Heat one tablespoon of olive oil in a large, ovenproof skillet or sauté pan over medium-high heat. Add diced onion and garlic and cook for 4-5 minutes, stirring occasionally, until the onion is soft and fragrant.
Reduce heat to medium and add another tablespoon of olive oil. Add the kale, apple, cinnamon, lemon zest, and fresh rosemary to the skillet and cook for 3-4 minutes, stirring occasionally, until the apple is soft and the kale is just wilted.
Season with salt and black pepper, to taste, and stir to combine. Remove from heat and transfer apple mixture to a medium-sized bowl and set aside.
With a sharp knife, carefully make a slit through the center of each pork chop to form a pocket. Do not cut all the way through. Divide the apple-rosemary filling between the 4 pork chops and secure the openings with toothpicks to hold the stuffing inside.
Return the skillet to medium-high heat and add the remaining olive oil. Sear the pork chops on both sides until golden brown, around 3-4 minutes per side. Season with additional salt and black pepper, if desired.
Transfer the skillet with the pork chops to the preheated oven and roast for 15-20 minutes or until the pork chops are cooked through, around 15-20 minutes or until an instant-read thermometer inserted in the center reads 145°F (63C).
Allow the pork chops to rest for 3-5 minutes before serving with Garlic and Chive Cauliflower Mash or your favorite side dish. Enjoy!