Combine whiskey,  lemon juice, and simple syrup in a cocktail shaker. Fill with ice, cover, and shake until outside of shaker is frosty, about 30 seconds. Strain into a glass filled with fresh ice. Gently pour 1/2 ounce fruity red wine (such as Shiraz or Malbec) over the back of a spoon held just above the drink’s surface so wine floats on top.