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Step 1
Place the dried chiles in a pot and add the 2 cups of water. Bring to a simmer. Cook for 10 minutes, or until the chiles are very tender.
Step 2
Transfer the mixture to a blender and blend until smooth, being careful to occasionally vent the top of your blender to avoid an explosion from the heat.
Step 3
Meanwhile, set your slow-cooker to the SEAR setting (if you don’t have this option, heat a large cast-iron skillet over medium-high heat).
Step 4
Add the oil to the slow-cooker/skillet. Place the cubed chuck roast on a cutting board or plate and season on all sides with salt and pepper. Sprinkle the flour over the meat cubes and toss to lightly and evenly coat the beef with the flour.
Step 5
Add the flour-coated meat, in batches, to the hot pot/pan. Sear on all sides to form a crust. If using a skillet, transfer the seared meat to your slow cooker.
Step 6
Once all the meat has been seared, pour in the blended chile liquid, along with the onion, garlic, spices, beef broth, canned tomatoes, sugar, espresso powder, chipotle pepper, adobo sauce, and the bittersweet chocolate.
Step 7
Stir to combine and then add in the salt and pepper.
Step 8
Cover the slow-cooker and cook on LOW for 8-10 hours or on HIGH for 4-6 hours, stirring occasionally if possible.
Step 9
Add the beans to the pot and cook for another 30 minutes on HIGH. The chili is ready when it is thickened and the meat is falling apart. Season, to taste, with salt, pepper, or more adobo sauce (for more heat).
Step 10
Ladle the chili into bowls and garnish as desired with sour cream/yogurt, lime wedges, chopped scallions, chopped cilantro, and slices of avocado.
Step 11
This can easily be made on a stovetop instead of in a slow cooker or crock pot.
Step 12
Sear the beef in batches in a large pot, remove, and then saute the onion and spices in the same pot until tender.
Step 13
Add the other ingredients along with the beef and simmer on the stove, partially covered, for a couple hours. Add the beans, as directed in the recipe above.