¼ cup extra virgin olive oil, divided, plus more for drizzling
1 medium onion, chopped (about 1 cup)
3 medium garlic cloves, minced or pressed through garlic press (about 1 tablespoon)
Pinch hot red pepper flakes (optional)
1 bay leaf
2 (28-ounce) cans whole tomatoes in juice
1 tablespoon brown sugar
3 large slices good-quality sandwich bread, crusts removed, torn into 1-inch pieces
2 cups low-sodium chicken or vegetable broth
2 tablespoons brandy (optional)
¼ cup chopped fresh chives
Croutons, for serving
In a Dutch oven set over medium-high heat, heat 2 tablespoons of oil until shimmering. Add onion, garlic, red pepper flakes (if using) and bay leaf. Cook for 3-5 minutes, stirring occasionally, until onion is translucent. Add tomatoes and their juices. Mash tomatoes using a potato masher, until tomato pieces are all smaller than 2 inches. Add sugar and bread.
Increase heat to high and bring soup to a boil. Once boiling, reduce heat to medium and and cook, stirring occasionally, until bread is completely saturated and beginning to disintegrate, about 5 minutes.
Remove bay leaf, add remaining 2 tablespoons of oil and use an immersion blender to blend the soup until smooth. Stir in broth and brandy (if using). Alternately, transfer half of soup to a blender and add 1 tablespoon of oil. Blend for 2-3 minutes, or until smooth and creamy. Transfer to a large bowl and repeat with remaining soup and 1 tablespoon of oil.
Return soup to pot and stir in broth and brandy (if using). Season to taste with salt and pepper and return to a boil. Sprinkle chives over the top of each serving of soup and drizzle with additional olive oil, if desired. Top with croutons.