Make the pudding base: In a large mixing bowl, combine both cans of crushed pineapple with their juices along with the coconut cream pudding mix. Stir well until the pudding powder is fully dissolved and the mixture is smooth.
Incorporate the condensed milk: Add the sweetened condensed milk and mix thoroughly to blend all ingredients evenly.
Fold in extras: Carefully fold in the drained maraschino cherries, toasted macadamia nuts, mini marshmallows, and thawed whipped topping until all components are evenly mixed.
Chill: Cover the bowl with plastic wrap and refrigerate for at least two hours, allowing the dessert to set and chill completely.
Serve: Just before serving, optionally top with extra whipped cream, maraschino cherries, and toasted macadamia nuts for a beautiful presentation. Enjoy chilled!