Combine the sugar and water in a small saucepan and bring to a boil, stirring until the sugar is dissolved. Lower the heat and simmer for 5 minutes. Turn off the heat and let the simple syrup cool to room temperature.
Muddle half of the maraschino cherries and orange slices with the simple syrup in a cocktail shaker. Add the bourbon and lemon juice. Fill the shaker halfway with ice and shake well. Strain into four rocks glasses filled with ice. Garnish each glass with a maraschino and an orange slice.