Heat 1 tablespoon of oil in a large skillet over medium heat. Add leek and apple and saute 4 minutes, until tender and golden. Add oregano, rosemary, and salt and pepper, to taste, and stir to coat. Transfer mixture to a large bowl and add bread cubes and chicken broth. Mix well and set aside.
Using a sharp knife, slice pockets into chops by slicing horizontally into the side, and almost through to the other side. Season the outside with salt and pepper. Stuff chops with apple mixture, allowing stuffing to overflow out of pockets.
Heat remaining oil in a large skillet over medium-high heat. Add pork chops and sear on 1 side until browned, 3 to 4 minutes. Flip chops and transfer to oven to finish cooking for 8 to 10 minutes, or until cooked through.