Add chai syrup and bitters to mixing glass and stir to combine.
Fill the glass with ice then pour in bourbon and stir until chilled to the touch (about eight seconds).
Strain the liquid into a rocks glass over large ice cube.
Peel off a strip of orange rind and squeeze it over top of the cocktail to express its oils then drop the peel into the glass for garnish.
Garnish with star anise, if desired.
Notes
Making the Chai Syrup
In a small saucepan, dissolve 2 cups of brown sugar, 1 ½ tablespoon ground ginger, 3 teaspoon ground cinnamon, 2 teaspoon ground allspice, 1 ½ teaspoon ground clove, 1 ½ teaspoon ground cardamom, 1 ½ teaspoon ground black pepper, and 1 teaspoon ground nutmeg in 1 ¾ cup water over medium heat on stove top.
Bring the mixture to a boil then reduce heat to low and simmer for 10 minutes.
Remove from heat and cool fully before using in cocktails. Makes 24 servings.
PreparationYou can mix this drink up to two days in advance then store in the fridge or freezer. I recommend reserving the ice until serving and giving the cocktail a good stir or shake as some separation may occur.To large batch the cocktail, combine two ounces of chai syrup with 8-12 dashes of bitters. Add ice then six ounces of bourbon and stir until chilled. Divide the mixture between four rocks glasses over fresh ice chunks the express orange oil over each. Serves four.Cocktail Tool SubstitutionsInstead of a cocktail mixing glass and a bar spoon you can use a highball glass and a regular table spoon or butter knife.If you don't have a jigger to measure the liquor with, a standard size shot glass is a great substitute that holds about the same amount of liquid as the large end of a jigger.Don't have a cocktail strainer? Use another glass to cover all but a sliver of the mixing glass as you pour so that just the liquid comes out. A mesh strainer also works well.