Preheat the oven to 350°. Line a baking sheet with tin foil and lightly spray with vegetable spray. Set aside.
Make the glaze
In a small bowl combine the brown sugar, worcestershire, dijon mustard, ketchup and bourbon and stir to combine. Set aside.
In a small bowl, combine the bread and milk -- soak for 5 minutes. Meanwhile, in a small skillet, heat the olive oil over medium heat. Add the onions and saute until softened and slightly translucent, about 4-5 minutes, set aside to cool while you assemble the rest of the ingredients.
In a large bowl combine the eggs, parsley, steak seasoning, worcestershire sauce and whisk together to combine. Add the bread and the onions and stir until well incorporated. Add the ground pork and ground chuck and fold the wet ingredients into the meat with your hands. Don't overwork the meat -- just continue to gently fold until the wet ingredients are completely incorporated. Transfer the meat to the baking sheet and mold it into a loaf shape. Spread half of the sauce over the meatloaf and bake for 45 minutes. Remove the meatloaf and spread the rest of the glaze over the meatloaf. Return to the oven and continue baking for 20-25 minutes. Let the meatloaf rest for 5-10 minutes before slicing.