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This drink is often mixed in the glass in which it is to be served. Shaking better incorporates the flavours produced by muddling and fine straining removes...
I make them muddled for guests that do not like straight bourbon. I gently muddle a cherry in the serving glass, add syrup, bitters and stir. Add a shot of bourbon and ice, stir. I may stop here and serve if they do not want it too strong. Otherwise I had a half shot or so of rye whiskey (or more bourbon). Orange peel squeezed and then rubbed on the rim. Garnish with the orange peel and another cherry. I only muddle orange when requested, and then I prepare outside of the serving glass.