At the time of the Whiskey Rebellion, there were only 3 banks in the entire country, and they were in New York and Philadelphia. Money did not circulate on the frontier.
The US had not yet begun minting our first coins of gold, silver and base metals. Some states had minted coins, but most money circulating in the cities was gold and silver of British, French or Spanish manufacture. The newer coins had known values. Older coins had been clipped so many times that a merchant would weigh the coins to assign a value before accepting them.
On the frontier it was worse, and there was an established barter system in place based on alcohol. The smallholders of Kentucky or western Pennsylvania preserved the value of their orchards and fields by fermenting the products thereof. A barrel of beer, ale, stout or porter -- or a cask of brandy or whiskey -- had a known value when bartered for a side of bacon or a barrel of flour.
The tax on whiskey rankled because it struck right at the financial core of frontier life: There was no money in the sense we know it. It reminded people too much of the British "revenooers" who knocked down doors to collect taxes for King George, and people had just fought a war for economic self-determination so as to put an end to all that. Hamilton and Washington picked western Pennsylvania for a test case because, had they picked Kentucky, the secession question would have opened up a whole lot sooner. The fix was in as far as western Pennsylvania was concerned.
The tax on whiskey showed questionable judgment.
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