Webster's brother-in-law, James Greenleaf, (1765-1843) was a wealthy speculator who provided the struggling writer with the money to get married and start a family. After a series of land deals went sour, Greenleaf landed in Philadelphia's Prune Street Debtors' Prison in 1798.

Q: What drew you to Webster? What made you want to tell his story yourself and how does your biography differ from others already published?
A: I have a strong personal connection to Webster. Yale also inculcated in me a love of learning; after enjoying a dose of heady intellectual life in New Haven, I too faced the challenge of figuring out how to establish myself as a writer. When Webster turned twenty, his father handed him an $8 bill, which, during the hyperinflation of 1778, was nearly worthless. The bedraggled Hartford farmer then proceeded to inform his son that he was “on his own;” as Webster later put it in his memoir, he immediately “felt cast upon the world.” A little more than 200 Yale graduations later, my father, a hard-charging Wall Street exec, also failed to encourage my literary aspirations. As America’s first freelance writer — and one of its most successful — Webster has been a frequent source of inspiration.
While most previous biographies have painted Webster as an American saint, I was interested in capturing his complex personality. He was a bundle of contradictions. Loner and accomplished networker. Revolutionary and reactionary. Womanizer and prig. Given that this non-stop writer kept a lively diary, I was excited by the chance to get inside his head and to show what made him tick.

Q: Did you always see him as having such an impact on the growth of American culture and sensibility? Or were you surprised to find out how much influence he had?
A: Before beginning the research, which eventually led me to about twenty archive libraries up and down the east coast, I had assumed that Webster was just a word-nerd who sequestered himself in his sand-lined study for decades to labor on the dictionary. I was surprised to discover that his magnum opus — the American Dictionary, first published in 1828 — constituted the last act of a long career dedicated to both words and public service. By then, he was a national celebrity who had already shaped many aspects of American culture, ranging from education, science and journalism to language and the very nature of our political institutions.

Q: Webster rubbed shoulders with a number of our nation’s founding fathers — Washington, Franklin, and Hamilton, among others — and identified strongly in his youth with the Federalist cause. Which of his associations had the most marked influence on his ideas about nationhood and American government? In what ways did he influence the founders?
A: Webster attended college during the early years of the War for Independence; the summer before his senior year, he fought at the Battle of Saratoga. At Yale, he came under the influence of a young professor, Timothy Dwight, later the college’s president, who impressed upon him the need for Americans to unite behind a national identity. For the rest of his life, Webster urged Americans to think of themselves as Americans rather than as residents of a particular state or immigrants tied to their country of origin.
This fierce pride in all things American was the thread that linked all of his work. And even though he was at least fifteen younger than most of the key Founders, he influenced them — rather than the other way around. As I describe in the prologue, as a twenty-six year-old whippersnapper, he gave George Washington himself a civic lessons. When Washington told Webster that he had reached out to a friend in Scotland to find a tutor for his step-grandchildren, the young writer was aghast, noting that we should not look to Europe for our teachers. “America,” Webster insisted, “must be as independent in literature as she is in politics, as famous for arts as for arms.”

Q: You don’t shy away from making assertions about the psychological pathologies that drove Webster. What are the bases for these claims? How do you think a modern psychologist would characterize Webster?
A: Webster was quite open in his diary and letters about his inner turmoil. While he lived in a pre-psychological age in which there was no DSM — psychiatry’s massive diagnostic manual — he frequently used words like “depression,” “anxiety” and “nervous affections” to describe his mental state. As I suggest, a modern-day psychologist might be inclined to diagnose him with obsessive-compulsive personality disorder (OCPD). While this condition is related to obsessive-compulsive disorder (OCD), it’s not the same thing. Unlike those with OCD who often become incapacitated by their anxiety — for example, they might compelled to check dozens of times that they turned off the stove — people with OCPD typically function “better than well.” Webster’s obsessionality gave him the focus to devote endless hours to compiling and defining words. And while he lived a full and vibrant life, his inflexibility — stubbornness and a lack of empathy are the hallmarks of this character disorder — took a toll on his wife and seven children. As therapists know all too well, domineering obsessionals often drive other family members to seek psychiatric treatment.

Q: Webster’s Speller was not only one of the most influential educational books of the 18th and 19th Centuries, but also a mega-bestseller before the term existed. What made the book so popular and why did Webster continue to struggle with money despite its success?

A: While Webster’s chronic anxiety made it difficult for him to connect with other people, he had a remarkable knack for connecting with the reader. His legendary American Spelling Book, which essentially taught reading rather than spelling, was user-friendly; it communicated the nuts and bolts of English in a manner that children could easily understand. While Webster made an enormous amount of money from the book — in 1816, he landed America’s first blockbuster book deal which promised him $ 42,000 over a 14-year period — he could have made even more. What caused his money troubles was that at the age of forty, he retired so that he could devote himself full-time to his dictionary. And because he was so dependent on the income from his speller, he didn’t strike hard bargains with his publishers. Thus, a year after signing that hefty contract, he caved in and asked for all the money upfront, settling for a total of $ 23,000.

Q: Your first book examined the life of Peter Mark Roget. How would you compare the two men?

A: Roget and Webster had a similar make-up; both men felt more comfortable in the company of words rather than people. Organizing the English language was for both this Founding Father and this Victorian physician a form of therapy, which provided an emotional anchor. Surprisingly, though both lexicographers were enormously gifted wordsmiths, each man lacked a literary sensibility. Unlike Samuel Johnson, who published the first great English dictionary in 1755, neither Webster nor Roget cared much for poetry, fiction or drama. While not a medical school graduate like Roget, Webster was also more at home in the world of science — right before starting the dictionary, he polished off a 1000-page treatise on epidemiology.
Their careers ran on parallel tracks. Both men had expensive tastes and tried to solidify their finances in the same way — by finding a rich wife. “When you marry,” Webster advised his children, “look out for the stock.” And Roget’s Thesaurus, like Webster’s Dictionary, was also a retirement project. Roget started it in earnest at the age of 73 after he had both given up his medical practice and resigned from his lofty position as Secretary of the Royal Society, England’s foremost scientific organization.

Q: Webster was involved in a wide variety of pursuits before beginning work on the dictionary in earnest. Can you give an overview of some of his most noteworthy achievements?

A: In 1782, when Webster finished his speller, the Articles of Confederation were still the law of the land. To protect his asset, he became the father of American copyright law; he personally went to all the thirteen state capitals to ensure passage of the requisite legislation. His other early achievements include cranking out pamphlets in support of the Constitution. In 1785, he published “Sketches of American Policy,” which argued for the need for a stronger central government by famously noting that “our union is but a name and our confederation a web.” Several years later, at the behest of George Washington, he became the editor of New York City’s first daily newspaper, American Minerva. While living in Manhattan, the highly influential Federalist journalist began working on a series of books on “the yellow fever,” the plague that would terrorize America’s city dwellers throughout the 1790s. Thus, he also helped to give birth to modern public health research. In the early 1800s, he served as a state legislator in both Connecticut and Massachusetts. A progressive pedagogue, who championed both female education and public schools, he also helped to found Amherst College.

Q: How long did it take Webster to complete his dictionary? How did he approach such a mammoth undertaking, and how did he draw from the work of Samuel Johnson and other lexicographers? How did his work differ from his predecessors?
A: Webster began his dictionary in 1800 soon after he settled in the New Haven mansion formerly owned by Benedict Arnold. (Due to the stigma associated with living there, he got a good deal, paying only $ 2666.66). He would keep working on various versions of the dictionary until the day he died in 1843. Webster sought to make obsolete the works of both Samuel Johnson and Samuel Johnson, Jr. This other Johnson was no relation to the erudite Brit, but a school teacher from Connecticut who had compiled a small dictionary – most of the definitions were just one or two words – published in 1798. In 1806, Webster published his answer to Johnson Jr, his Compendious Dictionary of the English Language — compendious means brief — which was a warm-up exercise for the unabridged dictionary of 1828. To write his American Dictionary, Webster leaned on Johnson as well as on the major Latin-English Dictionary of the day by Robert Ainsworth. I examined the original manuscripts pages at several archives, including the Morgan Library and the New Haven Museum. At the New York Public Library, I also studied Webster’s copy of the 1799 version of Johnson’s Dictionary which he consulted frequently. Next to many of Johnson’s Shakespeare quotations, which were used to illustrate the meanings of words, Webster put a little black mark. In contrast to Johnson, Webster rarely cited Shakespeare. Instead he would insert “Shak” into the definitions of many dirty words such as “bastard” and “strumpet,” as if he were blaming the Bard of Avon himself for the world’s unwholesome characters. Webster’s hatred of Shakespeare dated back to his Yale days when undergraduates were fined for attending the theatre because drama was considered one step away from sex.
While Webster’s text was less literary than Johnson’s, it was more scientific. He included thousands of new terms that had cropped up during the Enlightenment such as “phosphorescent” and “planetarium.” But Webster biggest improvement was not so much in comprehensiveness — though he defined 70,000 words as opposed to the 58,000 of the most recent edition of Johnson — as in precision. Webster transformed definitions from little more than lists of synonymous terms to tightly knit mini-essays, which highlighted fine distinctions. As James Murray, the editor of the OED once put it, Webster “was a born definer.”

Q: You present Webster as a great but flawed man, especially in later years when he seemed to take on views contrary to the freedom and liberty he fought for early on. What do you think accounted for this switch? Did Webster’s views vacillate in other respects?

A: Like his friend and idol, Benjamin Franklin, who once told him, “I have been all my life changing my opinions,” the argumentative Webster was often at war with himself. His constantly shifting positions on policy matters were a reflection of his tempestuous character. Webster might have made a good talking head on Cable TV. He liked to make inflammatory statements. As he entered middle-age, Webster insisted that no American should be allowed to vote until the age of 45.
And Webster became particularly crotchety in old age which he defined as “an aristocracy resulting from God’s appointment.” (Though he often fulminated, Webster did have flashes of wit.) As he was about to turn eighty, he declared that he would rather be a bear and hibernate in winter than “be under the tyranny of our degenerate rulers,” describing Americans as “a degenerate and wicked people.”

Q: Does the modern-day Merriam-Webster bear any resemblance to Webster’s 1828 dictionary? Can you give a brief summary of the ways that Webster’s lexicographical efforts have resonated over the years and into the present?

A: None of the dictionaries that Webster worked on in his lifetime — even the unabridged edition of 1841, which he funded by mortgaging his home at the age of eighty — look like a modern-day dictionary. The English dictionary as we know it was born with the 1864 edition of Webster’s. Widely hailed as a masterpiece in its day, this version of The American Dictionary provided the template for everything that followed in both America and Britain, including the Oxford English Dictionary, whose first volume came out two decades later.
This first major revision of Webster’s, which was edited by Noah Porter along with a team of lexicographers drawn largely from the Yale faculty, fixed the one major gaffe in Webster’s otherwise exemplary oeuvre. Webster’s etymologies were never more than wild guesswork. While philology — the systematic study of language — was still in its infancy during his lifetime, Webster’s self-absorption and stubbornness led him to ignore the important discoveries made by German scholars in the early 19th century.
But with this one exception, Webster’s spirit infuses the contemporary dictionary; that’s why numerous publishers besides Merriam-Webster have slapped his name on the cover. Webster was the first lexicographer to turn his own examples into a central component of definitions. To explain morality, he noted, “We often admire the politeness of men whose morality we question.” Even more important, Webster was a fervent advocate for description over prescription, arguing that dictionaries should reflect language as it is, not how it ought to be. While this position was controversial for a century, it’s been the norm ever since the heyday of the late Phillip Gove, the editor of the massive Webster’s Third, published in 1961. Gove was the one who decided that “ain’t” was acceptable English. Likewise, in calling “refudiate” 2010’s word of the year, The New Oxford American Dictionary was also invoking the legacy of America’s greatest lexicographer.