Vinter Panzanella

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1. 1
   Place a rack in middle of oven; preheat to 400°. Place 8 oz. pumpernickel or other hearty brown bread (such as rye or whole wheat), coarsely torn (about 4 cups), on a rimmed baking sheet, drizzle ⅓ cup extra-virgin olive oil over, and season with ½ tsp. Diamond Crystal or ¼ tsp. Morton kosher salt and ½ tsp. freshly ground pepper. Lightly massage with your hands to help bread absorb all of the oil. Bake until bread is dried out and fragrant, 13–17 minutes. Let croutons cool on baking sheet; set aside.
2. 2
   Meanwhile, using a paring knife, remove peel and white pith from 4 medium oranges, taking care not to remove too much flesh. Cut oranges into 1" pieces, leaving center pithy parts behind; set orange pieces aside. Squeeze juice from scraps into a liquid measuring cup, then discard. Cut remaining 1–2 medium oranges in half and squeeze in juice through a mesh sieve to get to ½ cup; discard seeds.
3. 3
   Add 2 garlic cloves, finely grated, ½ cup plus 2 Tbsp. balsamic vinegar, 2 Tbsp. Dijon mustard, 1 tsp. Diamond Crystal or ½ tsp. Morton kosher salt, ½ tsp. freshly ground pepper, and remaining ⅓ cup extra-virgin olive oil to orange juice and whisk to combine. Taste dressing and season with more salt and pepper if needed.
4. 4
   Toss ½ large fennel bulb, cut into quarters through root end, thinly sliced lengthwise, 3 large shallots, thinly sliced, 8 oz. mixed chicories (such as radicchio and/or endive), leaves separated, torn into very large pieces if needed (about 6 cups), and reserved orange pieces and croutons in a large bowl. Using a vegetable peeler, shave 2 oz. Parmesan into bowl. Drizzle about half of dressing over and toss to coat. Let sit 3 minutes to absorb. Drizzle with more dressing if bread seems dry (it should be pleasantly soggy but not falling apart); season with more salt and pepper if needed.
5. 5
   Arrange panzanella on a platter and top with more shaved Parmesan.