Using a sharp knife, slice off the base of the radicchio heads (about 1/2 inch). Carefully pull the individual leaves apart and submerge in a large bowl of ice water for about 10 minutes. Remove from the water and dry thoroughly.
While the radicchio is soaking, add the sliced shallot rounds to a small bowl with 3 tbsp red wine vinegar. Let soak until needed later on.
To a medium bowl or measuring cup, add 1/2 cup olive oil. Strain the red wine vinegar into the bowl, and set aside the pickled shallots. Add 1 tbsp honey and 1/2 tbsp dijon mustard along with a pinch of salt and a few cracks of black pepper. Optionally, add a squeeze of juice from the leftover blood orange carcass. Whisk thoroughly until fully emulsified.
In a large mixing bowl, add the dry radicchio leaves, the pickled shallots, pitted olives, and the dressing. Using tongs or clean hands, toss to combine.
Serve salad on a large platter or individual plates. Garnish with the blood orange wedges, shaved or grated parmesan cheese, and a few cracks of black pepper.