Season all the chicken legs with salt and fresh black pepper.
Dredge the chicken legs in the flour and shake off the excess.
Put a large cast iron skillet over a medium high flame and heat the olive oil. Place 2 of the chicken legs in the pan skin side down and cook for 6-7 minutes or until the skin is golden brown. Flip the legs over and cook and additional 5-6 minutes on the opposite side. Transfer to a plate and repeat with the remaining legs. Pour off the oil.
Preheat the oven to 450 degrees.
Add the shallots, garlic, tomatoes, olives and speck to the pan. Position the chicken legs over the ingredients and pour in the oil, wine and broth. Pull some of the thyme leaves off 2 of the sprigs and sprinkle over the chicken. Lay the rest of the sprigs in the pan.
Bring the pan to a boil on the stove and then place the pan into the oven. Roast for 40-50 minutes or until the meat pulls away from the bones.