Trim any excess fat from the chicken thighs and pat them dry with paper towels. Lightly season both sides with 1 tsp of the kosher salt and 1/2 tsp of the black pepper.

Assemble marinade

In a large bowl combine the sliced garlic, prunes, olives, capers (with a tablespoon of their brine), oregano, and bay leaves. Add the brown sugar and stir to combine so the sugar coats the fruit and aromatics.

Add liquids

Pour the white wine, red wine vinegar and olive oil into the bowl. Whisk briefly to dissolve the brown sugar. Add the remaining 1 tsp salt and 1/2 tsp black pepper if needed and mix.

Marinate the chicken

Place the seasoned chicken in a large nonreactive dish or resealable bag. Pour the marinade mixture over the chicken, making sure pieces are coated and some prunes, olives, and garlic are on top of each piece. Cover and refrigerate for at least 4 hours and up to 24 hours, turning once or twice so flavors distribute.

Bake

Preheat oven

Remove the chicken from the refrigerator 20–30 minutes before baking to come closer to room temperature. Preheat the oven to 375°F (190°C).

Arrange in baking dish

Transfer chicken and solids to a 9x13-inch (or similarly sized) baking dish in a single layer, skin-side up. Pour the marinade liquid evenly over the pieces, distributing prunes, olives, capers, and garlic across the dish. Tuck bay leaves between pieces.

Bake covered

Cover the dish tightly with foil and bake for 30 minutes. The covered phase lets the chicken cook through and meld flavors.

Uncover and finish

Remove the foil, spoon a few tablespoons of pan juices over each piece, sprinkle any remaining brown sugar over the top if you want a slightly glazed finish, and continue baking uncovered for an additional 20–25 minutes, or until the skin is golden and an instant-read thermometer inserted into the thickest part of the chicken reads 165°F (74°C). If the skin needs extra browning, broil on high for 2–3 minutes while watching closely.

Finish & Serve

Rest the chicken for 5–10 minutes. Spoon the pan juices, prunes, olives and capers over the pieces and sprinkle with chopped parsley. Serve with lemon wedges on the side for squeezing. Transfer remaining sauce and fruit to a small bowl for guests to add more if desired.