Cuban Ropa Vieja Sandwich with Plantain Chips

Season the flank steak generously with 1/2 teaspoon salt and 1/4 teaspoon black pepper. In a large Dutch oven or heavy-bottomed pot, heat 1 tablespoon olive oil over medium-high heat. Sear the steak for 3-4 minutes per side until browned, then remove and set aside.

Add the sliced onion and green bell pepper to the pot, reducing heat to medium. Sauté for 5-7 minutes until softened. Add the minced garlic, ground cumin, and dried oregano, cooking for 1 minute until fragrant.

Return the seared steak to the pot. Pour in the crushed tomatoes, beef broth, and dry white wine. Add the remaining 1/2 teaspoon salt and 1/4 teaspoon black pepper. Bring to a simmer, then reduce heat to low, cover, and cook for 2.5-3 hours, or until the steak is very tender and easily shredded with a fork.

Remove the steak from the pot and shred it using two forks. Return the shredded beef to the sauce, stir in the apple cider vinegar, and simmer uncovered for 15-20 minutes, allowing the sauce to thicken slightly.

While the ropa vieja simmers, prepare the plantain chips. Peel the green plantains and slice them very thinly, about 1/8 inch thick, using a mandoline or sharp knife. Heat 2 cups vegetable oil in a deep skillet or pot over medium-high heat to 350°F/175°C.

Carefully fry the plantain slices in batches for 2-3 minutes per side, until golden brown and crispy. Remove with a slotted spoon and place on a paper towel-lined plate to drain. Season immediately with a pinch of salt.

Slice the Cuban bread or rolls lengthwise, without cutting all the way through. Lightly toast the bread if desired. Fill each piece of bread generously with the shredded ropa vieja.

Serve the Cuban Ropa Vieja Sandwiches immediately with the freshly made plantain chips on the side.