying a parchment alluding to the three phases of the late war (Independence, Alliance with France, Peace)—sat members of Congress, foreign dignitaries and the city’s clergy.

Along with some six thousand other revelers, Webster feasted on roasted mutton and ham and imbibed abundant amounts of beer. At the end of the meal, he raised his glass to thirteen toasts—the last one being “May the union of the United States be perpetual”—each of which was marked by shots from ten cannons.

In this celebration of unity, no New Yorkers would be left out. Afterward, the same repast was passed on to all the city’s prisoners.

At five thirty, the marchers returned to their original stations and were dismissed.

That night, just as Webster was describing the procession in his diary as “very brilliant, but fatiguing,” Richard Platt wrote to the Poughkeepsie delegates that “the most remarkable regularity and decorum prevailed during the whole day.”

Platt, Webster and their fellow arrangers soon achieved their primary political objective. At nine o’clock on Saturday evening, July 26, as Webster was working away at his newspaper account of the event, he heard shouting in the streets; Poughkeepsie had rendered its final verdict. “News of the Convention’s adopting the Constitution received,” he wrote in his diary, “& great joy testified.”

ON AUGUST 2, Ebenezer Hazard wrote to the Boston pastor Jeremy Belknap, “I hear the Monarch (not of France) intends to honour this town with a visit.”

Webster was indeed heading north to see Rebecca for the first time in more than a year. On Sunday, August 10, along with Hazard and Rhode Island’s congressional delegation, he sailed to Providence. Two days later, he waited on “the dear girl” at her home in Dorchester. And on the fourteenth, he officially asked for her hand in marriage. “Ask consent of Mr. Greenleaf,” he noted in his diary, “& am happy in receiving it.” However, to reassure the Greenleafs of his suitability as a breadwinner, Webster had to promise to give up his literary career and return to law. This decision would soon become a source of constant anguish.

Once back in New York, Webster made plans to dispose of his magazine. In November, he negotiated a deal with both Hazard and another New York publisher, Francis Childs, who planned to revive it the following year under the title The American Magazine and Universal Register. Under this proposal, the magazine would be expanded to a hundred pages, and the second half of each issue would feature key documents from American history. “It has been . . . frequently lamented by the lovers of useful license that no particular account of the origin and complete establishment of this rising empire hath yet been given to the world,” ran the announcement in New York’s Daily Advertiser. Webster had hoped to print, for example, John Winthrop’s journal, which he had recently discovered at the house of former Connecticut governor Jonathan Trumbull. But nothing came of it. With circulation down to just two hundred, the magazine ceased publication after its one-year run. Rather than adding anything to his coffers, this venture had ended up costing him about two hundred and fifty pounds (five hundred dollars).

That fall, Webster’s future in-laws sent him congratulatory notes on his engagement. Writing from Amsterdam, where he had gone to pursue various business opportunities, James Greenleaf assured him, “As you have gained the consent of my parents & friends, if mine is either necessary or acceptable, you have it in the fullest manner.” Greenleaf also offered to help Webster financially, though he didn’t specify exactly how much money he could provide. In late November, Dr. Nathaniel Appleton of Boston, who had known Rebecca for a decade, observed, “If you make this girl your partner for life, you will have acquired the most amiable and all accomplished lady for a man of sentiment and taste for domestic life, which this metropolis affords. You cannot prize her too highly.” With Webster deciding to move to Boston, Appleton found him temporary lodgings: the best room at Mrs. Archibald’s, the Court Street residence where he had lived the summer before, for twenty-four pence a week. Webster was looking forward to living near all the Greenleafs.

On December 20, Webster was “happy to quit New York.” He spent Christmas with his parents in the West Division. On New Year’s Eve, Webster arrived in Boston, where he soon enjoyed frequent visits with his “agreeable new friends.” On those evenings when he wasn’t having dinner with Rebecca or other members of the extended family, he was socializing with the city’s elite. On January 28, 1789, he met the incoming vice president, John Adams, at the home of former governor James Bowdoin.

Building a legal practice, he soon realized, would take at least a few years. On February 1, in a letter to James Greenleaf, then still in Amsterdam, Webster highlighted his precarious finances: “I have done with making books. I shall enter upon the pursuit of law immediately and practise either in Hartford or this town. . . . I am as happy as the heart of the loveliest of her sex and the kindness and esteem of all your connections can make me. . . . I shall try to make it convenient to marry in the course of the year, but it depends partly on your assistance and partly on the events that are not altogether in my power.”

Two weeks later, Webster received his first letter from Greenleaf in months, in which he learned that his future brother-in-law had married a Dutch woman, Antonia von Scholten. Webster wrote back the next day, once again stressing his need for a handout: “I perceive by your letter . . . that you have engaged some provision for Becca at her marriage. This will furnish a house genteelly. . . . As a person interested in your favors to your sister, I feel grateful and number you among my benefactors as well.” As Webster also explained to Greenleaf, he now planned to move back to Hartford where he had more contacts in the legal community.

That winter in Boston, Webster superintended the publication of what he thought would be his final book, Dissertations of the English Language, the four-hundred-page tome that featured the language lectures from his two-year book tour. Published in May, it fell on deaf ears. On account of the printing costs, Webster was out four hundred dollars. His only consolation was praise from Benjamin Franklin, to whom he had dedicated it. At the close of 1789, just a few months before his death, the Doctor would write Webster a long letter about this “excellent work . . . [which] will be useful in turning the thoughts of our country men to correct writing.”

In May, Webster moved back into the Hartford residence of his longtime friend John Trumbull, where he would be paying tenpence a week. Upon his return to his hometown, his former boss Oliver Ellsworth wrote him a welcoming note from New York, where he was serving in the U.S. Senate: “I congratulate you and the city of Hartford on your settlement there in the practice of law.” Ellsworth also offered Webster the option of moving back into his home—now vacant—where he had lived a few years earlier. (Two years later, Webster and his wife would wind up there.) Webster was once again circulating among the town’s beau monde. That summer, he dined with Colonel Jeremiah Wadsworth, the influential merchant then serving in the House of Representatives; Dr. Lemuel Hopkins, the well-known poet; Nathan Perkins, the West Division pastor; as well as his Yale classmates Oliver Wolcott and Uriah Tracy.

Though he enjoyed reconnecting with his Hartford friends, Webster was feeling frustrated. His new profession was turning out to be no more lucrative than his old one. Legal work was hard to come by. And for the first time in years, he had no new literary project to fall back on. In addition, that summer, due to a hand injury, he could barely manage to keep up with his correspondence. Bored, he didn’t know what to do with himself. On June 17, he wrote in his diary, “Begin to bathe in the morning.” The following day, he added, “Repeat it with benefit.” “Ditto” was his wrap-up of the nineteenth.

In late August, Webster’s spirits revived when he heard from Greenleaf for the first time since April. “I cannot refuse,” his soon-to-be brother-in-law wrote, “to join my approbation to that of my family that your marriage may take place as soon as you think prudent.” To express his affection for the young couple, Greenleaf advanced them a thousand dollars. Webster promptly rented a comfortable house in the center of town from Colonel Wadsworth for a hundred dollars a month. Throughout the first week of September, as he recorded in his diary, he was “still employed in getting furniture.” Starting a new life with Rebecca was now his top priority. For the time being, he would do without words.


ON SATURDAY, OCTOBER 24, 1789, at about two o’clock in the afternoon, President George Washington made his entrance into Boston. Washington, who had taken the oath of office on April 30 on the steps of Federal Hall in New York City, was touring New England for the first time as president. The previous week, he had visited Hartford, where he had spent a day in the company of Webster’s social circle, meeting with both Wadsworth and Ellsworth. Upon crossing the Charles River from Cambridge, Washington was whisked to the balcony of the state house. There he was serenaded by an ode that began:

Great Washington the Hero’s come! 

Each heart exulting 

Thousands to their deliverer throng 

And shout him welcome all around!

Washington reviewed a procession of Boston’s artisans, tradesmen and manufacturers that took place on the street below. That evening, the city’s main public houses (such as the Coffee House on State Street) were illuminated, and there was also a fireworks display. The roughly twenty-five thousand spectators who saw the president behaved with “good order and regularity,” according to The Boston Gazette.

“All the world is collected to see [Washington],” Webster wrote in his diary. One of the few people then in Boston not in attendance was Webster himself; he was incapacitated by nausea.

Webster had been a nervous wreck for weeks. Financial concerns were gnawing at him. On October 12, he wrote James Greenleaf from Hartford:

The progress of young lawyers is nearly ascertained in this town. . . . [After four years, they] . . . make a little money & after that, they have generally pretty full practice. . . . I have as good a prospect as my neighbors; better I cannot expect. Still I am anxious. The dear girl who has given me her heart and who has made a sacrifice of all her natural connections for a union with me has a claim, not nearly to kindness, but to peculiar attention. She has sensibility and must be very particularly unhappy in any misfortunes that should befall us. I feel already a thousand anxieties on her behalf.

Five days later, on October 17, 1789, the day after turning thirty-one, Webster headed to Boston for his wedding. In his diary, he couldn’t quite face this fact head-on, alluding instead to “an important errand” (a word he would define in 1828 as “a mandate” or “order”). Though Webster had longed for this day for years, he was suddenly filled with dread.

Webster contracted the flu on Wednesday, October 21. For the next four days, he could barely move. On the night of Washington’s visit, he was reduced to using the third person to describe his symptoms. “The head appears,” he wrote in his diary, “to be fastened with chains, and the disorder is attended with a cough. The best remedy is hot liquors to produce perspiration. . . . But if the stomach is disordered & refuses diet, a puke is necessary.”

On Sunday, October 25, Webster was still confined to his room: “My disorder has come to its crisis.” Crisis was then primarily a medical term referring to a change in a disease state—toward either recovery or death. Fortunately, for Webster, it would mean the former.

The following day, Webster felt well enough to assume his role as bridegroom. Presiding over the ceremony at the Greenleafs’ Dorchester home was Pastor Peter Thatcher of Boston’s exclusive Brattle Street Church. (George Washington himself had visited Thatcher’s congregation the day before.) The wedding proceeded, he noted in his diary, without incident: “Much better. This day I became a husband. I have lived a long time a bachelor, something more than 31 years. But I had no person to form a plan for me in early life & direct me to a profession. . . . I am united to an amiable woman, & if I am not happy, shall be much disappointed.” As Webster the expert definer well knew, he hadn’t really been a “bachelor”—a term reserved exclusively for adults—for three decades, but that’s how he felt. Unlike Rebecca, he hadn’t experienced a deep sense of connection with either of his parents as a child. Remarkably, despite his outsize expectations, Rebecca would never let him down. For the next half century, she would provide the emotional anchor that he so desperately needed. Patient and self-controlled, Rebecca, whom her brother Daniel called “an angel,” would nurture her husband with the same dedication as she would the couple’s seven children. Once described by a family member as “neatness and order itself,” she was the perfect match.

On November 7, Webster and his bride moved into Colonel Wadsworth’s house in Hartford. Accompanying the newlyweds was Rebecca’s older sister Priscilla, who would stay for a few months.

The fifth of the fifteen Greenleaf children, “Sister Priscy,” as Webster called her, was as attractive as her seven sisters, but more discriminating about prospective suitors. According to a joke then circulating in Boston, after young clergymen got their license, they typically proposed to Prissy Greenleaf. Before marrying at nearly forty in 1794, she would receive thirty proposals, twenty-three from pastors.

That first month in Hartford was nerve-wracking. The day after their move, Rebecca was stricken with the flu, and Priscilla the next day. On Sunday the fifteenth, Webster had to stay home from church to tend to them. The following Sunday, he went with Priscilla because Rebecca hadn’t yet recovered. Rebecca soon improved, and despite violent storms, Webster and the two Greenleaf sisters managed to travel back and forth to his parents’ home for a Thanksgiving meal on Thursday, November 26 (the first federal celebration). As Rebecca put it in a letter to her brother John, Webster enjoyed “demolishing” the eleven pumpkin puddings she baked. Webster’s mother was initially standoffish with his new bride; the farmer’s wife didn’t know what to make of the sophisticated city girl’s elegant outfits, such as her green brocade featuring pink and red roses. But as Mercy Webster taught her new daughter-in-law how to knit, the two women began to warm up to each other.

Rebecca missed the familiar surroundings of Boston. On December 4, she wrote to her brother John, “Yesterday, I was terrible homesick, and did nothing but bawl the whole day . . . & husband was out almost the whole time. Today the sun shines clear and the world wears a different appearance.” While Rebecca continued to have occasional bouts of gloominess, Webster was in a state of wedded bliss. “[Your sister Becca] is all that is kind and amiable,” he observed to her brother James on Christmas Day, “and you may rest assured that I now realize all my former ideas of her worth. I may safely say that our happiness is not exceeded in the world; for so far as our hearts are concerned, our happiness is without alloy.” However, Webster was still dogged by financial anxiety. In that Christmas letter, he also asked James for another infusion of money. According to his account, the newlyweds were experiencing a sudden two-hundred-dollar shortfall because Rebecca had insisted on buying some extravagances such as chintz furniture: “The deficiency however was to me wholly unexpected, till a short time before our union, and when I informed your sister, she cried as if to break her little heart.” Webster may well have been embellishing (or creating) the drama to plead his case; Rebecca’s version of this incident doesn’t exist.

Webster’s Yale mentor John Trumbull offers a more plausible explanation for the source of his money troubles. In a letter that December to Webster’s classmate Oliver Wolcott, then Connecticut’s comptroller, Trumbull observed, “Webster has returned, and brought with him a very pretty wife. I wish him success; but I doubt, in the present decay of business in our profession [law], whether his profits will enable him to keep up the style he sets out with. I fear he will breakfast upon Institutes, dine upon Dissertations and go to bed supperless.” While Webster’s descendants have long denied that his law practice in Hartford in the early 1790s was anything but lucrative, he would indeed struggle to provide for his new wife. As he acknowledged in his memoir, “[NW] began housekeeping with very unfavorable prospects.” In the end, he would never be able to make a living as a lawyer.

In addition to financial stress, Webster also was experiencing a surge in existential angst. Though Webster had assured the Greenleafs that he would stop writing, just a few weeks after his wedding he realized that he couldn’t keep this pledge. After all, literary activity was what made him feel most alive. For the next few years, Webster the lawyer and family man would be in constant conflict with Webster the scribe. But he typically kept this tension to himself. In a letter to George Washington written less than a year after his marriage, he noted: “I have written much more than any other man of my age in favor of the Revolution and my country. . . . [However], I wish now to attend solely to my profession and to be unknown in any other sphere of life.” While Webster would stop drawing attention to himself as a writer, he wouldn’t stop writing. To resolve his dilemma, he ceased putting his own name on his new literary projects.

IN LATE 1789, Webster joined a legal club whose members included such friends as Trumbull, Wadsworth, Chauncey Goodrich, later a U.S. senator, and Peter Colt, the state treasurer. At weekly dinners, the group would discuss the pressing policy issues of the day. In a December meeting at Trumbull’s house, the question was whether the state’s excise tax on the retail sale or use of imported goods was consistent with the Constitution. As in the 1784 debate over taxes, while the state’s agrarian elements supported the excise tax, its shopkeepers were up in arms. With neighboring states levying no such tax, Connecticut’s consumers had an incentive to shop elsewhere. The area’s leading merchants such as Wadsworth soon petitioned Webster to take up his pen to articulate their concerns.

A week after the dinner at Trumbull’s, Webster spent two nights working on an eighteen-page pamphlet, “Attention! Or New Thoughts on a Serious Subject: Being an Inquiry into the Excise Laws of Connecticut,” which he published in late December under the pseudonym “A Private Citizen.” Addressed to “the Freemen of Connecticut,” Webster’s anonymous article also circulated widely in Connecticut and Massachusetts newspapers over the next few months.

The future lexicographer was in full view. At the heart of the matter was the interpretation of a single sentence in the tenth section of Article I of the Constitution, which stated that “No state shall, without the consent of Congress, lay any imposts or duties on imports or exports, except what may be absolutely necessary for executing its inspecting laws.” The bulk of Webster’s essay focused on defining these key terms. To frame the debate, he began by alluding to “the best compilers of dictionaries” who “explain impost to be any tax, toll or tribute.” Webster noted that Malachi Postlethwaite (author of the mid-eighteenth-century British classic Universal Dictionary of Trade and Commerce) “defines impost to be ‘a tax or duty laid by the sovereign authority.’ . . . It does not appear by this definition that a particular mode of levying and collecting a tax is necessary to constitute it as an impost.” He then elaborated on the true meaning of the words “imports” and “exports.” For example, he asked hypothetical questions about when exactly goods shipped from abroad lose the name of “imports”: “Is it when they are landed? When they are opened? Or when they are sold to the retailer?” Webster continued to split such hairs for another ten pages before concluding that Connecticut’s excise tax was inconsistent with both the letter and the spirit of the Constitution. As in the 1784 impost debate, Webster again identified himself with the cause of national unity. This tax, he contended, ran the risk of “defeating the commerce of America, and perpetuates the life of the monster with thirteen heads.” Thanks to Webster’s fierce advocacy, the state legislature repealed this statute by a nearly unanimous vote in late May.

As 1790 began, Webster’s mood remained upbeat. He published an anonymous New Year’s poem, in which he celebrated the dawn of a new era in America, but he issued the following proviso:

But all must first their station fix, 

Nor craze their skulls with politics; 

His proper calling each pursue, 

And thus his worth and wisdom show.

According to Webster, what America now needed was to get organized. While astronomers, he wrote, had to churn out their almanacs, pedagogues had to teach and parsons had to preach. But Webster didn’t yet have his own niche. While he took on occasional legal assignments, such as drafting writs for clients, his new profession was hardly keeping him busy. “Little business done,” his summary of May 14, was a typical journal entry. Better than expected sales from his books were keeping him afloat. His initial predictions for the arc of his legal career had been overly optimistic. As he reported to James Greenleaf, “The business of lawyers is at a lower ebb than was ever known before . . . some who have been in business ten years scarcely maintain their families.” Webster hoped to get by on his royalties and to wait it out until “we can push off some of the old lawyers.”

That spring and summer, Webster managed to find a variety of new outlets for his compulsive energy. Shortly after Benjamin Franklin’s death on April 17, 1790, he returned to the cause of spelling reform, authoring a series of fourteen editorials for The American Mercury (six initialed and the other eight anonymous). These front-page pieces, entitled “Remarks on the English Language,” also alluded to those fine distinctions so dear to Webster’s heart. “One half of the world,” he griped in his second installment, “use words without annexing cleer [sic] ideas to them.” Here he distinguished between “genius” (“the power of invention”) and “great capacity” (“a power of receiving the ideas communicated by others”). In June, he also published his Collection of Essays and Fugitiv Writings, a volume of his old articles, in which he fleshed out his ill-fated scheme to revamp spelling. And at the same time, he took on another concern dear to Franklin—street paving. Back in 1757, concerned about the dirt and mud on Philadelphia’s Market Street, Franklin had backed an elaborate bill to bring order to the entire city. Completed in early May, Webster’s plan for covering Hartford’s streets with hard stone would prove, as he proudly noted in his diary, “pleasing to many.” For the next few years, a local tax of fourpence on the pound supported Webster’s measure.

And once the warm weather came, Webster also enjoyed tilling the soil. As he noted in a short article, published that June, “The Farmer’s Catechism,” he considered farming “the most necessary, the most healthy, the most innocent and the most agreeable employment of men.” In the garden behind his kitchen, he planted potatoes, beets, carrots, parsnips and cucumbers. Webster loved classifying and arranging potatoes as much as words. On June 25, he performed the following experiment: “Lay 3 square yards of mellow earth with seed potatoes about 8 inches apart, cover them with half rotten hay and straw, cover 1 yard with shoots broken off from the potatoes.” Webster’s passion for the potato would work its way into his dictionary, where he defined it as “one of the cheapest and most nourishing species of vegetable food. . . . In the British dominions and in the United States, it has proved one of the greatest blessings bestowed on man by the Creator.”

On Saturday, July 24, 1790, William and Mary Greenleaf arrived in Hartford. The reason for this visit, as Rebecca’s brother Daniel explained to Webster, was their hope of “being present at a grand launching on Monday [the 26th] . . . which day completes nine months since your marriage.” The Websters’ first child was indeed on its way, but the baby arrived slightly behind schedule. On Monday, August 2, Rebecca became ill and for the next two days, was incapacitated by crippling pain. Finally, at half past four on the fourth, as Webster noted in his diary, his daughter came into the world. The difficult birth would force him to hire a nurse for the month that Rebecca remained bedridden. The Websters called the baby Emily Scholten (adding the middle name in homage to the Dutch wife of James Greenleaf). The following Monday, “Papa and Mama,” as Webster referred to the Greenleafs in his diary, went back to Boston. By the middle of 1790, Webster was feeling closer to his in-laws than to his own parents, who were undergoing a new round of misfortunes. In April, they were forced to sell the West Division farm and move into a house in Hartford with Webster’s sister Mercy and her husband, John Belding. Though occasionally sending his father money, Webster was as financially strapped as ever. In late August, he was reduced to borrowing eighty-five dollars from a friend, Benjamin West, to cover living expenses.

While Webster wasn’t a successful attorney, he was a prominent one. On Friday, October 22, 1790, the U.S. Supreme Court came to Hartford—for its first century, its justices would “ride circuit”—and a few days later, in a ceremony presided over by Chief Justice John Jay, Webster was one of about ten local attorneys admitted to practice in the district court. Webster and Jay were destined to become lifelong friends. That Sunday, Webster also enjoyed socializing with Associate Justice William Cushing (known in history books as the last American jurist to wear a wig).

On Tuesday, October 26, Webster celebrated his first wedding anniversary: “One year past, and no quarelling.” This domestic peace would endure, but Rebecca would usually be the one doing the compromising. As one of the couple’s children would later note in a memoir, “I never knew my mother [to] argue a point with my father. She would express an opinion and defer to him as the best judge of matters.”

In December, Webster began a new writing project, which he kept secret from his family and friends. In a series of twenty anonymous essays, published weekly in The Connecticut Courant, he would address the frustrations of everyday life. Like a stage prompter who helps actors remember their lines, Webster was hoping to “prompt the numerous actors upon the great theater of life.” As he asserted in the introduction to the book version, The Prompter; or A Commentary on Common Sayings and Subjects, released in October of 1791, “He [the writer] cast about to find the method of writing calculated to do the most general good. He wanted to whip vice and folly out of the country.” Patterning himself after Benjamin Franklin’s Poor Richard, Webster eschewed “a pompous elegance of diction.” This anonymous alter ego bore little relation to Webster’s everyday personality; in one essay, he even mocked “learned word-mongers.” He would talk directly to the common man. “Vulgar sayings and proverbs, so much despised by the literary epicures are . . . the pith and marrow of science.” With his speller teaching America’s children how to read, and his Prompter its uneducated masses how to live, few Americans could now escape Webster’s pedagogical influence.

The Prompter was motivated by the same internal pressures that would drive all his literary efforts. This lover of order relished the challenge of organizing information in a clear and useful way. Noting that “there is nothing new in the field of knowledge” and that everything has been said before, the expert compiler and arranger dispensed homespun advice by making “common things appear new.” While in his various books on language he aimed to fix the wrongs of previous lexicographers and grammarians, here he sought to set all of humanity aright, choosing as his epigraph a verse from Pope’s Essay on Man: “To see all others’ faults and feel our own.”

Claiming to be an objective purveyor of truth, Webster concluded his anonymous introduction by assuring his readers that “there is not in this book one personal reflection.” But this volume was actually overflowing with his own feelings and experiences. Consider “Prompter No. II,” published on December 13, 1790, and called “The Fidgets.” The chronically nervous Webster embodied the concept, which he would define in 1828 as a “vulgar” term for restlessness. In this uncharacteristically amusing essay, Webster argued that the disorder was not uncommon: “A man who is fairly hyp’d and a histericky woman are remarkable for fidgets. . . . But those who think these are the only people who have the fidgets think wide of the truth.” Webster went on to identify its various subspecies: domestic fidgets, political fidgets and the purse fidgets, which he called “the most laughable.” He noted that lawyers often manifested symptoms of this particular malady when they shouted out “adjournment—continuance—false—my client is wronged—I’ll have a new trial.” This comic aside reflected his concerns about whether his day job would ever pay his bills.

Despite the pressing need to unburden himself of his own obsessions, in The Prompter, as in the speller and, later, in the dictionary, Webster still connected with the reader. Americans liked his mixture of satire and practical advice. Though a razor-sharp analytic thinker, Webster also had a common touch. No uppity aristocrat, this pugnacious Federalist had a knack for distilling human experience. In the article “When a Man is going down hill, everyone gives him a kick,” Webster captured the anxiety felt by legions of Americans: “While a man is doing very well, that is, while his credit is good, every one helps him—the moment he is pressed for money, however honest and able he may be, he gets kicks from all quarters.” In January 1796, Webster finally revealed himself as the author. Several months later, the Harvard-educated journalist Joseph Dennie, later dubbed the “father of American Belles-Lettres” by Timothy Dwight, sent him a copy of his own influential collection of essays, The Lay Preacher, enclosing the tribute, “I have been amused by The Prompter. The simplicity and ease of style of that little volume taught me the value of the Franklin Style. . . . consider the author as your debtor.” Two years later, a British edition appeared with the following editor’s note: “Americanisms have been retained, as it would have been uncandid to cover American ground with English leaves.” Of its success across the pond, Webster was particularly proud. “In an English notice of the little book,” he wrote in his memoir, “it was said to be a very good shilling-worth publication.” Webster’s book would remain popular for decades; by the mid-nineteenth century, millions of readers would devour a total of one hundred editions.

Will be happy to receive from gentlemen in other states any orders for business, either in his professional or business capacity, and will execute them with fidelity and promptitude.

SO RAN THE AD that Noah Webster, Jr., attorney and counselor at law, placed a couple of times in The New York Daily Advertiser in August 1791. With his Hartford shingle not drawing in enough clients, Webster felt compelled to cast a wider net. And a month earlier, he had personally met with Connecticut’s Governor Samuel Huntington in Norwich, who had helped him add “notary public” to his titles. But despite his tenacious efforts, business would not pick up. Fantasizing about a magical solution to his financial woes, Webster would continue to buy the occasional lottery ticket.

He also took recourse in a source of comfort that he had first discovered as a preadolescent, pouring out his frustrations in letters to the editor. In September 1791, one of his alter egos dashed off a jeremiad to The New York Daily Advertiser, which was reprinted in various New England papers later that fall. Purporting to be from New York, “P.Q.” addressed a series of unrelated pet peeves that had cropped up during his recent travels in three “sister states”—Rhode Island, Massachusetts and Connecticut (Webster himself had hopped around New England that summer). While Newport irked him because “the houses are falling to pieces and deserted,” he was surprised that Bay Sate residents were allowed to sue one another in any county: “How the wise state of Massachusetts can indulge such laws, I leave others to conjecture.” But “P.Q.” reserved his harshest words for Connecticut’s chief justice, Colonel Eliphalet Dyer (whom Webster knew socially): “He had such confusion of ideas or of language that I thought no mortal could understand him; and I found the by-standers were all as much puzzled to understand him as myself.” For Webster, the realization that having a way with words wouldn’t necessarily help him rise in his new profession was devastating. “P.Q.” also expressed frustration with other aspects of Connecticut life: the pews in its churches tended to be just four feet long, requiring ten people to crowd on top of one another. “All must sit like statues,” he complained. Likewise, writing as “Peter Puzzle” in the Courant a few months later, Webster unleashed his fury on other parts of the nation besides New England. He attacked the Senate as “an aristocratic junto,” Southerners for their “microscopic minds” and Washington’s would-be successors, predicting that “nine tenths of our future Presidents will be clear devils.”

But this latest string of disappointments might not have led to so much anger had his own future looked brighter. Webster, who had hardly enjoyed a moment of financial stability since his abrupt exit from his father’s farmhouse, was feeling despondent. He confided his troubles to James Greenleaf, who responded the following January from Amsterdam: “I am sorry to observe in your last something that borders on a depression of spirits. . . . If you are not so rich as you wish to be or even as you are conscious of deserving, you have on the other hand such domestic happiness as falls to the lot of but few.” Unable to find much gainful employment for himself, Webster turned his attention to the welfare of others. On January 2, 1792, the Courant published Webster’s “New Year’s Gift”—the first of a new series of eight weekly essays called “The Patriot” and subtitled “On the means of improving the natural advantages of Connecticut and promoting the prosperity of its inhabitants.” Webster addressed a wide range of pressing economic issues including trade, transportation and global warming, a subject he would come back to in a treatise a half-dozen years later. And in a front-page column on January 23, Webster highlighted the need for his hometown to have its own bank: “For want of specie, articles in market must be bartered—and barter is a public and private calamity.” Webster’s thesis was well taken; after all, the cash-strapped lawyer was himself prone to rely on “this instrument of knavery.” (Several years earlier, when Hartford’s First Episcopal Church was raising capital, Webster had contributed three pounds in the form of seven dozen of his spellers.) Soon after publishing this influential article on the utility of banks, Webster—along with John Trumbull and Chauncey Goodrich—drafted the petition to establish the Hartford Bank, which was approved by the state legislature in May.

Webster’s increasing civic commitment manifested itself in other ways as well. In late March, he was elected to be a member of Hartford’s governing body, its Common Council. He also began to take a keen interest in the plight of the city’s underclass. “But there are in every town, more especially in Hartford, great numbers of mechanics and other laborers . . . who . . . have no means of subsistence but their daily earnings,” he wrote in an anonymous piece published in December 1791 in the Courant, in which he proposed establishing a Charitable Society of Hartford. Webster would devote considerable energy to realizing this vision. The following year, he helped draft the group’s constitution and became its secretary. By 1793, the Charitable Society, which relied on small contributions—a dollar or more—from employers for each worker, was up and running. Thanks to Webster, his hometown established a social insurance system for the poor, sick and disabled some hundred and forty years before Roosevelt’s New Deal.

Webster also took up the cause of another segment of the downtrodden—slaves. In May 1791, he became a charter member of Connecticut’s abolitionist society. On May 9, 1793, he gave the third annual address at the state’s Society for the Promotion of Freedom, which he expanded into a fifty-page treatise, Effects of Slavery on Morals and Industry, published later that year. As he noted in his preface, Webster had wanted to put together his thoughts on slavery for years. As befit his sensibility, Webster’s critique hinged on a utilitarian argument: “The exercise of uncontrolled power, always gives a peculiar complexion to the manners, passion and conversation both of the oppressor and the oppressed.” As a result, this “barbarous and wicked” institution, he asserted, was bound to exert pernicious effects not only on “the blacks in the United States,” but also on the nation as a whole. To buttress his claim that slavery’s stupefying influence can be traced back to the far reaches of history, Webster put forth a philological analysis: “It is remarkable that the word lazzi, which among our Saxon ancestors was the denomination or the lowest order of bondmen or servants, is the origin of our English word lazy. . . . If slavery had this effect upon our own ancestors . . . surely modern philosophers need not resort to an original difference of race for the cause of that . . . want of mental vigor. . . . in the enslaved. . . .” According to Webster, etymology cast “a flood of light” not only on language but also on history. Yet Webster’s etymological investigations, to which he would later devote an entire decade of his life, would be the weakest link in his oeuvre. The rigorous definer had a penchant for making wild guesses about the roots of words; in fact, there is no such word as “lazzi” in Anglo-Saxon, a language which has no “z’s.”3 Nevertheless, the supremely self-confident Webster was convinced that his linguistic backtracking supplied definitive proof of his sociological assumptions.

Despite his abhorrence of slavery, Webster feared “total sudden abolition.” To make his case, Webster went back to the demographic data that he had first gathered during his trans-American odyssey. He looked at how the nation’s seven hundred thousand slaves—out of a population of four million—were sprinkled across the country. While the ratio of slaves to free inhabitants in New England was 1 to 190, in the six southern states it was 1 to 2.5. “An attempt to eradicate it [slavery],” Webster concluded, “at a single blow would expose the political body to dissolution.” Decades later, a more conservative Webster would express nothing but contempt for New England’s Abolitionists. In 1837, he wrote to one of his children, “They are absolutely deranged. . . . slavery is a great sin and a great calamity, but it is not our sin.”

As Webster was polishing up his antislavery treatise, his legal career was falling apart. As he later recalled, “In 1793, N. W. found that his professional business, with small emoluments of his office of Notary Public was not adequate to the support of his family. . . . He then began to contemplate a change of business.” Now the thirty-four-year-old father of two—his second daughter, Frances Juliana, was born in February 1793—Webster became frantic; he was willing to consider anything. He thought about running a farm. He was also open to the suggestion, raised by his brother-in-law Dr. Nathaniel Appleton, of taking over the Boston Book Store. On June 24, 1793, he wrote James Greenleaf, who had recently returned from Amsterdam, of his internal deliberations: “All I ask (or ever wished) is business, and whether on a large or small scale I will be satisfied with it. To renounce all my literary pursuits, which are now very congenial with my habits, would not be altogether agreeable; but it would not make me unhappy.” Four years into his marriage, Webster was still willing to give up his beloved words for his wife.

Webster kept Greenleaf abreast of his possible career moves because he figured he could count on his brother-in-law for further financial help. And with good reason. Like a contemporary hedge-fund manager, Greenleaf had vast sums of money under his control. Though Webster wasn’t privy to the details, between 1789 and 1792, the speculator (along with his business partner Watson, then also a director at the new Bank of the United States) had secured from Dutch investors a series of twelve loans totaling $1.3 million—equivalent to roughly $400 million today. And that March, Greenleaf had also been appointed U.S. Consul to Amsterdam. Approaching thirty, Rebecca’s older brother, who would soon abandon his Dutch wife and children, was emerging as an internationally renowned business leader. The five-foot-seven, hundred-forty-pounder with the ruddy complexion cut a dashing figure with his gray eyes and powdered wig. In 1795, the same year that Gilbert Stuart painted Greenleaf’s portrait, Abigail Adams observed, “The girls here, I believe, wish his wife dead. He is sufficiently a favorite wherever he goes.”

As with previous benefactors, Webster was open about the dire nature of his financial situation. In a letter to his brother-in-law dated July 8, 1793, Webster noted that his debts came to a total of $1,815 (roughly $545,000 in today’s dollars). As Webster explained, about half that amount “grew out of the expenses of my education (which contributed to involve my father & finally to ruin him) out of the expenses of my Southern Tour in 1785—& out of the expenses incurred by publishing my Dissertations in 1789.” Another five hundred dollars (which was then a typical annual salary for a lawyer) was owed to other Greenleafs—Rebecca’s father and her older brother Daniel. But the actual amount of Webster’s indebtedness was far greater, since he no longer included in his calculations James Greenleaf’s many loans, which he had initially promised to repay at a hefty interest rate. As an embarrassed Webster concluded, “This is a short statement of my affairs, & nearly correct as I can make it. . . . It is bad enough in all conscience; it is a situation that has made me very unhappy.” While Webster was owed $680 and held a valuable asset—the New York copyright of his speller—he was despondent about getting out of debt anytime soon.


The twelfth child of William and Mary Greenleaf, James Greenleaf (1765-1843) was a year older than Webster’s wife, Rebecca. Without the financial assistance of the well-heeled “brother James,” Webster could not have married and started a family.

Throughout what he called “the hottest summer ever known,” Webster kept thinking about how he could make more money. On July 24, he noted in his diary, “We have squashes from our garden and watermelons in market.”

But a national crisis would again knock Webster out of his doldrums. Edmond Genet, the French ambassador to the United States, was stepping up his efforts to drag America into another war with England. To keep America at peace, George Washington would once again turn to his trusted protégé. And Webster would soon be able to earn a good living by writing a torrent of words on behalf of his country. Nothing could have pleased him more.

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