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Isaac Sears and the Roots of America in New York

An 1884 illustration depicts the Battle of Golden Hill, a skirmish between New York's Sons of Liberty and British soldiers garrisoned in Manhattan. The incident preceded the Boston Massacre by six weeks. 

I no longer even hated Rivington Street but the idea of Rivington Street, all Rivington Streets of all nationalities allowed to pile up in cities like gigantic dung heaps smelling up the world, ambitions growing out of filth and crawling away like worms.

—Al Manheim, in Budd Schulberg, what makes sammy run?

Rivington Street on the Lower East Side has been immortalized as a feverish melting pot in novels, ballads, poems, lyrics, films, and even album covers by everyone from the Beastie Boys to Lady Gaga. But in the late 1700s, when it was originally mapped, the street was an anodyne, pastoral expanse sandwiched between Delancey Street and North Street. Later renamed Houston Street, North Street originally defined New York’s urban outer boundary at the time when, since livestock still outnumbered people, the landscape was indeed punctuated by dung heaps, though they were not uncommonly gigantic by eighteenth-century standards.

Rivington and Delancey Streets run parallel (unlike their namesakes). That the street names have endured is further proof that New Yorkers don’t know—or care— much about their history. Given the Anglophobia of the nineteenth century, at least one of them would have been renamed for, among others, Isaac Sears. (There is a two-block-long Sears Street in the borough of Manhattan, on Randalls Island, but it’s named for a firefighter trainee who died in 2008.) Neither Rivington Street’s undistinguished  geography,  nor  its demography,  reflects the gratitude that James De Lancey Jr. intended to convey by naming the thoroughfare for James Rivington. The beleaguered fellow Loyalist and blisteringly pro-British publisher had helped De Lancey dispose of his property once it became apparent that the insufferable British subjugation of New York, which had begun in 1776 and would continue for seven years, could not be sustained indefinitely. All other considerations aside, it’s no surprise that the screenwriter and novelist Budd Schulberg was professionally predisposed to harbor ill will against a street named for a publisher.

Born in London, Rivington emigrated to America in 1760. Thirteen years later, he started publishing the New York Gazetteer. The newspaper began as a relatively objective journal, although Rivington’s  personal  loyalties  were  unconcealed.  A favorite target of his vilification was the merchant patriot provocateur Isaac Sears, whom he maligned as “a tool of the lowest order; a political cracker, sent abroad to alarm and terrify.” Sears gave as good as he got, denouncing Rivington as “a servile tool, ready to do the dirty work of any knave who purchases.”

James De Lancey Jr. was a native New Yorker, his Huguenot grandfather, Stephen, having fled France and arrived in America in 1686. James Jr. inherited the family’s mercantile business and, like many fellow merchants, opposed Parliament’s heavy- handed taxation. James Jr. opposed the Stamp Act and other barriers to the colony’s commerce, a self-serving mindset that temporarily endeared him to the radicals. But he sacrificed his credibility with patriotic Americans by belatedly agreeing to subsidize the care and feeding of British troops under the Quartering Act. Presciently, he packed his belongings and left New York in April 1775 for England, never to return. Historians still debate whether the ensuing conflict was a revolution, a war for independence, or a civil war, and what proportion of Americans—some say more than half—were neither zealous Loyalists nor passionate patriots. The radicals revolting against an unrepresentative government some 3,500 miles away were the most identifiable by their words and deeds. They were dominated in the city by the triumvirate of Isaac Sears, John Lamb, and Alexander McDougall, men who, Pauline Maier wrote in The Old Revolutionaries (1980), were ambitious when “the obscure might rise to positions of power and prominence” through politics and “played the role of brokers, mediating between the various social and economic groups that made up the community.” Lamb, a writer, was the son of a convicted robber exiled from England. McDougall, a Scottish-born merchant, had been a privateer.

Sears, a fifth-generation New Englander, was born in Massachusetts in 1730. When Isaac was four, his family moved to Norwalk, Connecticut. At sixteen he was apprenticed to a captain; at twenty-two, he was already commanding a sloop that shuttled cargo between New York and Canada. He captained a trading vessel until, in the Seven Years’ War, he was commissioned as a privateer. As the Magazine of American History recounts, his exploits “gave him a great moral ascendancy over his fellow-citizens, and he seems to have fairly won over the title of ‘King’. ” By the early 1760s Sears had profited so handsomely as a privateer that he removed to New York, where he invested in trade with the West Indies. He married Sarah Drake, whose father owned the Water Street Tavern, at Trinity Church. Like so many other reluctant revolutionaries in New York, he seemed the antithesis of the rabble in arms that the British identified with the mobocracy.

Boston and Philadelphia would always maintain a friendly rivalry for the status of America’s cradle of liberty; arguably, New York’s role as the amalgamator of competitive colonies into symbiotic states and the site where the nation’s government was invented has often been overlooked. New York was the only one of the thirteen colonies that the British had seized by force rather than settled in the seventeenth century. The nineteenth-century historian Henry B. Dawson dated the first revolt against the crown to as early as 1681, when New York merchants refused to pay custom duties. On October 18, 1764, the Provincial Assembly of New York was first among the colonies—before Massachusetts in 1770, and Virginia in 1773—to appoint a Committee of Correspondence, to collaborate with its legislative counterparts on the East Coast “on the Subject of the impending Dangers which threaten the Colonies of being taxed by Laws to be passed by Great Britain.”

Britain, under a newly crowned king and an equally stubborn prime minister, hamhandedly forced the colonies to foot the lion’s share of their own defense during and after the Seven Years’ War—without giving the English expatriates and their progeny any say in the matter. Worse still, a 1763 proclamation barring American settlement west of the Appalachians, while its bestowal of title on Native Americans made it a legal benchmark of sorts, infuriated land-grabbing colonists, including George Washington, who would own some thirty-two thousand acres within the circumscribed territory. After the war, Parliament asserted its dominion by vigorously enforcing the Navigation Acts, all but granting Britain a monopoly on trade with America. The following spring, Parliament passed the odious Stamp Act. Effective November 1, 1765, the act required that officially stamped paper be purchased for all legal documents and that tax stamps be affixed to everything from pamphlets to playing cards.

On October 7, 1765, barely three weeks before the Stamp Act was to take effect, nine of the thirteen colonies, prodded by Massachusetts and Virginia, dispatched representatives to a Stamp Act Congress, which convened at New York’s city hall. Even as the Congress was still meeting in New York, the first tax stamps were delivered from England on October 23. Sears, McDougall, and Lamb threatened a licking to anyone who used them. On October 25, delegates to the congress signed a fourteen-point Declaration of Rights and Grievances, which affirmed the supremacy of Parliament but argued that the rights of Englishmen precluded the august body from levying taxes because they could only be imposed by representatives of the people. John William Leonard, writing in his History of the City of New York, 1609-1909 (1910), proclaimed the congress “the beginning of the American union.”

On October 31, one day before the Stamp Act was to take effect, the city’s merchants struck an even greater strategic blow against the crown. Two hundred voted unanimously to boycott British goods altogether until the act was repealed. “New York thus led in the great and effective movement which proved to be America’s greatest commercial attack upon Great Britain,” Leonard wrote. Philadelphia merchants followed suit on November 7; Boston’s on December 3. When the underground Sons of Liberty emerged publicly to export its strategy of defiance to other colonies, the first name on its membership roster was Isaac Sears.

It’s debatable whether Sears and many of his compatriots would have been much more amenable to subsidizing British troops had the Stamp Act and similar levies been imposed by legislators duly elected in the colonies instead of by distant, unrepresentative members of Parliament. He and other self-proclaimed patriots insisted, though, that “taxation without representation” was more than a bumper sticker. It was a matter of principle—although, in truth, because of gender, race, and property qualifications, fewer than one third of the colonists were eligible to vote for their own representatives, which meant that some two thirds of the population would have been taxed without direct representation anyway.

On June 4, 1766, the Sons of Liberty convened on the Commons, ostensibly to mark the king’s birthday and celebrate Parliament’s repeal of the Stamp Act by brazenly erecting a flagstaff called a Liberty Pole directly facing the British barracks—a defiant invitation for the Red Coats to topple it, which they did, three times, only to have the colonists immediately replace it. (After the Common Council refused to give the Sons of Liberty permission for another provocation, Sears bought a plot of land nearby and erected a twenty-two-foot totem on his own property.) On January 18, 1770, an altercation between Sears and several British soldiers posting broadsides belittling the Sons of Liberty as “great heroes who thought their freedom depended on a piece of wood” escalated into what became known (but not famous) as the Battle of Golden Hill—for the “golden grain” grown there in Dutch times—in Lower Manhattan. The British, whose broadsides presumably constituted an exercise of their free speech rights, derided the Sons of Liberty as drunken rabble while the soldiers stoically defended the populace. Accounts of casualties during the ensuing clashes varied widely (including possibly one death and several serious injuries). The better-known Boston Massacre occurred six weeks later.

New Yorkers almost beat Boston to a tea party, too. The first shipload of taxed tea was due in New York on November 25, 1773, and the Sons of Liberty were fully prepped to dump the tea chests overboard as soon as they arrived. But the tea-laden vessel was delayed, blown off course in a storm. By the time the ship was finally sighted off Sandy Hook the following April, Boston had stolen New York’s thunder.

Undeterred, Isaac Sears prevented the tea from being marketed in Manhattan. A ditty at the time by the patriot poet Philip Freneau immortalized his exploits in rhyme:

At this time there arose, a certain “King Sears,” Who made it his duty, to banish our fears,

He was, without doubt, a person of merit,

Great knowledge, some wit, and abundance of spirit, Could talk like a lawyer, and that without fee,

And threaten’ d perdition, to all that drank Tea.

A year later, in April 1775, Sears was publicly advocating revolution, a defiant act of sedition that inevitably resulted in his arrest. Freed from prison by fellow patriots who paraded him triumphantly through the city’s streets, Sears and his allies commandeered city hall, where they seized five hundred muskets that had recently arrived from England for shipment to British troops in Boston. Less than a week later, Sears and a small army of 350 men raided the custom house, where duties were collected on imports, seized control, and proclaimed that the Port of New York was closed.

The following November, for the second time, Sears violently suppressed free speech—a right that had been won by the printer Peter Zenger when he was acquitted of libeling the royal governor in 1735. (He was tried at New York’s city hall, where in 1789 the First Amendment, which would be enshrined in the Bill of Rights, was approved by Congress and sent to the states for ratification.) After Sears learned that the British governor of Virginia had seized a printing press operated by the nephew of John Holt, the patriot New York publisher, he mobilized a vigilante posse that raided the offices of Rivington’s Gazetteer. The mob confiscated the newspaper’s lead type, recasting it as bullets. (So much for the pen being mightier than the sword.) “Though I am fully sensible how dangerous and pernicious Rivington’s press has been,” Alexander Hamilton complained to John Jay, “I cannot help disapproving and condemning this step.”

Sears repaired to New Haven, then forayed episodically into New York, where he forced Loyalists, including the Reverend Samuel Seabury (the future first American Episcopal bishop), to swear allegiance to the “United States of America.” If, by the spring of 1776, the mission could be judged a success, a Connecticut delegate to the Continental Congress wrote to Samuel Adams, it was “much owing to that Crazy Capt. Sears.” Sears appropriated a British cannon from the Battery and sabotaged efforts to resupply British warships. Infuriated, Vice Admiral Samuel Graves ordered the sixty-four-gun HMS Asia to “fire upon the House of that Traitor, Sears.”

That July 9, after Washington read the newly printed Declaration of Independence to his troops in New York, Sears mustered a mob of patriots to march the mile and a half downtown to Bowling Green, where they lassoed the two-ton statue of King George III, toppled it, cleaved it into portable segments, and carted off most of the gilded lead remnants to Litchfield, Connecticut, to be melted and delivered back to the British in the form of 42,088 musket balls. Toppling an effigy was one thing, but another of Sears’s extremist provocations that same month proved too much: Washington himself thwarted the arrest of William Tryon, New York’s royal governor. (Ironically, Tryon would conspire in a bollixed scheme to kidnap Washington the following spring.)


Excerpted from The New Yorkers: 31 Remarkable People, 400 Years, and the Untold Biography of the World's Greatest City. Used with the permission of the publisher, Bloomsbury. Copyright © 2022 by Sam Roberts.