In late summer 1765, a group of Boston artisans, shopkeepers, and businessmen formed a group known as the Loyal Nine to oppose the Stamp Act. The Loyal Nine planned to lead the public in forcing stamp distributors, who alone could collect money for stamped paper, to resign before taxes were due on November 1, 1765.

Bostonians were in the habit of congregating in large groups to express themselves politically. On certain festival days it was not uncommon for large crowds from the North End and South End of the city to converge upon each other, throwing stones and whatever else they could find, and engaging in rowdy fistfights. The Loyal Nine, in an effort to harness the power of both groups, oversaw a truce between the two groups, which were united under the leadership of a South End shoemaker, Ebeneezer MacIntosh.

On the morning of August 14, 1765, Bostonians awoke to find an effigy of stamp collector Andrew Oliver hanged from a tree. Oliver did not take the hint to resign immediately, so at dusk, MacIntosh led several hundred men in destroying a new building that Oliver owned. At this point the Loyal Nine disappeared, and the mob moved on without their controlling influence. They demonstrated outside Oliver's house, "stamping" his effigy to pieces. They then ransacked his house, destroying it. Lieutenant Governor Thomas Hutchinson arrived with the sheriff driving off the mob with a barrage of stones. Oliver resigned.

Violence was contagious in the colonies. Twelve days later, Hutchinson's home was destroyed as well. Violence next struck in Newport, Rhode Island, where a crowd organized by local merchants grew beyond control. The crowd burned effigies and destroyed the homes of three stamp distributors, and then turned against the merchants. A sailor named John Webber assumed control, and threatened to destroy the merchants' homes and warehouses if they did not pay an enormous sum. He was caught and jailed before any destruction took place.

Political dissent became organized quickly. Groups calling themselves the Sons of Liberty formed throughout the colonies to control the widespread violence. They directed violent demonstrations against property rather than individuals, and ensured that no one was killed. They forbade their followers to carry weapons, and used military formations to maneuver large crowds. On October 7, 1765, representatives of nine colonial assemblies met in New York City, at the Stamp Act Congress. The colonies agreed widely on the principles that Parliament could not tax anyone outside of Great Britain, and could not deny anyone a fair trial, both of which had been done in the American colonies.

By late 1765, most stamp distributors had resigned, and legal and business proceedings only continued because the colonial legislatures threatened to withhold the salaries of those in a position to halt them. By the end of 1765, almost every colony was functional, without stamped paper.

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