What's up with the E in Whisky?
According to Master of Malt (see source here), the difference in spelling originated from the desire of 19th century Irish distillers to differentiate their Whiskey from that produced in Scotland which was deemed a poor quality Whisky. Ireland, having been distilling Whisky way before Scotland, wanted to set itself apart from people they considered copycats. This differentiation was then carried over into the countries that Scotland and Ireland influenced and that is where the difference in spelling started. The argument goes that if the country learned or traces their distilling heritage to Scotland then they will use Whisky but if they trace their heritage to Ireland they will use Whiskey.
The United State of America is a big producer of Whiskey in the world and it adopted the Irish spelling due mainly to the fact that Whiskey distilling in the USA was introduced by Irish missionaries. With this skills transfer also came the adoption of the Irish spelling for Whiskey. American Whiskey may have started off as an Irish varietal but over time, Whiskey in America evolved to become its own unique product called Bourbon but it kept the Irish spelling for Whiskey. Keep in mind though that not all American distilleries today adopt the Irish spelling (see Maker's Mark, Rittenhouse, George Dickel) mainly due to some brands having a Scottish heritage instead of Irish heritage.

In summary, the difference in the spelling started as a dick move by Ireland in trying to differentiate its Irish Whiskey from Scotch Whisky. This difference in spelling was then carried over to countries each distilling culture influenced through out history. Although the countries they influenced ended up making their own unique Whiskies the influence in the spelling remains.
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