In a 6- to 8-quart Dutch oven, brown beef cubes, on all sides, in hot oil. Remove beef cubes and place in a large bowl; reserve pan drippings. Add ground beef and Italian sausage to reserved drippings. Cook meats until brown, stirring occasionally. Transfer ground beef and the Italian sausage to the same bowl with beef cubes. Drain pan drippings, reserving 2 tablespoons in the Dutch oven.
Add onions and sweet peppers. Cook and stir over medium heat about 10 minutes or until onion is tender. Remove pan from heat. Add wine to onion mixture in pan. Return to heat. Bring to boiling; reduce heat. Simmer, uncovered, about 5 minutes or until wine is reduced by about half. Stir in undrained stewed tomatoes, tomato sauce, water, brown sugar, cumin, chili powder, Aleppo Pepper, tomato paste, salt, Black Telllicherry Pepper and bay leaves. Bring to boiling.
Add meat mixture to tomato mixture. Return to boiling; reduce heat. Simmer, covered, for 3 hours, stirring occasionally. Add beans to meat mixture and cook for 30 minutes more. If using whole bay leaves, remove and discard.
To serve, ladle the chili into soup bowls. Top each with cheddar cheese, cilantro, and, if desired, Tortilla Strips. Makes 10 (1-1/2-cup) servings.
Set a large wire cooling rack over a paper towel-lined baking sheet; set aside. Halve ten 6-inch yellow corn tortillas, the cut crosswise into 1/2-inch-wide strips. In a heavy large saucepan, heat 1/2-inch of cooking oil over medium-high heat. Add the tortilla strips, a few at a time, and cook for 45 to 60 seconds or until crisp and lightly browned. Using a slotted spoon, remove the tortilla strips from the hot oil. Transfer to cooling rack; drain well. Repeat with remaining tortilla strips. Makes about 5 cups.