Adjust oven racks to accommodate dutch oven/pot. Preheat oven to 350°F.
Heat a large skillet (12-inch) over high heat. Once skillet is hot, add torn ancho chili. Press chili into pan, toasting it. Toast chili for 20 seconds on each side. Toast until fragrant*. Remove from pan and allow to cool in food processor bowl.
In a food processor, combine dried ancho chili, cornmeal, oregano, and cumin until it resembles coarse sand. Add 2 chipotle peppers, 1 Tbsp adobo sauce, and ½ cup chicken broth. Pulse to create a thick paste. Transfer paste to a clean bowl. Do not clean out food processor bowl.
Add garlic to food processor. Pulse until minced. Add onions and jalapeños. Pulse until mixture resembles chunky salsa.
In dutch oven/large pot, heat up 1 Tbsp oil over medium heat. Add onion mixture. Cook for 2 minutes until onions have softened. Add chili paste. Stir to combine. Add diced tomatoes (including juice), brown sugar, salt, pepper, and 2 cups of chicken broth. Bring to a boil. Lower heat and allow mixture to simmer while you cook beef.
In the same skillet used to toast chili, add remaining 1 Tbsp of vegetable oil. Heat skillet over medium-high heat.
Sear beef chunks in batches. Turn beef chunks as needed to ensure all sides are seared. You don't need to fully cook the beef, just brown the sides. The beef will continue to cook and soften in the chili. Place seared beef in simmering chili pot. Continue to sear remaining beef chunks. Once all the beef has been placed in the chili pot, deglaze the skillet using the remaining ½ cup of chicken broth. Pour deglazing sauce into chili pot and stir.
Add rinsed and drained black beans to pot. Stir to combine. Cover dutch oven pot with lid. Place in oven and allow to bake for 2 hours, until beef is tender. Cool chili for 10 minutes before removing lid.
Season chipotle steak chili with salt and pepper as needed.**
Serve chili warm with garnishes and cornbread.