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1
Spray Dutch oven with cooking spray and heat 2 teaspoons oil over medium heat until shimmering.
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2
Add onion, garlic, red pepper flakes (if using), and bay leaf.
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3
Cook, stirring frequently, until onion is translucent, 3 to 5 minutes.
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4
Stir in tomatoes and their juice.
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5
Using potato masher, mash until no pieces bigger than 2 inches remain.
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6
Stir in sugar and bread; bring soup to boil.
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7
Reduce heat to medium and cook, stirring occasionally, until bread is completely saturated and starts to break down, about 5 minutes.
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8
Remove and discard bay leaf.
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9
Transfer half of soup to blender. (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.).
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10
Add 1 teaspoon oil and process until soup is smooth and creamy, 2 to 3 minutes.
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11
Transfer to large bowl and repeat with remaining soup and oil.
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12
(For an even smoother soup, pass the pureed mixture through a fine-mesh strainer before stirring in the chicken broth.).
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13
Rinse out Dutch oven and return soup to pot and heat to a simmer.
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14
Stir in chicken broth and brandy (if using) and bring to a simmer.
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15
Season to taste with salt and pepper.
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16
Serve soup in individual bowls.
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17
Sprinkle each portion with pepper and chives.
