OPTIONAL: Pat dry the chicken thighs and place on a sheet pan, uncovered, and refrigerate to allow the skin to dry out for 4 to 8 hours. This isn’t necessary, but it does lend to a crispier skin.
Preheat the oven to 375℉. Pat dry the chicken and season all over with salt and pepper.
Heat the oil in a large, oven safe skillet (preferably a 3.5 quart-braiser) over medium heat.
Add the pancetta, cook, stirring, until the pancetta is cooked through and crisp, about 5 minutes. Using a slotted spoon, transfer to a paper towel lined plate and set aside. Discard all but 2 tablespoons of the fat in the pan.
Increase the heat to medium-high and arrange the chicken, skin side down, in a single layer and cook until a golden-brown crust forms, 6 to 8 minutes. Transfer the browned chicken to a plate and set aside.
Reduce the heat back down to medium and add the carrot and shallot and continue to cook, stirring, until they begin to soften, about 3 minutes. Add the garlic and mushroom and continue to cook, stirring, being careful not to burn the garlic, until the mushrooms begin to soften, another 3 minutes.
Stir in the tomato paste until it is well combined. Sprinkle in the flour and cook, stirring, until it is well-combined and begins to toast, 1 to 2 minutes.
While stirring, slowly pour in 1 cup of red wine until it is well incorporated, scraping up any browned bits on the bottom of the pot. Slowly stir in the remaining 1 cup of red wine and the ½ cup of chicken broth. Add a small pinch of salt and a few cracks of black pepper. Bring to a gentle simmer.
Add the cooked pancetta back to the sauce. Using kitchen twine, tie the thyme and rosemary sprigs into a herb bouquet and toss into the sauce along with the bay leaf. Nestle the chicken, skin side up, into the sauce.
Transfer to the oven and bake until the chicken is cooked through and very tender, and the top is golden brown, about 45 minutes.
Remove from the oven and let rest for 5 minutes to allow the juices to settle. Garnish with fresh parsley. Serve over mashed potatoes and/or with crusty bread. Enjoy!