Combine the olive oil, red wine vinegar, prunes, olives, capers, bay leaves, minced garlic and oregano with 2 tablespoons salt and 2 teaspoons pepper in a large bowl. This is your marinade.
Add your chicken to the marinade. Refrigerate overnight, turning occasionally to be sure the marinade is getting into all of the chicken pieces. Alternatively, you can use a large zip-top bag.
Preheat your oven to 350°F. Place the chicken, skin side up, along with the marinade in one layer in a large roasting pan. Sprinkle with ½ cup brown sugar, 2 teaspoons salt, and 1 teaspoon pepper. Pour the wine or stock around (not over!) the chicken.
If using bone-in chicken, roast for 30-35 minutes, until the internal temperature of the chicken is 145°F. If using boneless, roast for 20-25 minutes.
Remove the pan from the oven, cover tightly with aluminum foil, and allow to rest for 10-15 minutes. Discard the bay leaves.
Transfer the chicken to a serving platter, sprinkle with salt, and serve hot with the pan juices.
Recipe Note
Note: The "cook time" of this recipe does not include the overnight marinade - make sure to plan ahead, or combine ingredients before you leave for work, to make that same night!