3 Tbsp Olive Oil, divided
1-1/2 lbs boneless short ribs, trimmed and cut into 1/2-in cubes
3/4 tsp Salt
1-1/2 Cups chopped onion
1 Tbsp minced fresh garlic
1 tsp chipotle chile in adobo (canned), finely minced
2 Tbsp tomato paste
1-1/2 tsp Ground Ancho Chile Pepper
1 tsp unsweetened Cocoa Powder
1/2 tsp Ground Cumin
1/8 tsp Ground Cinnamon
2/3 Cup dry red wine
1 (28-oz) can whole tomatoes, chopped and liquid reserved
1 (15-oz) can black beans, drained and rinsed
2 Cups butternut squash, peeled, seeded and cut into 1/2″ cubes
2 Tbsp fresh cilantro
1/4 Cup 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 1 Tbsp of the olive oil as the pan heats. Lightly salt the beef, then add to oiled pot. Saute beef, stirring frequently, until pieces are browned on all sides (about 8 min). 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 min, 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.
Adapted from Cooking Light magazine