Heat a cast-iron fry pan or griddle on medium heat. Cook the bacon and allow to drain on paper towels.
Preheat the oven to 350 degrees F.
Cut the tomato in half, season with salt and pepper and roast in the oven on a baking sheet, face down, until it is soft to the touch, about 10 minutes. Chop the tomato.
Mix the 2 cheeses together evenly in a bowl. Butter the outsides of the bread. Press half of the grated cheese on each bottom piece of bread. Crumble half the bacon and half the chopped roasted tomato on each sandwich. Place the top half of the bread on the cheese mixture with the buttered side up.
Preheat a cast-iron fry pan or griddle over medium heat. To cook, place the sandwich in the fry pan. Flip it over with a pancake spatula when the bread is browned and the cheese is partially melted. Be patient, this should take at least 5 minutes. When the second side is browned and the cheese properly melted, remove from the pan. Lift the top half up and place arugula leaves in the sandwich.
Serve with the pickles of your choice.
This recipe was provided by a chef, restaurant or culinary professional and may have been scaled down from a bulk recipe. The Food Network Kitchens chefs have not tested this recipe, in the proportions indicated, and therefore, we cannot make any representation as to the results.