1Heat closed medium-size contact grill for 5 minutes. Place bacon crosswise on grill. Close grill. Grill 5 to 6 minutes or until crisp. Remove from grill; drain on paper towels. Scrape drippings from grill. Coarsely chop bacon.
2Sprinkle 4 tortillas with cheese. Top each with bacon, chiles, sliced olives, onion and remaining tortillas; press lightly.
3Place 1 quesadilla at a time on grill. Close grill. Grill 2 to 4 minutes or until light golden brown and cheese is melted. Cut each quesadilla into 4 wedges. Attach tomato or whole olive to top of each wedge with decorative toothpick.