Add the pepper to a small saucepan with the maraschino cherry juice. Bring to a boil and reduce for 2 minutes. Remove from the heat, strain and cool.
In a shaker add the orange supremes and a little of the reserved orange juice (reserving 4 supremes for garnish), and muddle together. Add 1/4 cup of the black pepper cherry syrup, the bourbon and a scoop of ice. Shake and pour into 4 rocks glasses with a big ice cube in each. Garnish each drink with an orange supreme and a maraschino cherry.