- In a small bowl, combine the dried ancho chiles, dried chipotle chiles, and enough boiling water to cover. Let stand for about 10 to 15 minutes or until softened. 
- Remove and discard the stems and seeds. Transfer the chiles to a blender and about 1/4 cups of the soaking liquid. Pulse a few times to a smooth paste. 
- Trim chuck roast of excess fat and cut into about 1/4 inch cubes. You should have about 2 pounds after trimming. 
- In a Dutch oven over medium-high heat, heat oil. Add beef and cook for about 2 to 3 minutes on each side or until lightly browned. Remove from pot and keep warm. 
- Lower heat to medium and add the remaining oil to pan as needed. 
-  Add onions and garlic and cook for about 2 to 3 minutes or until softened.  
- Add beef broth and bring to a boil, scraping any browned bits on the bottom of the pot. 
- Return the beef to the pot including any juices.  
- Add crushed tomatoes, pureed chiles, cumin, brown, sugar, and salt. Stir to combine. 
- Lower heat, cover, and simmer for about 2 hours or until meat is tender but not falling apart. If the chili is drying before the meat is tender, add more beef broth or water as needed. 
- Add pinto beans and kidney. Continue to simmer until sauce is thickened and reduced to about 2 cups. 
- Transfer to serving bowls and top with shredded cheddar and onions as desired. Serve hot.