Gather all the necessary ingredients for the cocktail. Make sure your whiskey, lemon juice, simple syrup, and red wine are all ready to use.
Take a cocktail shaker and fill it with ice cubes. This will chill the ingredients as you mix them together and help dilute the drink slightly.
Measure out 2 ounces of bourbon or rye whiskey and pour it into the cocktail shaker over the ice.
Measure out 3/4 ounces of fresh lemon juice and add it to the shaker with the whiskey and ice.
Measure out 1/2 ounce of simple syrup and pour it into the shaker along with the other ingredients. The simple syrup will balance out the tartness of the lemon juice.
Secure the lid on the cocktail shaker and shake vigorously for about 10-15 seconds. This will thoroughly mix the ingredients and chill the drink.
Place a strainer over a rocks glass filled with fresh ice cubes. Carefully pour the contents of the shaker through the strainer and into the glass. This will remove any ice chips or pulp from the lemon juice, giving you a smooth cocktail.
Slowly pour 1/2 ounce of red wine over the back of a spoon held just above the surface of the drink. This will create a distinct layer of wine on top of the cocktail. The red wine should float on the surface, creating a visually appealing presentation.