In a small bowl, drain cherry juice and add rum; set aside. Prepare vanilla and chocolate puddings in separate bowls, according to package directions. Allow to set up 5 minutes.
In a 9×13 inch baking dish or trifle bowl, place a layer of cookies on the bottom of the dish; cut a few of the cookies in order to create a tight fit, if needed.
Sprinkle cookie layer with 1/3 of the cherry juice mixture and spoon vanilla pudding over the cookies, spreading to the edge of the pan. Repeat steps with cookies, cherry juice and chocolate pudding. Make final layer with cookies and remaining juice.
In a medium bowl, whip cream and sugar together until soft peaks form. Top dessert with whipped cream, sprinkle with almonds, and garnish with whole cherries. Refrigerate for 2 hours or more before serving.