In a large skillet, heat the oil over medium-high heat. Add the beef chuck roast, searing it for about 4–5 minutes until browned. Transfer the meat to your crock pot.

In the same skillet, add the diced onion, bell pepper, jalapeños, and minced garlic. Sauté for 3–4 minutes until the vegetables soften. Add these to the crock pot with the beef.

In the crock pot, add the browned beef and sautéed vegetables. Stir in the crushed tomatoes, diced tomatoes, and tomato paste. Sprinkle in the ancho chili powder, ground cumin, onion powder, garlic powder, Italian seasoning, and allspice.

Drain and rinse the beans and add them to the crock pot. Pour in the beef broth and Worcestershire sauce. Season with salt and black pepper to taste.

Cover the crock pot and set it to low for 8 hours or high for 4 hours.

Once cooked, ladle the chili into bowls. Garnish with toppings like shredded cheese, sour cream, or fresh cilantro.