In a food processor, puree pineapple until like a sauce.
Place one cup pineapple puree into the blender. Reserve a one tablespoon for topping.
Pour in a half a cup heavy whipping cream, two tablespoons simple syrup, and three cups ice. Blend well until thick. If too thick add a little more heavy cream. It's supposed to be thick.
Pour mixture into a cup and top with whipped topping and pineapple puree.