Irving returned from Europe in early 1806, certain of two things: that he didn’t want to be a lawyer, and that he did want to be a writer … if he only knew how. Until then, the law remained his only viable form of employment, and he applied himself to passing the bar exam—which he did, albeit just barely.
That same year, Irving fell in with a group of moderately successful young men—including Gouverneur Kemble, New York blueblood Henry Brevoort, and James Kirke Paulding— who dubbed themselves the roguish “Lads of Kilkenny.” The Lads spent most of their time socializing, eating late dinners and staggering home drunk. But when pressed by Irving, they could also be remarkably productive—and in January 1807, Irving, Paulding, and Irving’s oldest brother William published the first installment of the satiric magazine Salmagundi.
Poking fun at the politics, social scene, and mores of the time, Salmagundi was the equivalent of Mad magazine to New Yorkers of 1807. A popular success even beyond New York, snooty critics accused its creators of “immoral influence.” Irving was delighted with such notoriety. Twenty issues would be published before squabbles with their publisher brought the magazine to an end.
Salmagundi cancelled, Irving found another topic ripe for satire—a recently-published travelogue called Picture of New York. Progress was slow, however, for he had fallen in love with Judge Hoffman’s 17-year-old daughter, Matilda. For nearly a year, Irving and Matilda carried on their romance, until the spring of 1809, when Matilda died of tuberculosis. Devastated, Irving retreated to a friend’s home in Kinderhook where, ironically, he would complete his finest burlesque while digging his way out of a black depression.
Scrapping his initial idea to parody the travelogue, Irving instead compressed the reams of notes and random scribblings into something new. The resulting book, A History of New York, was no mere parody, but a rollicking, satirical history of the Dutch conquest, establishment, and eventual loss of his home town. In December 1809, Irving published his book under a new pseudonym, Diedrich Knickerbocker, a wry, crusty Dutch historian. An immediate bestseller, Knickerbocker soon became the personification of All Things New York. Even today, it appears across the front of New York’s NBA team, although in its more well-known abbreviated form, reading simply “Knicks.”
Despite his success as Knickerbocker, Irving remained uncertain of his abilities—and for the next few years he cast about trying to determine if he could earn a living as a writer or whether, out of necessity, he would have to find a real job. He eventually landed a post as editor of a new magazine, the Analectic, where, as the War of 1812 raged around him, he patriotically cranked out biographies of America’s naval war heroes. Itching for military glory himself, Irving was delighted to receive a commission to serve as a colonel in the New York State Militia. To his great disappointment, he saw no action.
With the failure of the Analectic in 1814, and the war over, a bored Irving sailed for Liverpool in 1815 to visit his brother, Peter, who was overseeing the family’s shipping business in England—a business, Irving soon learned, that was on the brink of collapse. Irving spent the next two years trying unsuccessfully to dig out the firm, eventually declaring bankruptcy—a humiliating process that would haunt Irving for the rest of his life.