Heat olive oil in a large Dutch oven or oven-proof pot over medium-high heat. Add the chuck roast and cook until browned on all sides. Remove from the pan and set aside.
Add the onion, garlic, and bell pepper to the pot and cook until the vegetables are softened, about 5 minutes. Add the oregano and cumin and cook for another minute.
Add the diced tomatoes, white wine, and cilantro to the pot. Season with salt and pepper, to taste. Stir to combine.
Return the chuck roast to the pot and spoon the tomato mixture over the top. Cover the pot and transfer to the preheated oven.
Bake the chuck roast in the preheated oven for 1 1/2 hours, or until the beef is very tender and shreds easily with a fork.
Remove the pot from the oven and shred the beef with two forks. Serve the shredded beef with the tomato sauce over rice, beans, or vegetables.
Interesting Facts
Ropa Vieja means "old clothes" in Spanish.
The dish is said to have originated in the Canary Islands.
Ropa Vieja is a popular dish in Cuba, Puerto Rico, and other Caribbean countries.