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Place the sugar cube in a lowball glass and add the bitters. Add the water and mash and swirl it with a muddler or wooden spoon until the sugar is mostly dissolved.
Add the bourbon whiskey and swirl to combine. Add a large ice cube.
Use a knife to remove a 1″ wide strip of the orange peel. Squeeze the orange peel into the drink to release the oils. Gently run the peel around the edge of the glass, then place it in the glass. If desired, garnish with a cocktail cherry for additional sweetness.