Ancho Macho Chili

5 pounds boneless beef chuck stew meat
2 teaspoons kosher salt
1/2 teaspoon freshly ground black pepper
3 tablespoons olive oil or vegetable oil, divided
1 medium onion, chopped
3 tablespoons ancho chile pepper powder or Mexican-style chili powder
1 (14.5 ounce) can diced tomatoes with green chiles
3/4 cup dry red wine or chicken broth
4 large roasted garlic cloves, minced
Heat oven to 325F. Toss beef with salt and pepper. Heat 1 1/2 teaspoons oil in a Dutch oven over high heat. Add one-third of the beef and brown on all sides, about 5 minutes. Transfer to a bowl and repeat two more times with beef and oil.
Add the last 1 1/2 teaspoons oil to Dutch oven and cook onion until lightly browned. Stir in chile powder, tomatoes, wine and garlic; bring to a simmer. Return beef and accumulated juices to Dutch oven. Cover and bake 2 1/2 hours, stirring once halfway through cooking time, until beef is very tender.
 
Servings: 8