Pour the Oloroso sherry into a coupe. Swirl the glass around in the glass to coat the sides of the glass, then discard the liquid.
In an ice-filled cocktail shaker, combine the whiskey, lemon juice, Cynar and maple syrup. Shake vigorously, then strain into the coupe. Squeeze the orange peel over surface of the drink to release its oils, then drop the peel into the drink and serve.