Finely crumble gingerbread onto a plate. Quarter lemon and rub halfway around the edge of the serving glass. Roll lemon-coated side through the crumbled gingerbread, then set the glass aside. Add Irish whiskey, lemon juice, and gingerbread syrup to a cocktail shaker. Fill with ice and shake vigorously.
Strain the drink into the prepared cocktail glass filled with ice. Fill up with ginger ale.
Gently pour red wine over the back of a spoon into the drink so it floats on top. Enjoy!