Pat the flank steak completely dry with paper towels. Season generously on both sides with kosher salt and black pepper. Heat 2 tbsp olive oil in a large Dutch oven over medium-high heat until shimmering. Sear the steak for 3-4 minutes per side until a deep brown crust forms. Transfer to a cutting board.
Reduce heat to medium. Add remaining 1 tbsp olive oil to the Dutch oven. Add sliced onions and bell peppers; cook for 8-10 minutes, stirring occasionally, until softened and lightly caramelized. Add minced garlic and cook for 1 minute until fragrant.
Stir in tomato paste and cook for 2 minutes, stirring constantly. Add cumin, oregano, paprika, and cayenne; toast the spices for 1 minute until fragrant. Deglaze with red wine vinegar, scraping the bottom of the pot.
Add crushed tomatoes, beef broth, and bay leaf. Stir to combine. Return the seared steak to the pot, nestling it into the liquid. Bring to a gentle simmer, then reduce heat to low. Cover and braise for 60-75 minutes until the meat is fork-tender and shreds easily.
Remove the steak from the pot and transfer to a cutting board. Using two forks, shred the meat against the grain into bite-sized pieces, discarding any remaining fat. Discard the bay leaf from the braising liquid.
Return the shredded beef to the Dutch oven, stirring gently to combine with the sauce. Simmer uncovered for 5 minutes to allow flavors to meld. Taste and adjust seasoning with additional salt, pepper, or vinegar as needed for balance between acidity and richness.
Inspired by Cory Morris’s winning ropa vieja. This is a plausible recreation, not the chef’s original recipe.