Heat 3 tablespoons olive oil in a heavy-bottomed pot or Dutch oven over medium-high heat. Season 2 ½ - 3 pounds chuck roast cut into ½-inch cubes with 2 teaspoons salt and 1 teaspoon pepper.
Add the beef in batches, browning the meat on all sides. 5-6 minutes per batch. Remove the browned meat and set aside.
To the same pot, add 1 large diced yellow onion, 2 jalapeno peppers, seeded and diced, and 6 minced garlic cloves. Cook, stirring occasionally until softened; this will take 4-5 minutes.
Add 2 tablespoons chili powder, 1 tablespoon smoked paprika, 1 tablespoon cumin, 1 tablespoon brown sugar, 2 teaspoons dried oregano, 1 teaspoon coriander, ½ tablespoon cocoa powder, 2 chopped chipotles in adobo, and 1 tablespoon tomato paste. Stir to combine.
Add the beef back to the pot, then add 1 (28-ounce) can crushed tomatoesand 4 cups beef broth. Stir to combine.
Bring to a boil, then reduce the heat to low. Cover the pot and simmer for 2-3 hours, stirring occasionally, until the meat is tender and the chili has thickened. If the chili gets too thick, add more broth as needed.
Notes
Storing Leftovers
Refrigerator: Store in an airtight container for 4–5 days.
Freezer: Freeze in an airtight container for up to 3 months. Thaw overnight in the fridge before reheating.
Reheating: Warm on the stovetop or in the microwave until hot and simmering. If it’s too thick, stir in a splash of broth or water.