Enjoy stew season while you can with an easy crockpot dinner version of this Cuban classic. Slow Cooker Ropa Vieja is loaded with tender, shredded beef in a savory simmer sauce that works on its own, over traditional rice, or even over a mash (just like other beefy stews). Use chuck roast for maximum flavor on a minimal budget.
Arrange the onions and peppers in an even layer in the bottom of the crockpot.
Divide the chuck roast into 3” chunks. Season all over with salt and pepper.
Heat oil in a 10” skillet over medium high heat. Add the chuck roast pieces in a single layer. Sear until a good crust forms, about 4 minutes. Flip the pieces and sear on at least one other side. Remove the chuck roast pieces and arrange on top of the onions and peppers.
Add the garlic to the remaining oil in the skillet. Cook, stirring constantly, until fragrant, 1-2 minutes.
Deglaze the skillet with ½ cup dry white wine or beef broth. Gently scrape up any browned bits sticking to the bottom of the pan (they’re full of flavor!). Pour the contents of the skillet over the beef, onions, and peppers.
Combine the crushed tomatoes, tomato paste, red wine vinegar, cumin, paprika, oregano, and allspice in a large bowl. Whisk until well combined. Pour the tomato mixture over the beef, onions, and peppers and gently stir into the beef.
Cover and cook on low for 8 hours.
Shred the beef right in the crockpot, or remove and shred in a shallow bowl. Return the beef to the crockpot, then add the olives, if using. Keep warm for 10-15 minutes to warm the olives through.