Brisket and Winter Squash Chili

Brisket and Winter Squash Chili

Serving Size: Makes 8 servings


    For the chili:
  • 3 oz dried ancho chiles, stemmed, seeded, coarsely torn
  • 6 ounces beef bacon, diced
  • 1 large vidalia onion (1lb), diced
  • 4 lb beef brisket, fat trimmed, cut into 2 inch cubes and seasoned with salt and pepper
  • 6 large garlic cloves
  • 3-4 canned chipotle chilies in adobo (& 1 tbsp juice)
  • 2 tbsp chili powder
  • 1 tbsp ground cumin
  • 1 tsp dried oregano
  • 1 tsp ground coriander
  • 2 tsp salt
  • 1 12oz bottle Mexican beer
  • 1 7-ounce can diced roasted green chiles
  • 3 10oz cans fire-roasted diced tomatoes with chipotle
  • 1/2 cup finely chopped fresh cilantro stems
  • 4 cups cubed butternut squash (from a 2 pound squash)
  • For Garnish:
  • Sliced avocado (doused in lime juice to prevent browning, and add flavor)
  • Shredded sharp white cheddar cheese
  • Sour cream


  1. Preheat the oven to 350 degrees.
  2. In a medium bowl, pour boiling water over the ancho chiles to rehydrate them. If they float to the surface, use a small bowl to submerge them. Set aside.
  3. In a large oven-proof Dutch oven, heat 1-2 tablespoons of olive oil over medium-high heat. Saute the bacon until browned all over. Turn the heat down to medium, add the onions and continue to sauté until tender. Stir in the beef and return the heat to high.
  4. While the beef cooks, at the garlic, ancho chiles, chipotle chiles, and 1 cup of the soaking liquid to a small food processor. Blend until smooth.
  5. To the pot, add the chili mixture and the spices (chili powder, cumin, oregano, coriander, salt) and toss to coat. Cook for a few minutes until very fragrant, and then add the beer, green chiles, 2 cans of tomatoes, and cilantro stems. Bring the chili to simmer.
  6. Cover the pot and place it in oven. Cook 2 hours. Uncover and cook until beef is almost tender, about 1 hour. Stir in the pumpkin, and the remaining can of tomatoes and return to the oven. Cook uncovered until beef and pumpkin are tender, about 1 hour longer. Tilt pot and spoon off any fat from surface of sauce.
  7. Taste for seasoning, and serve with a dollop of sour cream, a slice of avocado, and a sprinkle of cheese.

instagram  If you make this, share a photo and tag me @PhoebeLapine #feedmephoebe - I would love to see it!


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