Remove the piecrust from the refrigerator and place it in a 9-inch pie plate, allowing it to come to room temperature while you prepare the filling. This prevents the crust from cracking when it starts baking. While the crust settles, coarsely chop the pecans, measure out the chocolate chips, and combine the flour with the salt and espresso powder in a small bowl—this ensures even distribution of the espresso powder, which will add subtle depth without overpowering the filling.

In a medium saucepan over medium heat, combine the corn syrup, granulated sugar, and brown sugar. Bring the mixture to a gentle boil and let it bubble for exactly 5 minutes, stirring occasionally—this concentrates the syrup slightly and helps it bind with the eggs more effectively. While the syrup cooks, crack the eggs into a large bowl and whisk them together, then add the melted and cooled butter, bourbon, and vanilla extract, whisking until well combined.

Slowly pour the hot syrup into the egg mixture while whisking constantly—this tempering technique prevents the eggs from scrambling and creates a smooth, custard-like filling. Once combined, add the flour and salt mixture from Step 1, whisking until just incorporated and smooth. I find that working quickly but carefully here ensures the filling is perfectly emulsified before it hits the crust.

Scatter the chopped pecans and chocolate chips evenly across the bottom of the prepared piecrust. Pour the filling mixture from Step 3 carefully over the nuts and chocolate—they'll float slightly as the filling bakes, distributing throughout. Place the pie on a baking sheet (this catches any drips) and bake at 350°F for 45 to 50 minutes, until the filling is set around the edges but still has a slight jiggle in the very center when you gently shake the pan—this indicates the custard is perfectly cooked and will continue to set as it cools.

Remove the pie from the oven and let it cool on a wire rack at room temperature for at least 2 hours. I recommend cooling it completely before slicing—this allows the filling to set fully and makes clean slices possible. The pie can be served at room temperature or chilled; both temperatures showcase the bourbon and chocolate flavors beautifully.

Slice the cooled pie into wedges and serve each slice topped with a generous dollop of the whipped cream and a sprinkle of dark chocolate shavings. The cold cream contrasts wonderfully with the rich, warm spice of the bourbon filling.