- 3 Tbsp. Extra Virgin Olive Oil, Unflavored, Divided
- 1½ lbs. Boneless Short Ribs, Trimmed and Cut into ½” cubes
- ¾ tsp. Kosher Salt
- 1½ C. Chopped Onion
- 1 Tbsp. Minced Fresh Garlic
- 1 tsp. Chipotle Chile in Adobo, Finely Minced
- 2 Tbsp. Tomato Paste
- 1½ tsp. Ancho Chile, Crushed
- 1 tsp. Organic Cocoa Powder, Dutch Processed
- ½ tsp. Cumin, Ground
- 1/8 tsp. Cinnamon, Saigon Ground
- ⅔ C. Dry Red Wine
- 28-oz. Can Whole Tomatoes, Chopped and Liquid Reserved
- 15-oz. Can Black Beans, Drained and Rinsed
- 2 C. Butternut Squash, Peeled, Seeded and Cut into ½”cubes
- 2 Tbsp. Fresh Cilantro
- ¼ C. Cotija Cheese, Crumbled
- Coat a large, heavy pot or Dutch oven with non-stick cooking spray and place on stove over medium-high heat. Add one tablespoon of the olive oil as the pan heats.
- Lightly salt the beef, then add to oiled pot. Sauté beef, stirring frequently, until pieces are browned on all sides (about 8 minutes). Transfer browned beef to a bowl and set aside.
- Add remaining olive oil to Dutch oven, along with the onion. Reduce heat to medium and sauté the onion for an additional 8 minutes, or until nearly translucent, before adding garlic and sautéing for one more minute. Add the tomato paste, chipotle-in-adobo, and spices to onion-garlic mixture, and heat for 2-3 minutes, stirring continuously.
- Add red wine to the tomato-onion mixture and turn up the heat slightly. Stir mixture to combine, and use a spatula to scrape any browned bits of garlic and onion from edges of pan. Bring mixture to a boil, then return browned beef to the pan. Add tomatoes and beans, and once mixture bubbles again, cover the pan and reduce heat to a simmer. Allow to simmer, undisturbed, for one hour.
- After the beef has simmered for an hour, add the butternut squash cubes, replacing the lid and letting the chili bubble awhile longer. When butternut squash pieces are fork-tender, and beef chunks are tender, too, the chili is ready.
- Garnish with a generous tablespoon of Cotija cheese and a sprinkle of fresh cilantro.
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