While the controversy from the writs died off, it did not take long for Britain to create a new controversy. In 1764, the British government imposed the Sugar Act, yet another in a long line of attempts to increase revenue for Britain. The act created new duties on Spanish wine and also significantly cut the duties on imported molasses that had been levied in 1733. To colonists, this signaled a change in Britain's attempts to tax the colonies. Prior to the Sugar Act, taxes had only been levied to regulate trade–never had they been specifically for a source of revenue. Adams was one of the only patriots to protest the act from the start; most others failed to recognize its importance.

The Sugar Act underscored a growing disconnect between Britain and the colonies. The French and Indian War had demonstrated that the colonies were unable to defend themselves with British troops, and thus the war had cost the homeland dearly; on the other hand, the influx of British troops and the need to provision and equip them had helped boost the economy in the colonies. Thus, the British argued that the colonies had gotten rich off the war while England shouldered the entire cost. Britain saw the taxes as an attempt to even the playing field and cover the costs of defending the colonies. The colonists saw things differently. With no voice in Parliament, many colonists saw the taxes as a burden without giving them any real opinion in how to spend it.

The disconnect only worsened when, in 1764, Britain proposed the Stamp Act–which would raise revenue through a special stamp placed on newspapers, legal documents, and commercial papers. Britain saw the Stamp Act as a progressive tax, in that it would be spread across all the colonies in proportion to each colony's wealth. The colonists, again, saw it differently. Since the working-class were most often involved in legal battles, the act hit them particularly hard and, thus, helped to rouse one of the most powerful demographic groups to oppose Britain. Colonists burned the Chancellor of the Exchequer in effigy and promised to hang him if he ever visited the colonies. Sons of Liberty clubs sprang up to oppose the tax, and they burned the stamps and drove out the stamp collectors. The Boston Sons of Liberty, headed by Sam Adams, were among the rowdiest patriots in the country. Adams seized this opportunity to restart his dreadful political career. In 1765, Adams was elected to the Massachusetts General Court.

At this point, though, Adams faced a more direct threat from the Massachusetts government: His accounts as tax collector were more than seven thousand pounds short. He had not embezzled the money, nor was he lax in his duties; he was, however, a terrible businessman. He had blown through his father's estate and, given time, would have likely bankrupted the city of Boston as well. However, he was so well liked that after his shortfalls were made public, Bostonians heartily reelected him to another term. The matter was soon lost in the growing brouhaha over the Stamp Act.

While Virginia led the political protest against the Stamp Act, Boston–under the leadership of Adams–chose a more direct route: The Sons of Liberty resolved to drive Andrew Oliver, Thomas Hutchinson's brother-in-law and the city's stamp master, out of the town. They hung Oliver in effigy from the city's Liberty Tree, and the Suffolk sheriff refused to cut it down out of fear for his life. On August 14, 1765, a mob (carefully constructed by Adams) destroyed a new building that was to be the stamp headquarters and then beheaded Oliver's effigy. After a bonfire on Fort Hill, the mob ransacked Oliver's house while the Governor watched helplessly nearby. When he asked for the town drummers to sound the alarm, a bystander told him the drummers were part of the mob. Oliver resigned his post the next day. Rumors swirled as the situation in Boston deteriorated. On August 28, another mob tore down the houses of several customs officers before leveling the house of Thomas Hutchinson.

Adams now set about trying to unite the various gangs that roamed Boston's streets–specifically those in North Boston with those in South Boston. When the two gangs marched side-by-side in the Pope's Day parade, it put Governor Bernard on alert that the gangs were no longer merely rabble, but the organized fighting force of Adams and the Sons of Liberty. Bernard retreated to Castle Williams, where the stamps had also been moved for safekeeping, and he wrote a plea to Britain for help against the "outright rebellion" brewing in Boston. The news shocked Britain, which still saw the stamp tax as fair and equitable and could not understand the colonists' refusal to yield. It would be three years still before British troops would arrive to enforce Parliament's taxes, and for the time being, Britain's lack of action signaled weakness to the colonies. Boston nearly had been given over to Adams and the Sons of Liberty, and they demanded that all business be conducted without stamps. They even forced Hutchinson from his post as probate judge.

In November 1765, the Stamp Act Congress convened in New York to make an effort to unite the colonies against the tax–all but four colonies attended. While little came of the congress, it helped lay the foundation for the later Continental Congress and allowed the Sons of Liberty to forge military alliances with other clubs in other colonies.

In 1766 Britain yielded to the colonial pressure and repealed the Stamp Act.

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