Heat 1 tbsp olive oil in a large skillet over medium heat. Add the ground beef and cook for 5 to 7 minutes, breaking it up as it browns. Remove the beef with a slotted spoon, discard grease, and set beef aside. Add the remaining 1 tbsp olive oil to the same skillet. Add the onion and bell peppers and cook for 3 to 5 minutes until softened.
Stir in the grated garlic and tomato paste and cook for about 30 seconds. Add the Cuban seasoning and cook for 30 to 60 seconds until fragrant.
Pour in 1 1/4 cups chicken broth and scrape up any browned bits from the pan.
Return the beef to the skillet. Add the olives, raisins, capers, and bay leaves. Bring to a gentle simmer.
Cook uncovered for 35 to 40 minutes, stirring occasionally, until the sauce reduces and becomes thick and glossy. Add additional broth as needed.
Season with salt to taste after simmering. Discard bay leaves before serving.
Garnish with chopped cilantro and serve warm with white rice and fried plantains.
