Preheat the oven to 400℉. Add oil to an oven safe skillet on medium heat. Pat chicken dry and season with salt and pepper on both sides.Add chicken to the skillet skin side down and cook until golden brown, about 5 minutes per side. Transfer chicken to a plate. Add sausage to the skillet and cook for about 6 minutes,turning occasionally, until golden. Transfer to the same plate as the chicken.

Thinly slice both the onion and bell pepper and add both to the skillet and cook, stirring occasionally for about 5 minutes. Onion and bell pepper should be soft. Add garlic and cook for 1 more minute. Add wine and bring to a simmer. Cook down for about 7 minutes until reduced to about half. Add cherry peppers, pickling juice, vinegar, and broth. Bring to a simmer again and add Italian seasoning and salt and pepper to taste.

Cut each sausage into roughly 5 pieces and add to the skillet. Nestle the chicken in between the sausage and peppers. Put the skillet in the oven and cook until the chicken is cooked through, about 25 minutes. Check on it occasionally, a thermometer should read 165℉. Serve with potatoes, pasta, rice or bread. Enjoy!