for the beef cheeks:

Place the cleaned and trimmed beef cheeks, quartered onion, peppercorns and two bay leaves in a 6-quart dutch oven with a tight-fitting lid. Add enough water to completely cover the beef cheeks. Bring to a boil, cover and reduce heat to low. Simmer the cheeks for 2 ½ – 3 hours, until the cheeks are extremely tender.

Remove from heat. Take the meat out of the liquid and set aside, reserving the resulting beef stock in a separate container for later. Once the meat is cool enough to handle comfortably with your hands, gently pull the meat apart to shred. Set aside.

for the ropa vieja:

In the same dutch oven set over medium-high heat, add the olive oil. Once the oil is hot, add the sofrito and lightly fry until aromatic, about 2-3 minutes. Add the peppers and onion and sauté until beginning to soften, about 4 minutes. Add the cumin, oregano + sugar, and stir well to combine. Cook for 5 minutes, stirring occasionally.

Pour in the red cooking wine and deglaze the pan by scraping up any bits stuck to the bottom of the pan with a wooden spoon. This is flavor country!  Add the reserved beef stock and the crushed tomatoes. Stir well to combine.

Now, stir in the beef. Do this gently so as to not break up the tender meat. Reduce heat to medium-low and let simmer, covered, for 12-15 minutes. Add the sliced olives and the pimentos, if using, and gently stir through. Simmer for another 5-10 minutes.

for the tostones:

Whisk the water, lime juice and the ¼ cup of kosher salt until the salt is dissolved. Set aside.

Cut the ends off the plantains first, then gently cut 4 vertical slits down the entire length of the plantain peel with the tip of your paring knife, making sure not to cut into the plantain flesh. This will help you in peeling away the peel without breaking off any of the flesh. Green plantains are pretty hard and can break when pulling away the peel if you’re not careful. Cut the plantain widthwise into 1 – 1 1/2” thick rounds. The thicker you slice the plantain, the wider they will be when you flatten them.

Place the peeled rounds into the salted water and allow to sit for 10-15 minutes, no longer. This will keep the plantains from oxidizing and turning dark brown, and infuses the plantain with a touch of flavor.

In a 9” cast iron skillet heat the oil over medium heat until just shimmering. You don’t want the oil to be too hot, otherwise the outside of the plantain will crisp before the middle gets nice and tender. Working in batches, remove the plantain slices from the salted water and dry very well on paper towels.

Carefully place the plantain slices in the oil, cut-side down. Fry for about 3 minutes, then flip the slices to the other cut side. Fry for another 3 minutes, until lightly golden. Drain well on paper towels and allow to cool slightly.

If using a “tostonera” place a plantain slice, cut-side down, and flatten with the lid. Repeat with all plantain slices. Place back in the salted lime water. 

Using the same oil and skillet as before raise the heat to medium-high until very hot. Remove plantains from the lime and pat dry with paper towels. Working in batches again, carefully place in the hot oil and fry until light golden-brown in the center and crisp, about 2-3 minutes. Remove from oil and drain well on paper towels. Sprinkle some salt on each of the plantain slices as they drain on the paper towels.

To assemble, lay the fried tostones on a cutting board. Pile about 3 tablespoons of the ropa vieja onto the tostones. Feel free to use your hands to make sure you pile the beef on high and tight. Sprinkle with chopped cilantro for garnish, plate and serve with lime wedges.