Preheat oven to 325 degrees. Rinse the chicken under cold running water and pat dry. Crush two of the 20 garlic cloves.
Place an ovenproof skillet over moderate heat. Once warm add oil. Once oil is hot, add crushed garlic to pan then place chicken in the pan on top of the garlic. Toss in remaining garlic cloves.
Cook chicken for about 8 minutes or until it will release itself easily from the pan then flip to cook the other side. Continue to cook for 4 minutes.
Remove the chicken from the skillet. Set aside.
Place onions and tomatoes over the caramelized garlic. Allow the onions and tomatoes to sweat in the pan for 3-4 minutes. Reduce heat and add wine. With a spoon stir the pan to remove the browned bits from the bottom of the pan. This deglazing technique will remove the flavor stuck to the bottom of the pan and release it to the vegetables.
Add chicken back to the skillet. Add stock just until the liquid level reaches halfway up the sides of the chicken. Add oregano and pepper to taste. Cover with tight fitting lid and place in oven. Bake 30 minutes.
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