Soak the raisins in rum for 10 minutes to plump them up. Fold together the vanilla pudding, sugar and whipped heavy cream. Cut the cooled cinnamon toast bread pudding into large cubes, about 1 1/2-inches. Layer half the bread pudding cubes into the bottom of a large trifle dish or serving bowl and sprinkle with raisins. Spoon half the cinnamon pudding over the raisins and bread pudding. Sprinkle half of the rum raisins on top. Repeat the layers with remaining ingredients. Chill in the refrigerator for 4 hours before serving. Serve with sweetened whipped cream, if desired.
Cinnamon Toast Bread Pudding
Preheat oven to 350 degrees F. Butter a 9 by 13-inch baking dish.
Arrange the cinnamon toast, in shingled rows, in the prepared baking dish. In a large mixing bowl, whisk eggs, brown sugar, cream, milk and vanilla together. Pour the egg mixture over the cinnamon toast. Cover and refrigerate for 1 hour, pressing down on the cinnamon toast occasionally into the egg mixture. Bake for 1 hour until puffed and golden.