Preheat the oven to 350°F. Pour the oil into a large skillet set over medium heat. Add the peppers and olives and cook until they begin to soften, about 5 minutes. Add the pork and continue cooking until the pork is warmed through. Add the cheese and stir until it melts. Remove from heat.
Spray a muffin pan with nonstick cooking spray. Lay one wonton wrapper over each cup of the muffin pan and then lay another wonton wrapper on top, but set slightly offset to form a star pattern. Place one tablespoon of the meat and cheese mixture in the center and gently push down into the muffin cup. Repeat until all of the muffin cups are full.
Bake until the edges of the wonton are browned and slightly crispy, about 20 minutes. Remove from the oven and season to taste with dry rub. Let cool and enjoy.