08/14/2026
Colonial Tall Tales / The Day Boston Hung the Taxman
There are days in history when reasonable people sit down, discuss their differences, and attempt to reach a civilized solution ….. August 14, 1765, was not one of those days.
Boston was angry. Parliament had passed the Stamp Act, which meant colonists would soon be paying a tax on newspapers, legal documents, licenses and other printed materials. The colonists considered this completely unacceptable. So naturally, they hung the taxman from a tree … sort of.
Andrew Oliver had been appointed Massachusetts' distributor of the hated stamps. On the morning of August 14, Bostonians discovered an effigy of Oliver dangling from a large elm tree. Beside it were symbols warning everyone exactly what might happen to anyone foolish enough to help enforce the new tax. The message was subtle in roughly the same way a cannonball is subtle. Authorities ordered the effigy removed. Nobody seemed particularly interested in volunteering information.
As evening arrived, the crowd grew. Oliver's unfortunate likeness was cut down and paraded through the streets. Protestors descended upon a building associated with Oliver near the waterfront and tore it apart. Apparently, that wasn’t enough. The crowd moved on to Oliver's home. Windows were broken. Property was damaged. His carriage house was attacked.
And then, because every proper colonial uprising apparently requires refreshments, the crowd discovered Oliver's wine cellar.
By the following day, Andrew Oliver had gotten the message. He resigned as stamp distributor. The elm tree where his effigy had hung soon acquired a rather famous name: The Liberty Tree.
It became a gathering place for resistance to British rule, and August 14 itself would later be commemorated beneath its branches.
Ten years before Lexington and Concord, and eleven years before the Declaration of Independence, a group of very angry Bostonians had demonstrated something Britain was going to learn repeatedly: Americans could be remarkably difficult when somebody tried to tell them what to do ~ Especially when taxes were involved. And apparently... when there was wine in the basement.
Colonial Tall Tales — where history is occasionally so ridiculous we don't have to make anything up.