This dessert is a tribute to Jude’s early life in Boston and represents the sweetness and bitterness of his past, much like the layers of the pie itself.
Preheat oven to 350°F.
Cream butter and sugar together until light and fluffy.
Add eggs one at a time, then vanilla.
Alternately add flour and milk, mixing until smooth.
Pour into a greased cake pan and bake for 25 minutes.
For the filling, heat heavy cream until just boiling, then pour over chocolate chips and stir until smooth.
Cool, then layer between cake halves.