2 Tbl. olive oil
Salt and pepper to taste
2 lbs. flank steak or top round
1 medium Spanish onion, chopped
1 green pepper, chopped
1 small red pepper, chopped
4 garlic cloves, minced
1 Tbl. tomato paste
1/3 cup apple cider vinegar
1 14.5 oz. can diced tomatoes with juice
1 large bay leaf
1Tbl. ground cumin
1 Tbl. dried oregano
1/4 tsp. red pepper flakes
1 5 oz. jar sliced green olives with brine or 1 cup sliced green olives with 3 Tbl. brine (with or without pimentos is fine)
1/2 cup brown sugar
2 cups water, divided
Fresh cilantro for garnish
Heat olive oil in large skillet over medium-high heat. Season both sides of flank steak with salt and pepper. Cook flank steak on both sides until brown, about 5 minutes per side. Pour 1 cup of water in bottom of clay pot. When flank steak is browned, place in bottom of clay pot.
Reduce heat to medium, add onions and peppers to skillet and saute for about 10 minutes or until onions start to brown. Add garlic and stir for 1 minute.
Add tomato paste, cook and stir for 2 minutes. Carefully add vinegar to pan and scrape up any brown bits from bottom of pan. Add diced tomatoes, olives and brine, cumin, oregano, bay leaf, brown sugar and remaining 1 cup of water. Stir to combine and pour over flank steak in clay pot.
Cover clay pot with lid and place in cold oven. Set oven temperature to 375° F and cook for 2 1/2 - 3 hours or until flank steak is tender and falling apart. Remove baker from oven and shred flank steak lengthwise (it should be falling apart on its own). Return shredded beef to clay pot, stir to coat beef with the sauce, cover with lid, place back in oven for 25 minutes. Discard bay leaf and adjust seasonings if necessary. Serve over rice with black beans and garnish with chopped fresh cilantro.