Season the chicken with salt and pepper. Heat the oil in a large, deep ovenproof skillet over medium heat. Lay the chicken skinned-side down in the skillet, and brown, in batches if needed, over medium-high heat, about 4 minutes per side. Transfer the chicken to a platter.
Reduce the heat to medium, add the onion, garlic, and red pepper flakes and cook until slightly soft, about 7 minutes. Stir in the tomato paste and cook until brick red, about 1 minute. Add the wine and use a wooden spoon to scrape up any brown bits that cling to the pan. Add the beans, tomatoes, chicken broth, and Italian herbs and bring to a boil. Return the chicken along with any collected juices to the pan.
Transfer to the oven and bake, uncovered, until the chicken is cooked through, tender and lightly browned, about 25 minutes. Transfer the chicken to a platter. Return the pan to the stovetop over medium heat, stir in the escarole and cook until the greens wilt, about 4 minutes. Stir in the cheese, and season with salt and pepper, to taste. Divide the chicken among 4 plates. Spoon the sauce over the chicken and serve.
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