Make simple syrup by heating water and granulated sugar of medium heat until all sugar has dissolved. Remove from heat, add pomegranate seeds, and allow to cool completely. Run through blender and then strain through fine mesh strainer. Discard seed solid and keep the pink syrup.
To make the cocktail, combine bourbon whiskey, lemon juice, and pomegranate simple syrup in a shaker with ice. Vigorously shake until well combined, about 20 seconds. Strain into a low ball ice with extra large ice cubes.
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