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Preheat a grill to medium-high heat.
In a large bowl, toss chicken breast pieces with olive oil, Italian seasoning, granulated garlic, crushed red pepper flakes, 1 teaspoon salt and 1/2 teaspoon pepper.
Stack two pepperonis on top of each other and then fold them in half. Thread the skewers with the folded pepperoni first then a piece of chicken, alternating until there are three cubes of chicken on each skewer with two folded pepperoni stack in between each one and ending with pepperoni.
Place the skewers onto the grill and cook for 4 minutes per side or until the chicken is cooked through.
Place the skewers onto a platter and stick a banana pepper on the end of each skewer. Serve with pesto alongside for dipping.
Party tip: The skewers can be assembled and refrigerated up to two days ahead of time.