Drizzle a very small amount of Sambuca into the bottom of a double rocks glass and twist the glass all around to wash the whole inside of the glass with the Sambuca.
In an ice filled Boston cocktail shaker, combine whiskey, triple sec, simple syrup and shake for 10-15 seconds. Put 1-2 large square cubes of ice (approx 1.5") in the double rocks glass and pour the contents of the Boston cocktail shaker with the large ice cubes inside the double rocks glass.
Add 3 dashes of bitters on top. Garnish with sliced orange peel approximately 1.5" long by 0.5" wide and add a cherry.