In a bowl, whisk together the brown sugar, soy sauce, pineapple juice, onion powder, garlic powder, ginger, black pepper, apple cider vinegar, and red pepper flakes until the sugar dissolves completely. This creates a well-balanced marinade with sweet, savory, and spiced layers that will penetrate the pork beautifully.

Pat the pork chops dry with paper towels and use a fork to poke small holes all over both sides—this helps the marinade penetrate deeper into the meat. Place the pork chops in a shallow dish or resealable bag and pour the marinade from Step 1 over them, ensuring they're fully coated. Refrigerate for at least 6 hours, or ideally overnight, for maximum flavor development. I find that marinating overnight gives the pork a much more complex, seasoned interior.

Preheat your grill to medium-high heat (around 400°F) for about 10-15 minutes. Remove the pork chops from the refrigerator about 15 minutes before grilling to bring them closer to room temperature for more even cooking. Drain the pineapple slices and set them aside for grilling. Lightly brush the grill grates with oil to prevent sticking.

Place the marinated pork chops directly on the grill grates and cook for 4 minutes on the first side without moving them—this creates a nice caramelized crust. Flip and cook for another 4 minutes on the second side until the internal temperature reaches 145°F. During the last 2-3 minutes of cooking, place the pineapple slices on the grill and cook until they develop golden-brown char marks on both sides, about 1-2 minutes per side. I like to reserve some of the marinade to brush on the pineapple while it grills for extra flavor.

Transfer the grilled pork chops to a serving platter. Top each pork chop with a grilled pineapple slice and sprinkle with freshly chopped parsley for a fresh, bright finish. Serve immediately while the pork is still warm and juicy.