Cuban Ropa Vieja

2 pounds flank steak
Salt and ground black pepper to taste
3 tablespoons olive oil, avocado or vegetable oil, (divided) or more if needed
1 large onion, thinly sliced
3 bell peppers, red, green and yellow thinly sliced
6 cloves garlic, minced
1 tablespoon tomato paste
1 teaspoons dried oregano
1 teaspoon ground cumin
1 teaspoon sweet paprika
1/2 teaspoon ground allspice
1/8 teaspoon ground cloves
1/2 cup white wine
1 cup chicken broth or more if needed
1 14-ounces can crushed tomatoes
1 carrot, peeled and cut into thirds
1 celery rib, cut into thirds
2 bay leaves
1 cup pimento-stuffed Manzanilla olives, drained and sliced
1 4-ounces jar sliced pimentos
2 tablespoons capers, drained (optional but recommended)
1 teaspoon chicken bouillon optional
Chopped cilantro or parsley

Stove Top/Oven

  1. Preheat the oven to 350ºF.
  2. 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.
  3. 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.
  4. 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.
  5. Stir in the tomato paste, dried oregano, ground cumin, sweet paprika, all-spice and ground cloves, (Add bouillon if using). 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.
  6. 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.
  7. 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 (add the bouillon if using). Simmer, uncovered over medium heat until the sauce reduces and thickens.
  8. Season to taste and stir in the cilantro. Serve with rice or rice and black beans and fried ripe plantains.
    Crock Pot / Slow Cooker
  9. Follow the stove top instructions from step 2 to 5 then, place the carrots and celery at the bottom of the slow cooker. Place half of the pepper and onions on top. Place the seared flank steak on top of the vegetables and pour the rest of the onion/pepper mixture on top.Stir in the wine, broth, tomato paste, crushed tomatoes, dried oregano, ground cumin, sweet paprika, all-spice and ground cloves and bay leaves. Gently mix to combine.
  10. Cook covered on low for 8 hours hours or on high for about 4.5 to 5 hours until the beef is tender and shreds easily with 2 forks. Return the meat to the crockpot and stir in the olives, pimento and capers (add bouillon if using). Cook on high for 15-20 minutes or until the sauce reduces and thickens a bit. Finish the recipe as instructed above.
    Instant Pot / Pressure Cooker
  11. Follow the stove top instructions from step 2 to 5 using your Instant pot sauté function to sear the beef and sauté the vegetables. Add the carrots, celery and bay leaves tucking all the ingredients under the sauce.
  12. Close the lid and seal the pot. Cook on high pressure for 45 minutes then allow the pressure to release naturally for 15 minutes. Release the remaining pressure.
  13. Open the lid, transfer the meat to a plate and shred the beef. Return the beef to the pot and stir in the olives, pimento and capers (add bouillon if needed). Turn on the Instant Pot sauté function. Cook uncovered for 5-8 minutes or until the sauce reduces and starts to thicken. Make sure the beef is submerged in the sauce so stays moist.