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.
Make the dressing
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.
Assemble the salad
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.