Add enough ice to the mixing glass to fill it. Stir briskly with a bar spoon for 20–30 seconds (about 30–40 full rotations) until the mixture is well chilled, slightly diluted, and the outside of the glass feels cold.

Prepare glass and strain

Discard ice/water from the chilled rocks glass if used. Place one large ice cube into the rocks glass. Strain the mixed cocktail over the large ice cube using a Hawthorne or julep strainer.

Finish with express and garnish

Hold an orange peel over the drink and give it a firm squeeze to express oils over the surface, then rub the peel around the rim and drop it into the glass. Skewer or drop one Luxardo or maraschino cherry into the drink.

Serve

Present immediately. Recommend tasting note: rich bourbon backbone brightened by nutty, savory sherry and rounded by demerara sweetness with aromatic bitters and orange oils.

Optional / Tools

If you don't have demerara syrup, make simple demerara syrup by combining 2 parts demerara sugar and 1 part hot water, stirring until dissolved, then cooling before use.

To make a large ice cube: fill a silicone cube mold with water and freeze slowly (insulated cooler method) to minimize cloudiness and ensure a clear cube that chills more slowly.