In a large mixing bowl, cream together the softened butter, brown sugar, and vanilla extract until light and fluffy.
Add the crushed graham crackers, kosher salt, and milk to the mixture, stirring until well combined.
Gently fold in the mini chocolate chips until evenly distributed throughout the cookie dough.
In a separate bowl, prepare the chocolate pudding by whisking together the instant pudding mix and cold milk until smooth. Set aside.
In another bowl, fold the mini chocolate chips into the thawed whipped cream to create the chocolate chip whipped cream. Set aside.
To assemble the trifle, start by placing a layer of cookie dough at the bottom of a trifle dish.
Add a layer of chocolate pudding on top of the cookie dough, followed by a layer of chocolate chip whipped cream.
Repeat the layers until all ingredients are used up, finishing with a layer of whipped cream on top.
Garnish the trifle with additional mini chocolate chips and crumbled chocolate chip cookies.
Chill the trifle in the refrigerator for at least 2 hours before serving to allow the flavors to meld together.