Preheat the oven to 400°F. Place the cast iron skillet in the oven to heat with it and heat for 30 minutes.
Combine the paprika, oregano, garlic, salt, pepper, and parsley in a bowl. Coat the chicken in it and wrap the bacon around the thighs. You will need 1-2 slices per thigh depending on the size.
Remove the cast iron from the pan and place each of the bacon wrapped chicken thighs into the pan. Sprinkle with the brown sugar and place back in the oven. Bake for 30 minutes or until the internal temperature of the chicken reaches 165 degrees
Heat the broiler and place the pan as close to it as possible. Cook for an extra 1-2 minutes or until the brown sugar and bacon and crisped.