In a mixing glass, add ice, bourbon whiskey, fig simple syrup, and 2 dashes of Angostura bitters.
Stir for about 15–20 seconds.
Strain the mixture into an old-fashioned glass with an ice ball.
Garnish with a fresh fig.
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Notes
Is it possible to substitute fresh figs for fig syrup?Definitely! Before adding the remaining ingredients, muddle a few fresh figs in the mixing glass to release their flavor.Would it be acceptable to use a different kind of whiskey?Bourbon is classic, but rye and even light Scotch can be good substitutes; try different ones until you find one you like.What is the best way to prepare fig syrup?When the sugar has dissolved and the mixture has thickened, add a few fresh figs and simmer the combination with equal parts water and sugar. Before using, strain and allow to cool.
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