Preheat the oven to 350F. Drizzle 1 tablespoon olive oil in the bottom of a large roasting pan. Add the tomato, onion, zucchini, yellow summer squash, eggplant, red bell pepper, garlic, rosemary, thyme, 1 ¼ teaspoons salt, and ½ teaspoon black pepper to the roasting pan and toss to combine. Cover the pan with foil and roast for 45 minutes.
Remove the foil from the top of the roasting pan, and stir in the crushed tomato. Securely fit a wire rack over the top of the roasting pan and arrange the chicken on top, skin side up. Rub the remaining 1 tablespoon oil on top of each piece of chicken, and then sprinkle on the remaining ¼ teaspoon salt and ⅛ teaspoon black pepper. Roast until the chicken is fully cooked (there should be no pink when you cut into it), about 1 hour.
Serve hot.
Notes
Storage: Store leftovers covered in the fridge for up to 4 days.
If you prefer the final dish less stew-like and more dry: Omit the crushed tomatoes and add ½ cup chicken broth instead.