Place 6 large dried ancho chiles (about 3 oz.), stemmed, seeded, coarsely torn, in a medium bowl. Pour enough boiling water over to cover. Soak until chiles soften, at least 30 minutes and up to 4 hours.

Preheat oven to 350°. Cook 6 oz. bacon, finely chopped, in a heavy large Dutch oven or other ovenproof pot over medium-high heat, stirring frequently, until beginning to brown. Add 1¼ lb. onions, chopped (about 4 cups), then reduce heat to medium. Cover and cook until tender, about 5 minutes. Sprinkle one 5-lb. flat-cut beef brisket, cut into 2½"–3" cubes, all over with kosher salt and freshly ground black pepper. Add to pot; stir to coat. Set aside.

Drain chiles, reserving soaking liquid. Place chiles in a blender. Add 1 cup soaking liquid, 6 large garlic cloves, peeled, 2 Tbsp. chili powder, 2 tsp. cumin seeds, 1 tsp. dried oregano, 1 tsp. ground coriander, and 1½ tsp. Diamond Crystal or ¾ tsp. Morton kosher salt; blend to purée, adding more soaking liquid by ¼ cupfuls if very thick. Pour purée over brisket in pot. Add 1¾ cups fire-roasted diced tomatoes with green chiles with juices, one 12-oz. bottle Mexican beer, one 7-oz. can diced roasted green chiles, and ½ cup finely chopped fresh cilantro stems. Stir to coat.

Bring chili to simmer. Cover and place in oven. Cook 2 hours. Uncover and cook until beef is almost tender, about 1 hour. Add 4 cups 1½"–2" chunks seeded peeled butternut squash (from a 3½-lb. squash); stir to coat. Roast, uncovered, until beef and squash are tender, adding more soaking liquid if needed to keep meat covered, about 45 minutes more. Season chili with salt and pepper. Tilt pot and spoon off any fat from surface of sauce.

Ladle chili into bowls and serve topped with fresh cilantro leaves, chopped red onion, pickled jalapeños, diced avocado, shredded Monterey Jack or cheddar cheese, and warm corn and/or flour tortillas (if using). Do Ahead: Chili can be made 2 days ahead. Let cool 1 hour. Chill uncovered until cold, then cover and keep chilled. Reheat on low. Editor’s note: This Texas chili recipe was first printed in our October 2008 issue as Texas Beef Brisket Chili. Head this way for more of our top Super Bowl recipes →