Heat 2 teaspoons of olive oil in a large skillet over medium heat. Add the diced red bell pepper and onion. Sauté until they are softened, about 5 minutes. Add the minced garlic and cook for an additional minute until fragrant.
Stir in the shredded chicken, sliced black olives, roasted corn, and minced chipotle pepper (or jalapeno). Cook for another 2-3 minutes until everything is heated through and well combined. Remove the mixture from the skillet and set it aside.
Place a tortilla in the same skillet over medium heat. Sprinkle half of the tortilla with a layer of shredded Monterey jack cheese, then add a generous scoop of the chicken and vegetable mixture on top. Finally, add another layer of cheese before folding the tortilla in half.
Cook the folded quesadilla for about 3-4 minutes on one side until golden brown and crispy. Carefully flip it over and cook for another 3-4 minutes until the other side is browned and the cheese is melted.
Repeat the process with the remaining tortillas and filling. Once cooked, slice the quesadillas into wedges and sprinkle with fresh cilantro. Serve hot with your favorite dipping sauce, such as salsa or guacamole.
