Preheat oven to 350° F. In a large, oven-safe skillet, heat olive oil over medium heat. Season the oxtail with the salt and pepper and add the pieces to the skillet. Cook over medium- high heat, turning occasionally so they brown evenly. Drain the fat from the skillet, add the vinegar, celery, carrots, chipotle peppers, onions and garlic. Cook, stirring for 10 minutes.
Stir in the wine. Cover and transfer to the oven. After 15 minutes, add the tomato paste. Cook, stirring occasionally, for 3 hours; the meat should be fork tender. Remove from oven and pick meat off the bone. Add 2 cups of water to skillet with oxtail meat. Return to oven and cook for another 45 minutes. Serve over grilled bread.
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