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Preheat the oven to 350ºF.
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If your flank steak is too big to fit comfortably in your pot or large Dutch oven, cut it into smaller pieces. Pat the beef dry with paper towels and season the meat with salt and ground black pepper.
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In a large pot or Dutch oven, heat about 2 tablespoons of oil over medium high heat. Once hot, add the beef and sear on both sides until golden brown, about 3-4 minutes per side. Do this in batches if needed not to overcrowd the pot. Transfer the meat to a plate and set aside.
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In the same pot, heat the remaining oil. Add the onions and bell peppers and cook, scraping down the bottom of the pot to remove any browned bits, Cook the vegetables, stirring frequently until they become tender, about 5-7 minutes. Lower the heat to medium-low and stir in the garlic. Cook for an additional minute or until the garlic becomes aromatic.
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Stir in the tomato paste, dried oregano, cumin, all spice and paprika. Cook for about a minute then, add the white wine and bring to rapid boil, deglazing the pan by scraping up any browned bits from the bottom of the pot. Cook for 1-2 minutes to cook off the alcohol in the wine then stir in the broth and crushed tomatoes and return the beef to the pot and any accumulated juices.
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Add the carrots, celery and bay leaves tucking all the ingredients under the sauce. Add additional broth if needed to keep all ingredients under the sauce. Bring to a boil then cover the pot and transfer it to the preheated oven. Cook until the beef is tender and shreds easily, about 1 1/2 hours.
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Remove the carrots, celery and bay leaves. Transfer the meat to a plate and with two forks shred the meat into thin, long shreds. Return the beef to the pot and stir in the olives, pimento and capers. Simmer, uncovered over medium heat until the sauce reduces and thickens
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Season to taste and stir in the cilantro. Serve with rice or rice and black beans and fried ripe plantains.