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If half of the soup fills your blender by more than two-thirds, process the soup in three batches. You can also use an immersion blender to process the soup directly in the pot. For an even smoother soup, pass the pureed mixture through a fine-mesh strainer before stirring in the chicken broth in step 2.
- 1⁄4 cup extra virgin olive oil, plus extra for drizzling
- 1 medium onion, chopped (about 1 cup)
- 3 medium garlic cloves, minced-pressed
- 1 pinch hot red pepper flakes
- 1 bay leaf
- 2 (28 ounce) canswhole tomatoes with juice
- 1 tablespoon brown sugar
- 3 large slice good-quality white bread, crusts removed, torn into 1-inch pieces
- 2 cups chicken broth or 2 cups vegetable broth
- 2 tablespoons brandy (optional)
- salt and pepper
- 1⁄4 cup fresh chives, chopped
- Heat 2 tablespoons oil in Dutch oven over medium-high heat until shimmering. Add onion, garlic, red pepper flakes, and bay leaf. Cook, stirring frequently, until onion is translucent, 3 to 5 minutes.
- Stir in tomatoes and their juice. Using a potato masher, mash until no pieces bigger than 2 inches remain. Stir in sugar and bread; bring soup to a boil. Reduce heat to medium and cook, stirring occasionally, until bread is completely saturated and starts to break down, about 5 minutes. Remove bay leaf and discard.
- Transfer half of soup to a blender, add 1tablespoon olive oil and process until soup is smooth and creamy, 2 to 3 minutes. Be extra careful when putting hot liquids in the blender. Never fill past 2/3 of the way full, and put a dish towel over the top just in case to protect your hands from getting burned by any hot liquid splashing up. Transfer to a large bowl and repeat with remaining soup and oil.
- Rinse out Dutch oven and return soup to pot. Stir in chicken broth and brandy. Return soup to a boil and season to taste with salt and pepper.
- Sprinkle each portion with pepper and chives and drizzle with olive oil. Serve (of course) with grilled cheese sandwiches.