In a medium bowl, combine the ancho chili powder, brown sugar, onion powder, garlic powder, Italian seasoning, cumin, and allspice. Mix well until evenly blended, creating the flavorful chili seasoning.

Take your 3 lb chuck roast and cut it into 1 1/2-inch pieces for optimal tenderness. Sprinkle the chunks with salt, pepper, and 1 tablespoon of the seasoning mixture. Make sure all sides are well-coated.

In a large skillet, heat 2 tablespoons of vegetable oil over medium-high heat. Add the seasoned roast pieces in batches, searing each side for about 3–4 minutes until browned and caramelized.

Remove the meat and in the same skillet, add the diced onion, bell pepper, and jalapeños. Sauté over medium heat for about 5–7 minutes, or until softened and slightly caramelized.

Transfer the seared meat and sautéed vegetables into your crockpot. Add the crushed tomatoes, diced tomatoes, tomato paste, drained chili beans, Worcestershire sauce, beef broth, and the remaining seasoning mixture. Stir everything together until well combined.

Cover the crockpot with its lid and set it to cook on HIGH for 6–7 hours or on LOW for 10–12 hours.

Once your chili is done cooking, carefully taste the mixture and adjust the seasoning if needed, adding salt and pepper as needed.

Spoon the comforting chili into bowls and serve hot. Garnish with toppings of your choice, such as sharp cheddar cheese, sour cream, green onions, or avocado slices.