Lay the prosciutto on a parchment-lined sheet tray. Bake until darkened and crispy, 10 to 12 minutes. Allow to cool fully, and then break up the prosciutto into pieces. Set aside.
Heat 2 ounces (1/8 cup) olive oil in a large saute pan over medium heat. Add half of the bread and let cook until the underside begins to brown, about 3 minutes, then flip the bread and finish the other side, about 3 minutes more. Sprinkle with salt and pepper. Remove from the pan and rub both sides with a garlic clove to perfume the toast. Wipe out the pan and repeat again with the remaining oil and bread.
Place the chopped tomatoes in a medium bowl. Grate the remaining clove garlic on a fine grater into the tomatoes. Add the basil, olives and half the Parmesan. Season with salt and pepper. Arrange the bread on a serving platter. Top the toasted garlic bread with the tomato mixture, then top with the crispy prosciutto pieces. Sprinkle with the remaining Parmesan.