Heat 2 tablespoons oil in a large pot over medium heat until shimmering.
Add onion, garlic, bay leaf, and pepper flakes(if using). Cook, stirring often, until onion is translucent, 3 to 5 mins.
Stir in tomatoes and their juice. Mash the tomatoes with a potato masher until no pieces bigger than 2 inches remains,
Stir in bread and sugar and bring soup to boil.
Reduce heat to medium and cook while stirring occasionally, until the bread is completely saturated and starts to break down.
Discard the bay leaf and transfer half of soup to blender.
Add 1 tablespoon oil and puree until soup is smooth and creamy. Transfer to large bowl and repeat with remaining soup and remaining 1 tablespoon oil.
Return pureed soup to clean pot, let it come to boil and season with salt and pepper to taste.
Drizzle oil and sprinkle some chives while serving.
Best served with grilled cheese!