Authentic Cuban Ropa Vieja with Flank Steak

Ingredients

• 1 1/2 pounds chuck roast or flank steak
• 1 tablespoon olive oil
• 1 large yellow onion (thinly sliced)
• 1 medium red onion (thinly sliced)
• 1 teaspoon sugar
• 2 large red bell peppers (thinly sliced)
• 4 cloves garlic minced
• 2 teaspoons dried oregano
• 1 teaspoon dried thyme
• 1 teaspoon dried basil
• 2 teaspoons ground cumin
• 1 tablespoon sweet smoked paprika
• 1/2 teaspoon ground allspice
• 1/2 teaspoon ground cloves
• 2 teaspoons kosher salt
• 1 teaspoon freshly ground black pepper
• 1 cup dry white wine
• 1 cup beef broth
• 16 ounce can crushed tomatoes
• 6 ounce can tomato paste
• 2 bay leaves
• 1 cup Green Olives with pimentos and brine
• 1/3 cup chopped fresh parsley

Instructions

1. 1

   Pat the beef dry and season with salt and freshly ground black pepper. Heat a olive oil in a Dutch oven over high heat. Once very hot add the beef and brown generously on all sides. Transfer the beef to a plate. Leave the drippings and any remaining browned bits in the pot. If necessary add some more oil to the pot.

2. 2

   Add the sliced onions to the pot and cook over medium heat for 15-20 minutes until caramelized. About halfway through add the sugar to help with caramelization.

3. 3

   Add the bell peppers and saute for another 2-3 minutes.

4. 4

   Add the garlic and spices and cook for another minute.

5. 5

   Add the tomato paste and stir in. Add crushed tomatoes and bay leaves. Simmer for 5 minutes.

6. 6

   Add the white wine and bring it to a rapid boil, deglazing the bottom of the pan with a wooden spoon.

7. 7

   Add the broth and mix well.

8. 8

   Simmer uncovered to thicken the sauce for 30 minutes. If you have time stop at this step, refrigerate and let sit overnight as the flavors will come together even more.

9. 9

   Return the roast to the pot. Bring to a boil, reduce the heat to low, cover and simmer for 3-4 hours or until the beef is fork tender and falls apart easily. Discard the bay leaves.

10. 10

    Remove the beef and transfer to a plate and shred it. Stir in the olives and its liquid and bell peppers.

11. 11

    Stir in the parsley and add salt and pepper to taste.

12. 12

    Optional serve with rustic bread to make a sandwich.