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Peel and cut butternut squash, place on parchment covered cookie sheet and drizzle with olive oil and sprinkle with sea salt and pepper. Toss. Place in upper third of oven.
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Season both sides of chicken with sea salt, pepper and powdered garlic, dredge chicken in flour of your choice, set aside.
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Place a cast iron skillet on cooktop on med/high heat. Add butter or olive oil. Use enough so bottom of skillet is well coated.
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When butter is melted and pan is hot, add chicken skin side down to pan. You want to hear a pshhhhhh sound.
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Cook for six minutes or until chicken is nicely browned.
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Add shallots to skillet.
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Place in oven (on lower rack if you have a single oven, upper rack if you have a double oven). Set timer for 30 minutes.
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When timer goes off, turn chicken skin side up (and if using a single oven place skillet on upper rack moving butternut squash to the lower rack.) Set timer for 15 more minutes.
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When timer goes off remove skillet from oven and place on stovetop. Be careful, it's hot!
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Check butternut squash. If it's starting to brown, remove from oven, if not leave it in while you finish the meal.
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Remove the chicken from the skillet and set aside. Place skillet on cooktop on med/high heat. Bring chicken juices to a simmer scraping pan with a spatula or wooden spoon to separate browned bits from pan. Add kale to simmering juices. Sautee, stirring for one minute. Add barley to pan, stir mixing juices, shallots and kale. Add dried cranberries, pecans and cinnamon, stir. Sprinkle with sea salt and pepper to taste. Add butternut squash to skillet, gently folding into barley mixture.
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Either return chicken to pan and let people serve themselves or plate by placing and layer of fresh kale (optional) on plate then topping with barley. Set chicken on top!