1. Prepare your orange segments and place into the bottom of an empty cocktail shaker, add 6-8 fresh basil leaves that have been torn, add in citrus simple, and gently muddle with a flat head, wooden muddler.
2. Add ice and bourbon. Shake until frost forms on the outside of the shaker.
3. Strain pour over ice into a footed rocks glass.
4. Garnish with an orange slice and basil leaves.

For the citrus simple syrup:

1. Add water and sugar to small saucepot and bring to a boil. Reduce heat to a low simmer.
2. Zest the lemon and the orange and add zest into pot.
3. Squeeze juice of lemon and orange, add into pot and stir until mixed. Simmer on low for 20 minutes.
4. Remove from heat and add into an airtight jar. Add zested and squeezed citrus.
5. Let the mixture come to room temperature and store it in the refrigerator. Keeps for about a month.