Preheat your oven to 425°F (218°C). Halve the baby potatoes and toss them with 6 tablespoons of olive oil, ½ teaspoon black pepper, and 1½ teaspoons kosher salt. Arrange the potatoes cut-side down on a parchment-lined baking sheet. Roast for 30 minutes or until they are golden and crispy.
Heat 2 tablespoons of olive oil in a large oven-safe skillet over medium heat. Add the Italian sausage links and sear them until they develop a golden crust, about 7–10 minutes. They don’t need to be fully cooked as they’ll finish in the oven. Remove the sausage, slice into bite-sized rounds, and set aside.
Using the same skillet, cook the sliced red bell peppers for 2–3 minutes until softened. Set aside with the sausage.
Pat the chicken thighs dry with a paper towel. Season on both sides with ½ teaspoon black pepper and 1½ teaspoons kosher salt. Sear them skin-side down in the skillet until the skin is crisp, about 4 minutes per side. Remove the chicken and set aside.
Discard all the fat from the skillet except for about ¼ cup. Add the halved garlic cloves and cherry peppers, sautéing them for about 2 minutes until fragrant. Pour in the wine and red wine vinegar.
Use a wooden spoon to scrape up browned bits stuck to the skillet, creating a depth of flavor for the sauce. Reduce the liquid by half (about 5 minutes), and then add in the chicken stock. Simmer for another 5 minutes.
Return the sausage, peppers, and roasted potatoes to the skillet, tossing everything to coat it in the sauce. Arrange the chicken thighs over the top, skin side up. Cover the skillet tightly with foil and bake in the oven for 20 minutes.
Then, remove the foil and continue baking for another 15–20 minutes until the chicken reaches an internal temperature of 185–195°F (85–90°C).
Once it’s out of the oven, sprinkle the dish with freshly chopped parsley for a pop of color and freshness. Serve immediately while hot and enjoy!