Prep the chicken. Pat the chicken very dry, trim off any excess fat/skin, and then season all over with salt and pepper. Transfer to the fridge uncovered for 4-8 hours.
Preheat an oven to 350 F.
Cut up the sausage. Use a sharp knife to cut the italian sausage into oblong chunks. You don't need them to be perfect slices because we want them to be browned and craggy.
Sear the chicken. Heat the oil in a braiser or large oven-safe skillet over medium heat. Once the oil is hot, place the chicken in the skillet skin-side down. Reduce the heat to medium-low and brown the chicken for 7-8 minutes, until the skin is very golden brown. Flip the chicken and cook for 2 minutes, then transfer to a plate.
Brown the sausage. Add the italian sausage to the skillet and really give it a chance to brown all over. Only toss it once one side is deeply browned. After the sausage is browned all over, use a slotted spoon to transfer the sausage to a bowl. Wipe out all but 1 tablespoon of fat from the pan.
Saute the peppers, onions, and tomatoes. Add the butter to the skillet and increase the heat to medium. Add the onions, bell pepper, and cherry tomatoes to the skillet and toss to coat in the fat. Season with salt and pepper and cover the pan for 5 minutes. Remove the lid, continue to cook until the tomatoes have burst and reduced slightly. Use a wooden spoon to scrape up any browned bits from the bottom of the pan.
Build the sauce. Add the sliced garlic, tomato paste, and minced oregano leaves to the skillet and cook for 1 minute, until fragrant. Deglaze the pan with the white wine and cherry pepper juice and bring to a simmer. Reduce by one third, then stir in the chicken stock and sliced cherry peppers and season with salt and pepper. Bring to a gentle simmer.
Braise. Nestle the chicken, skin-side up, into the sauce along with the sausage. Cover and transfer to the oven. After 30 minutes, remove the lid and continue cooking for another 35 minutes. Check the internal temperature to ensure that it’s reached at least 185-190 °F. Remove from the oven and squeeze the lemon over the top of the chicken. Top with minced parsley and more minced oregano and serve right away.