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.