Heat the oil in a Dutch oven over medium-high heat until it shimmers but does not smoke. Add the onion, garlic, bay leaf, and pepper flakes and cook, stirring often, until the onion is translucent and soft, 3 to 5 minutes.

Stir in the tomatoes and their juice. Use a potato masher to break the tomatoes apart until no pieces larger than 2 inches remain.

Stir in the bread and sugar and bring the soup to a boil. Reduce the heat to medium and cook, stirring occasionally, until the bread is completely saturated and starts to break down, about 5 minutes. Remove and discard the bay leaf.

Transfer half of the soup to a blender and add the oil. Puree until the soup is completely smooth and creamy, 2 to 3 minutes. Transfer to a bowl and repeat the process with the remaining soup and remaining oil.

Return the pureed soup to a clean pot and stir in the broth and brandy. Return the soup to a boil and season with salt and pepper to taste.

Serve hot in warmed bowls, finished with a sprinkle of chives and a generous drizzle of oil.