Place it on a plate or sheet tray and generously season all sides with salt and pepper.
Pour the 2 tablespoons of oil into a large rondeau or sauce pot and heat over high heat until it begins to smoke lightly.
Add in the seasoned beef and sear for 3 to 4 minutes per side or until well browned.
Set the steak to the side on a plate and in the same pan add in 1 large diced yellow onion and sauté over medium heat for 6 to 8 minutes or until well browned. Be sure to scrape the fond off the pan while cooking these to release more flavor.
Stir in the garlic smashed cloves and cook for 30 to 45 seconds or just until fragrant.
Deglaze with beef stock and add in the 2 bay leaves, peppercorns, salt, and seared beef and cook covered over low to medium heat for about 90 to 120 minutes or until very tender and shreds apart with ease.
Once the beef is done cooking, remove them from the pan and use two forks to shred into long thing shreds. Strain the braising liquid and set it to the side.
With about 30 to 40 minutes left in the cooking process add the remaining 2 tablespoons of olive to a rondeau or sauce pot and low to medium heat and caramelize the 1 julienne yellow onion while occasionally stirring, which takes about 20 to 25 minutes.
Next, stir in the garlic and cook just until fragrant which takes about 30 to 45 seconds.
Turn the heat up to medium high and add in the peppers and sauté for 4 to 6 minutes or until they start to get a little brown on them.
Stir in the cumin and oregano, and then deglaze with the white wine and cook it until it is completely absorbed, which takes 1 to 2 minutes.
Stir the shredded beef along with the pureed tomatoes, 1 ½ cups remaining braising liquid, and season with salt and pepper to the pan of peppers and onions and cook covered over low to medium heat for 15 to 20 minutes to infuse the flavors.
Finish with chopped cilantro and sliced green olives.
Serve by itself or with the classic white rice, Cuban Black Beans, and Maduros.
Notes
Make-Ahead: This is meant to be eaten once it is finished cooking. However, you can keep it warm over very low simmering heat for up to 1 hour before serving.How to Store: Cover and store the ropa vieja in the sauce in the refrigerator for 3-4 days. You can cover it and freeze it for up to 3 months. Thaw in the refrigerator for 1 day before reheating.How to Reheat: Add the desired amount of meat to a rondeau or saucepot along with some of the sauce and cover and heat over low heat for 10 to 12 minutes or until warm. You may want to add ¼ to ½ cup of water or beef stock to help loosen up the mixture as it reheats.Doing the additional sear to the beef and braising it in the beef stock will render a more flavorful ropa vieja.Feel free to add 1 roughly chopped rib of celery and 2 peeled and roughly chopped carrots to the beef as it braises for more flavor.Strain the braising liquid from the vegetables and use it as a sauce or in another recipe, as it is extremely flavorful.