In a small bowl, whisk together ¼ cup of the olive oil, vinegar, capers, oregano, honey and ¼ teaspoon salt. Set aside.
Heat 1 tablespoon olive oil in a Dutch oven or braising pan over medium-high heat. Sprinkle the chicken with salt and pepper. Cook chicken meaty side down for about 6-7 minutes or until well browned. Don't crowd the pan, work in batches if you need to. Remove the chicken and set aside.
Add the garlic to the pan and cook, stirring, for about 2 minutes until browned.
Add the wine and bay leaves and cook until reduced by half, about 4 minutes.
Stir in the olives and the prunes and nestle the chicken back into the pan. Pour the vinegar mixture over the top and tuck in the orange slices.
Cover and bake for 40 minutes (45 if using whole chicken legs.) Uncover and bake for 10-15 minutes. Remove the bay leaf, sprinkle with fresh ground black pepper to serve.
Notes
If you don't have fresh oregano, you can substitute 1 teaspoon of dried oregano.