The Best Slow Cooker Steak Chili You’ve Ever Eaten

Prep Time:45 mins
Cook Time: 6 hrs
Total Time: About 7 hrs
Servings: 8-10

1/4 cup chili powder
2 Tablespoons whole cumin seeds
1/4 teaspoon cayenne pepper
1/2 teaspoon ground cinnamon
2 teaspoons dried Mexican or regular oregano
3 bay leaves
2 teaspoons brown sugar
4 pounds steak, cut into 1-inch cubes (can also use boneless chuck or stew meat)
1 teaspoon freshly ground black pepper
2 1/2 Tablespoons Kosher salt
3 Tablesoons heat-safe oil (coconut or grapeseed)
4 cups chopped onions (3 medium or 2 large)
1 1/2 cups chopped celery (about 4 ribs)
6 cloves garlic, chopped
2 jalapeno chiles, seeded and roughly chopped
1 1/2 cups stock (beef, chicken, or vegetable will do)
2 Tablespoons tomato paste
1 28-ounce can crushed tomatoes
1 ounce semisweet chocolate chips
3 Tablespoons masa harina (corn flour, not cornstarch)
2 cups water
2 cups chopped butternut squash (optional)
1/2 cup chopped cilantro
1/2 cup chopped parsley
Grated cheddar, chopped green onions, and sour cream for garnish

Combine the first 7 ingredients in a small bowl and set aside.
Add the beef to a large bowl and season with the black pepper and 1 Tablespoon of the salt.
Heat the oil in a large, deep skillet or saute pan over high heat. Add about 1/3 of the beef to the skillet. Let the meat sit for a minute or so, then stir them up. Cook for another couple of minutes, then transfer the meat to the crock of a 6-quart slow cooker. Repeat with remaining beef, adding it to the skillet in two more batches and browning them in spots. Add more oil between batches, if necessary.
When you're finished with the beef, add the onion, celery, and 1 Tablespoon of the remaining salt to the skillet and cook, stirring, until the vegetables begin to soften, about 2 minutes. Add garlic, jalapenos, and spice mixture and cook for another minute. Pour in the stock, tomato paste, and crushed tomatoes and simmer for 3 minutes. Stir in the chocolate, masa harina, and another couple large pinches of salt and cook for another minute. Transfer this mixture to the slow cooker with the beef. Add the water and the squash cubes (if using).
Cover and cook on high for 6 hours, stirring only once or twice, until the beef is very tender. Remove the bay leaves and stir in the cilantro and parsley. Serve the chili with garnishes.

Slow Cooker Taste