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Preheat the oven to 350°F.
Use a small sharp knife to cut a pouch or cavity in the thickest part of each chicken breast. Set aside.
Brush olive oil all over the chicken breast, including the cavity. Sprinkle the chicken all over (including inside the cavity) with salt, pepper, oregano, and basil. Sprinkle the minced garlic in the cavity of each breast.
Sprinkle a little salt and pepper on the tomato slices. Fill each cavity with a couple of tomato slices, mozzarella slices, and a couple of chopped basil leaves. You may need to cut the slices in half in order for it all to fit.
Use your fingers to squeeze the cavity closed and then use 4 to 5 toothpicks the close up the chicken breast.
Heat 1 tbsp olive oil in a large cast-iron skillet or Dutch oven over medium-high heat. Carefully transfer the stuffed breasts to the skillet. Sear one side for about 4 minutes, until browned on the bottom. Again, carefully flip the breasts over and sear for another 4 minutes.
In a small jar, mix together the balsamic, brown sugar, and chicken broth. Pour the balsamic mixture all over the chicken. Use a spoon to coat the tops of the chicken with the sauce.
Place the skillet in the oven for 15 to 20 minutes, or until an internal temperature reaches 165°F. Serve at once with sauce poured over the tops of the chicken and extra sauce at the table.