Preheat your oven to 400°F (200°C).
Sprinkle salt and pepper evenly over both sides of each pork chop.
In a small bowl, combine onion powder, garlic powder, Italian seasoning, and brown sugar. Mix the ingredients well.
Wrap each well-seasoned pork chop with 2-3 uncooked bacon slices. You might need to secure the bacon slices with toothpicks to keep them in place.
Sprinkle the brown sugar mixture evenly over all sides of the wrapped pork chops.
Line a rimmed baking sheet with parchment paper or aluminum foil, then place a wire rack on top of the lined baking sheet.
Place the bacon-wrapped pork chops on the wire rack, leaving space between each chop.
Bake the wrapped pork chops in the preheated oven for 25-30 minutes. I recommend using an instant-read thermometer to check that the internal temperature of the thickest part of the meat reaches 145°F (63°C).
Remove the juicy pork chops from the oven and let them rest for 3-5 minutes before serving with asparagus, Brussels sprouts, green beans, potatoes, or a salad.