Marinate the Beef: In a large bowl, combine beef with Cuban seasoning, salt, pepper, garlic, olive oil, orange juice, lime juice, and vinegar. Toss thoroughly and marinate 30 minutes to 4 hours. Sear the Beef: Pat beef lightly dry, reserving marinade. Heat a Dutch oven over medium-high heat. Sear beef in batches until deeply browned on multiple sides. Remove and set aside. Build the Flavor Base: Reduce heat to medium. Add olive oil if needed. Add onion and bell pepper. Cook 5 to 6 minutes until softened. Stir in tomato paste and cook 2 minutes until darkened. Add Cuban seasoning and bay leaves. Deglaze: Pour in white wine. Scrape up browned bits from the bottom of the pot. Let reduce by half.
Braise: Return beef to pot. Add reserved marinade, crushed tomatoes, beef broth, Worcestershire sauce, and sugar. Bring to a gentle simmer. Cover and cook 60 to 75 minutes until beef is fork-tender.
Add Vegetables: Add potatoes and carrots. Simmer uncovered 20 to 25 minutes until vegetables are tender and sauce is thick and glossy.
Finish: Stir in olives and capers during the final 5 minutes. Adjust salt or acidity if needed. Rest 10 minutes before serving. Garnish with cilantro.
