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. Serve this soup with Grilled Cheese Sandwiches for a Crowd or topped with Butter Croutons (see related recipes).
1. Heat 2 tablespoons oil in Dutch oven over medium-high heat until shimmering. Add onion, garlic, red pepper flakes (if using), and bay leaf. Cook, stirring frequently, until onion is translucent, 3 to 5 minutes. Stir in tomatoes and their juice. Using potato masher, mash until no pieces bigger than 2 inches remain. Stir in sugar and bread; bring soup to boil. Reduce heat to medium and cook, stirring occasionally, until bread is completely saturated and starts to break down, about 5 minutes. Remove and discard bay leaf.
2. Transfer half of soup to blender. Add 1 tablespoon oil and process until soup is smooth and creamy, 2 to 3 minutes. Transfer to large bowl and repeat with remaining soup and oil. Rinse out Dutch oven and return soup to pot. Stir in chicken broth and brandy (if using). Return soup to boil and season to taste with salt and pepper. Serve soup in individual bowls. Sprinkle each portion with pepper and chives and drizzle with olive oil.