Preheat oven to 400 degrees F. Line a baking sheet with parchment paper and set aside. Cut each radicchio in half from top to bottom. Cut each half into 3 wedges and lay on prepared baking sheet. Drizzle with olive oil and a large pinch of salt and pepper, and gently toss to coat in oil. Roast for 25 minutes or until browning. Remove from oven and set aside.

Add balsamic vinegar to a small skillet over high heat and bring to a boil. Reduce heat to low and cook for 25 to 30 minutes or until vinegar has thickened and reduced to 2 tablespoons. Pour into a small bowl and whisk in olive oil and a pinch of salt. Set aside.

Place 3 wedges of roasted radicchio on each of 4 plates. Divide Parmesan and pomegranate seeds over the radicchio and drizzle each salad with a tablespoon of dressing. Top with cracked pepper and serve.