Preheat the grill.
Season both sides of the eggplant slices with olive oil, salt, and pepper. Grill the eggplant for 2 minutes on each side.
Lay a piece of prosciutto on one piece of grilled eggplant. Lay a slice of cheese on top of the prosciutto. Carefully roll up the eggplant and secure the roll with two toothpicks. Repeat the above process with the remaining grilled eggplant.
Cut the radicchio in quarters. Toss with olive oil, salt and pepper. Grill for 1 minute on each side. Remove from the grill and cut away the core of the lettuce. Using a sharp knife, shred the radicchio. In a mixing bowl, toss the radicchio with extra-virgin olive oil, salt, and pepper. Set aside.
Place the eggplant roulades on the grill and cook until the cheese starts to melt. Remove from the grill. Place the radicchio on a large platter. Arrange the roulades on the platter. Drizzle the entire platter with the Balsamic Syrup.
In a medium-saucepan, over medium heat, add the balsamic vinegar. Bring to a boil and reduce to a simmer. Simmer until the liquid reduces by 3/4, about 30 minutes or until syrup-like consistency. Remove from the heat and cool completely.