Chill Glass: Choose an old fashioned glass, ice it up, stir and set aside.
Prep Shaker: Place 3 orange slices and 2 lemon slices in your shaker.
Muddle: Use a muddler to crush the fruit and release their juices.
Add Simple Syrup: Measure and pour ½ oz simple syrup into the shaker.
Add Bourbon: Pour 2 oz Bourbon into the shaker.
Add Ice: Fill your shaker with ice cubes.
Shake: Close the shaker and give it a good shake to mix all the ingredients.
Prep Glass: Discard the ice from your old fashioned glass.
Serve: Strain the mixture into the glass and fill the glass with crushed ice.
Garnish: Put a straw into the glass and place a sprig of mint on top for garnish.