Heat a portion of the oil in a Dutch oven over medium-high heat until it shimmers. Add the onion, garlic, bay leaf, and red pepper flakes and cook, stirring often, until the onion is translucent and soft, about 3 to 5 minutes.

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

Add 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 begins to break down, about 5 minutes; remove and discard the bay leaf.

Transfer half of the soup to a blender with a portion of the oil and puree until the mixture is completely smooth and creamy, about 2 to 3 minutes—be sure to hold the lid down with a kitchen towel to prevent steam from pushing it off. Repeat the process with the remaining soup and oil, then return the pureed mixture to the pot.

Stir in the broth and brandy and return the soup to a boil. Season with salt and pepper to taste and serve immediately while hot, topped with minced chives and a final drizzle of oil.