2 pounds chuck roast, cut into 2-3 steaks
Salt and freshly ground pepper, to taste
2 tablespoons olive oil
4 ounces bacon, chopped
2 large onions, sliced
4 cloves garlic, minced
1 teaspoon cumin
2 teaspoons dried oregano
1/2 teaspoon cinnamon
3 teaspoons chili powder
2 teaspoons chipotle powder
2 cups stout beer
1 cup beef broth
1 (15 ounces) can crushed tomatoes
1 tablespoon tomato paste
1 - 2 tablespoons brown sugar (optional or to taste)
1 tablespoon unsweetened cocoa powder
2 ounces dark or semisweet chocolate, chopped
1 bay leaf
2 tablespoons balsamic vinegar
Season steaks generously with salt and pepper. Heat oil in a large Dutch oven, over medium high heat, until shimmering. Add the steaks and brown for 4-5 minutes per side. Remove and reserve.
Lower the heat to medium and add the bacon. Cook until it begins to brown, about 4 minutes. Add the onions and sauté until they begin to brown, 7-8 minutes. Then, add the garlic and cook for a minute or so, until fragrant.
Cut the seared steaks into small chunks (about 1/4-inch thick) and add them back to the pot. Add the spices and cook for a minute to release its flavors.
Add the stout, broth, tomatoes, tomato paste, brown sugar, cocoa powder, chopped chocolate, bay leaf and a pinch of salt and pepper.
Lower the heat to a simmer and cook for at least 1 hour, or until the meat is tender and the chili is rich and thick. You can add more broth, as needed, if the chili gets too thick.
When done, stir the balsamic vinegar. Taste and adjust salt and pepper, if necessary.