Clean and dice the strawberries. Pour the sugar over the strawberries and stir to coat. Set aside.
In a large bowl add both the cheesecake pudding packages together and the milk and mix together on low speed until mixture thickens. Place in the refrigerator to chill for 5 to 10 minutes or until set.
Place a vanilla wafer in the bottom of a pint-size glass jar and top with a layer of cheesecake pudding, followed by another vanilla wafer.
Next add a layer of strawberries and another vanilla wafer.
Then add a layer of cool whip, a layer of strawberries, and another vanilla wafer. And final layer add cheesecake pudding, another vanilla wafer, and then cool whip.
Top with a whole strawberry and a vanilla wafer.
Cover with plastic wrap and store in the refrigerator until ready to eat.