Preheat the oven to 350 degrees. Spray 3 - 6” cake pans with nonstick cooking spray containing flour and set aside.
In a large bowl, use an electric mixer to beat the sugar and butter together until it has lightened in color, about 2-3 minutes.
Add in the eggs, one at a time, beating each time thoroughly to combine each egg before adding the next.
Add the vanilla with the last egg and beat until the mixture is light and fluffy.
Alternate adding the flour and the milk, beginning and ending with the flour, adding the baking powder and salt with one of the flour additions.
Add the crushed cookies and use a spatula to fold the cookies into the batter.
Divide the batter evenly between the 3 baking pans (a kitchen scale can be handy).
Place the pans in the oven and bake for 30-32 minutes, or until a toothpick comes out cleanly.
Let the cake cool in their pans for about 10 minutes before turning them out onto a cooling rack to come to room temperature.
To make the frosting, place the butter in a large bowl and beat with an electric mixer until the color has lightened, about 2-3 minutes.
Add in the powdered sugar and vanilla and continue to mix. If the frosting is too stiff, start by adding 2 tablespoons of heavy cream until it has loosened (adding more if needed).
In a food processor, place the cookies (again–no filling, just the cookie) and pulse until the cookies have turned into fine crumbs, taking care there are no large pieces.
Transfer about 1 cup of frosting into a smaller bowl and add ½ c of the crumbs to the smaller bowl of frosting and mix. This frosting will be used in between the layers of cake only.
To assemble the cake, start by placing the first layer of cake on a cake plate/pedestal with the flat side down.
Scoop about ½ c of cookie frosting and spread it in an even layer over the top of the cake.
Take the next layer and place it with the flat side up.
Scoop about ½ c of the cookie frosting and spread it in an even layer over the top of the cake.
Place the top layer of cake with the flat side up.
Scoop the remaining plain frosting onto the top and sides and spread it in an even layer.
To make the ganache, heat the heavy cream in a microwave safe container just until it’s simmering.
Remove and pour over the white chocolate chips and let them sit for 2 minutes.
Use a small whisk and stir the chocolate until it’s smooth and there aren’t any lumps.
Let the ganache cool enough that it is pourable, but not too hot to melt the frosting.
Pour the ganache over the top of the cake and let it drip down the sides of the cake as desired.
Sprinkle the remaining cookie crumbs into the ganache before it sets.
Slice and enjoy!