Preheat the oven broiler on low.
In a bowl mix the oil (reserve 1/3 for cooking the turkey), garlic, oregano and season with salt and pepper. Brush the mixture on both halves of the bread to coat completely. Place under the broiler until golden brown and still soft. Then set aside and place the cheese on the top of the sub roll.
In a bowl mix the ground turkey, Montreal seasoning, paprika, salt, and pepper. Form into oolong patties to fit the sub roll.
Heat a sauté pan on medium heat. Once hot, add the oil. Cook the turkey patties on both sides to an internal temperature of 160 degrees using a thermometer.
Spread the cherry pepper spread onto the bottom half of the sub roll, layer with arugula, tomato, and turkey patty.
Cut the sandwich in half and serve with chips and pickles.