Drain pineapple, reserving juice in a 2-cup measuring cup. Set pineapple aside. Add enough water to juice to measure 1-1/2 cups; transfer to a saucepan. Whisk in the pudding mix and gelatin until combined. Bring to a boil; cook and stir for 1-2 minutes or until thickened. Stir in pineapple. Remove from the heat; cool for 10 minutes.
Add the strawberries; toss gently to coat. Pour into crust. Refrigerate until set, about 3 hours. Garnish each piece with 1 tablespoon whipped topping. Refrigerate leftovers.