Andrew Oliver discovered on August 14, 1765 that he had made a terrible career move – a decision that ultimately gave birth to the Liberty Tree of Boston, an important symbol of revolutionary fervor in the Massachusetts Colony.
When Parliament passed the Stamp Act in March of that 1765, Oliver, secretary to the province of Massachusetts and brother-in-law of future governor Thomas Hutchinson, won the appointment of tax stamp administrator for Massachusetts.

A 1774 British print depicts the tarring and feathering of Boston Commissioner of Customs John Malcolm in front of the Liberty Tree of Boston.
Though he did not favor the act personally, Oliver went along with the new job. The act required that documents, such as newspapers and contracts, bear the stamp showing taxes had been paid on them. This was something of an escalation of the disagreements between the colonies and the crown.
While England had long sought ways to make the colonies pay their own way, the Stamp Act would have teeth. Wills, contracts and other documents would have no legal weight if they were not written on paper that bore the official stamp. Being the administrator of the tax stamps would be a powerful and lucrative position.
The colonists had a long history of sliding around many of England’s trade rules that were designed to raise revenue, but the stamp act, colonists feared, would be hard to get around. No stamp and a contract could be ruled invalid. Making matters worse, the tax had to be paid in British Pounds Sterling.
Access to hard currency was always a problem in the colonies. And by refusing payments in either local currencies or other forms, the colonies could find themselves hard pressed to have enough British money available to meet their needs.
The Liberty Tree
Though the tax as proposed was relatively modest, the more forward thinking colonists realized the amounts could be raised at will once the precedent of a tax was established. And the merchants who were skilled at avoiding British laws realized that their skills could soon be rendered worthless.
These merchants in Boston were the early forerunners of the Sons of Liberty, and a group of them formed a political organization called “The Loyal Nine.” They set about fending off the Stamp Act. Their protests went public on August 14, 1765, when they hanged Andrew Oliver in effigy from a tree at the corner of Orange (now Washington) and Essex Streets.
On that day, the Liberty Tree was born. At first, the officials didn’t know exactly what to make of the protest. They debated responding and removing the dummy from the tree. But they concluded that taking action would provoke a response when the protest was meant to be peaceful. They were wrong.
The protesters had every intention of driving their point home. As the day wore on, they took the dummy down from the tree and proceeded to march to a building Oliver had constructed at his wharf. Believing that the structure was intended to be part of the Stamp Act enforcement, the group tore it down.
They then proceeded to Oliver’s home, where they burned the dummy and ransacked his offices. Oliver resigned. He told the Loyal Nine that he would not enforce the Stamp Act.
Death of Andrew Oliver
Similar tactics were employed elsewhere in the colonies, and soon the King found himself with no way to implement the tax. Though later repealed, it had set some important precedents. Among them: the establishment of the Liberty Tree as a rallying point for the Sons of Liberty and their followers.
It would serve its purpose for 10 years. Both the Patriots and the British troops used it as a scene for tar and feathering. The British used it to make their point when handing out punishments to the rebels.
The tree was a rallying point for patriots right up until its end, during the siege of Boston in 1775. In 1776, the British troops chopped it down in a show of defiance before they fled the city. Andrew Oliver, by then, was no longer around to care about the tree.
After his elevation to lieutenant governor when Hutchinson assumed the governorship in 1771, he died in 1774. The Sons of Liberty had grown much larger by that point, and were so boisterous that few of Oliver’s family dared attend his funeral for fear of attack.
This story last updated in 2022.