1 teaspoon
crushed red pepper flakes, plus more for serving
½ teaspoon
freshly cracked black pepper
½ cup
Castelvetrano olives
Method
Preheat the oven to 400°F with a rack in the center position.
Season the chicken all over with 2 teaspoons of the salt.
Heat the olive oil in a large oven proof skillet over medium-high heat. Once the oil is glistening, add the chicken, skin sides down, and cook until golden brown, about 5 minutes, then flip and cook until browned, about 3 minutes more. Transfer the chicken to a plate.
Add the oranges to the skillet in a single layer and cook until softened and the rinds begin to brown, 2 to 3 minutes. Flip the orange slices, then add the vinegar, olive brine, bay leaf, garlic, red pepper flakes, and remaining ½ teaspoon of salt. Arrange the chicken on top of the oranges, pouring over any collected juices. Bake for about 30 minutes, or until the skin is golden brown and the internal temperature of the chicken reads 165°F on an instant-read thermometer. Remove from the oven. Using a spoon, baste the chicken with the sauce. Top with black pepper and olives and return to the oven for another 10 minutes, or until the olives are warmed through.
Transfer the chicken, oranges, and olives to a large platter and pour the sauce over top. Top with more red pepper flakes, if desired, and serve immediately.