1. Heat the olive oil in a enameled cast-iron casserole. Add half the ground beef in large chunks and season with salt and pepper. Cook over moderately high heat until brown on the bottom, about 4 minutes. Stir and cook until most of the pink is gone, about 3 minutes; keep the meat in large chunks. Transfer to a plate and repeat with the remaining meat.
2. Pour off all but 2 tablespoons of the fat from the casserole. Add the onion, garlic and jalapeños and cook over moderately low heat, stirring often, until softened, about 6 minutes. Add the ancho powder and paprika and cook over low heat, stirring often, until fragrant, about 5 minutes. Add the tomato paste and cook, stirring, until the paste is glossy and starts to brown, about 5 minutes. Stir in the tomatoes and their juices, the chicken stock and the cooked beef and any accumulated juices. Bring to a simmer over moderately high heat. Reduce the heat to low and simmer for 1 1/2 hours, stirring occasionally.
3. Add the kidney beans, chipotles and oregano and simmer for 30 minutes longer. Season with salt, pepper and a large pinch of cinnamon. Remove from the heat and let stand for at least 20 minutes. Reheat before serving.
4. Serve the chili in bowls, topped with a generous sprinkling of cilantro. Pass the sour cream at the table.
Make Ahead: The chili can be refrigerated for up to 4 days and frozen for up to 2 months.