Adapted from a recipe by Bob Perry, executive chef of My Old Kentucky Dinner Train, Bardstown, Kentucky
In a heavy saucepan set over medium-high heat, combine sugar and water and bring to a boil. Cook, washing down the sides of the pan with a moistened pastry brush, until the temperature reaches 222F on a candy thermometer. (Work carefully; hot sugar can cause a nasty burn.) Remove pan from heat.
Mix orange juice and Bourbon and pour into sugar. Stir well. Mix in cherries, remove from heat and let them plump for 20 minutes. The sauce may be rewarmed.
Meanwhile, using a sharp knife, score skin and fat of duck breasts in a checkerboard pattern. Season with salt and pepper to taste, and coat lightly with a bit of olive oil. Heat a large skillet over medium-high heat. Place breasts into pan in a single layer, skin-side down. Sear until golden, 2 to 3 minutes. Turn and sear on the other side, 2 to 3 minutes. Remove from heat and let rest for 5 minutes.
To serve, slice each duck breast half in medallions and fan slices out on serving plate. Drizzle sauce over slices and decoratively around each plate.