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Step 1
Preheat oven to 350 degrees F.
Step 2
Roast Garlic for Dressing: Cut ends of garlic heads off with a serrated knife exposing individual tips of garlic cloves. Place root-side down in a small baking dish and drizzle with 2 tablspoons oil over the exposed garlic clove ends. Cover with foil and transfer to the oven. Roast garlic until the garlic is soft and fragrant and starting to brown, 1 hour to 1 hour 25 minutes. Remove foil and allow garlic to cool.
Step 3
Make Croutons: Lay baguette on a parchment lined baking sheet. Stir 1 tablespoon oil, Italian seasoning and salt in a small dish. Brush oil over the baguette slices. Bake until browned and crisp, 14 to 16 minutes. Cool.
Step 4
While croutons cool, make dressing: Squeeze cloves from two heads of garlic into a blender or food processor and discard papery skins. Add roasted garlic oil from the baking dish, if there is any. Add the remaining ¼ cup oil, lemon juice, capers, anchovy paste, mustard and pepper and puree until smooth. Add grated Parmigiano-Reggiano and puree to combine.
Step 5
Make Salad: Combine romaine, raddichio and grated Parmigiano or Asiago in a large salad bowl. Pour dressing over the salad and toss to combine. Mound onto 6 plates and serve each with three croutons and a head of garlic.