Using a food processor (or a gallon size ziploc), crush the Oreos. Set aside.
For the cheesecake filling - in the bowl of a stand mixer, combine the softened cream cheese, vanilla extract, salt, cocoa and powdered sugar.
Mix on low speed until thoroughly combined, scraping the sides down often.
Add in the Baileys and mix on low just until combined. Bump up the speed and mix on medium for an additional minute or until smooth and thoroughly combined. Scrape the sides often.
Transfer the cheesecake filling to a piping bag, set aside.
For the whipped topping - in the bowl of a stand mixer, whip the heavy whipping cream on medium until soft peaks.
Add in the powdered sugar, cocoa and Baileys. Mix on low until combined and then bump up the speed and mix on medium until stiff peaks.
Transfer the whipped topping to a piping bag fitted with a large star tip, set aside.
To assemble, use a tablespoon to scoop one spoonful of crushed Oreos into the bottom of each trifle container.
Top with a layer of the cheesecake filling.
Top with a layer of the whipped topping.
Repeat another layer of crushed Oreos.
Repeat another layer of the cheesecake filling.
Pipe a mound of the whipped topping.
Finally, sprinkle with the remaining crushed Oreo pieces.