Heat olive oil in a large skillet on high heat about 2 minutes. Add chicken, skin side down, cover, and cook until golden brown, about 10 minutes. Flip chicken, cover again, and cook until golden brown on the second side, about 5 minutes. Add garlic and cook stirring one minute.
Arrange prunes, olives and capers, brine, bay leaves, and oregano in between chicken pieces. Sprinkle with brown sugar, 1 tablespoon salt, 1/2 teaspoon pepper. Pour vinegar and wine over top and bring to a boil. Reduce to low and cover and simmer until is cooked through 15 to 20 minutes.
Transfer chicken to a serving platter and return pan to high heat. Cook sauce, swirling occasionally until reduced and slightly thickened about 5 minutes. Spoon pan sauce over chicken and serve.