Heat a very large skillet over medium heat. Add beef and sausage; cook and stir until browned, 8 to 10 minutes. Drain excess grease and transfer to a large pot.
Heat olive oil in the skillet over medium-high heat. Add bell peppers, Anaheim chile peppers, onion, jalapeno peppers, and garlic; cook and stir until golden brown, about 5 minutes. Stir into beef mixture.
Stir chili beans, diced tomatoes, kidney beans, tomato paste, chili powder, cumin, salt, cayenne, black pepper, and cinnamon into the beef and peppers mixture. Bring to a boil over medium-high heat, stirring frequently. Reduce heat to low and cover; simmer, stirring occasionally, until flavors combine, about 3 hours.
