If cornbread is fresh, cube and toast lightly in a 350°F (175°C) oven 6–8 minutes until slightly dry and golden. Place crumbled/toasted cornbread in a medium saucepan.

Add liquids and simmer

Add water, granulated sugar, unsalted butter, and a pinch of salt to the saucepan with the cornbread. Bring to a gentle simmer over medium heat, stirring to dissolve sugar and melt butter. Reduce heat to low and simmer very gently, mashing the cornbread with a spoon, for 10–12 minutes to extract flavor.

Strain and finish

Remove from heat and let steep 5 minutes. Strain the mixture through a fine-mesh sieve or cheesecloth into a bowl, pressing to extract liquid (discard solids). Stir in vanilla extract. Cool to room temperature, then refrigerate. This yields approximately 200–300 ml thick syrup. Adjust sweetness by adding a little extra water if too thick or sweet.

Cocktail Assembly

Chill: Place an Old Fashioned glass in the freezer or add a large ice cube to chill briefly.

Measure and combine: In a mixing glass or cocktail shaker filled with ice, add 4 tbs (approx. 60 ml) Elijah Craig Small Batch bourbon, 30 ml cornbread syrup, 15 ml fresh orange juice, 3 tsp chocolate bitters, and 1 tsp Angostura bitters.

Stir: Stir the mixture for 20–30 seconds until well chilled and slightly diluted (about 12–15 turns with a bar spoon). The goal is to integrate the cornbread syrup and balance alcohol.

Strain: Strain the cocktail into the chilled Old Fashioned glass over one large ice cube (or a few small cubes).

Garnish and finish: Express an orange twist over the drink to release oils, rub the rim with the twist, and drop it in. Optionally sprinkle 1 tbs crumbled toasted cornbread on top for aroma and visual texture. Serve immediately.