For the Strawberry Pudding: Set a medium saucepot on the stovetop, and pull out a blender. In the blender, combine the strawberries in their syrup, milk, cream cheese, sugar, cornstarch, vanilla extract, and salt. Cover and puree until very smooth. Then pour the mixture in the saucepot.
Simmer the strawberry pudding over medium heat, stirring consistently until the mixture is smooth and thick. Remove from heat. (Note: The pudding will thicken more as it cools, so don't let it cook too long. 5-6 minutes at the most.)
For Assembly: You will need 15 small whole strawberries or 15 large strawberry halves for the garnish. If needed cut large strawberries in half.
Pull out a 9X13 inch baking dish. Arrange one bag of Chessmen cookies in a single layer on the bottom of the baking dish.
Scoop the strawberry pudding over the Chessmen cookies. Spread it out into an even layer. Arrange the second bag of Chessmen cookies over the top of the pudding.
For the Whipped Cream: In a stand mixer, combine cold heavy cream and sugar. Using the whip attachment, whip the cream on high until firm.
Once the pudding has cooled 5-10 minutes, spread the whipped cream over the top of the cookies. Top the whipped cream with 15 strawberries. Chill for 1-2 hours before serving. The pudding should be firm enough to cut and lift out of the pan, supported by the cookies.
Make Ahead: You can make this Homemade Pudding Recipe up to 4 days in advance. Wrap and chill until ready to use.