This ultra-hearty chicken dish is the perfect balance of warm earthy flavors and tangy, salty toppings. If you prefer, you can subsitute any citrus of your choosing in place of the grapefruit. If you can't get your hands on Castelvetrano olives, you can substitute for a different olive, but we highly recommend giving this buttery, beautifully green variety a try if possible. This dish is best eaten immediately, as that crispy skin won't stay crisp forever.
Pat chicken dry with paper towels. Sprinkle chicken evenly with salt and let stand in the refrigerator for at least 30 minutes (or up to overnight). Bring chicken back to room temperature before cooking.
Preheat oven to 425°.
Rub skin side of the chicken thighs evenly with 1 tablespoon olive oil. Place thighs, skin side down, in a single layer in a medium cast-iron skillet over medium heat. Let fat render for about 5 minutes, then increase heat to medium-high. Cook until skin is golden brown and beginning to crisp, another 8 minutes (do not move chicken until the edges start to turn golden). Turn thighs over and cook other side for about 3 minutes; transfer to a plate.
Add the grapefruit slices, zest, and rosemary to the cast-iron skillet, and cook until citrus is caramelized, about 3 minutes on each side. Return thighs to the pan, skin side down and transfer to oven. Bake at 425° for 5 minutes, or until a thermometer inserted in thickest part of chicken thigh reads at least 170 °.
Toast walnuts in a small skillet over medium heat until golden brown and fragrant, about 6-8 minutes. Combine walnuts, olives, feta, vinegar, and remaining 2 tablespoons olive oil in a bowl. Top chicken with walnut mixture and serve immediately.
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