Make the pie dough. Combine 2 ¼ cups flour, 2 tsp sugar, and ½ tsp Kosher salt in the bowl of a food processor fitted with blade attachment. Pulse to blend, then add 8 Tbsp (1 stick) cold butter and 7 Tbsp shortening. Pulse until small pea-sized pieces forms. Add 5 Tbsp ice water, then pulse until dough just begins to hold together.
Chill the pie dough. Transfer to a lightly floured surface, pat into a round disk, then wrap in plastic wrap. Place in refrigerator for 30 minutes.
Prepare the filling. Whisk together 3 large eggs, ⅔ cup brown sugar, ⅔ cup corn syrup, 3 Tbsp bourbon, 2 Tbsp melted butter, 1 tsp vanilla extract, and 1 tsp Kosher salt in a large mixing bowl. Add 2 cups chopped pecans and ¾ cup chocolate chips, then stir to combine. Set aside.
Roll out the pie dough. Preheat oven to 350 F. Roll dough out on a lightly floured surface into a 12” round. Carefully transfer dough to pie dish. Fold excess dough under the edges, then decoratively crimp with fingers or tines on a fork.
Add the chocolate bourbon filling. Pour filling into pie dough -- add a few whole peans right on top, if desired -- then transfer to a baking sheet. Bake for 55-60 minutes, or until edges are golden brown and the center of the pie is set. Let pie cool for at least an hour before slicing into it.
Make the cinnamon whipped cream. Pour 1 cup heavy cream into the bowl of a stand mixer fitted with whisk attachment. Whisk on medium-high speed until peaks start to form, about 3 minutes, then add 2 Tbsp confectioner’s sugar, 1 tsp vanilla extract, and1 tsp ground cinnamon. Continue whisking until cream is fully whipped and reached desired consistency. Serve immediately.