- To a large pot over medium-high heat, add oil.  
- Once the oil is hot, add the chopped onion and garlic. Cook, stirring frequently, until the onion is translucent, about 3 to 5 minutes. 
- Stir in the tomatoes and their juice. Using a potato masher, mash until no pieces bigger than two inches remain. 
- Stir in brown sugar and bread; bring soup to a boil, stirring occasionally, until the bread is completely saturated and starts to break down, about 5 minutes. Reduce heat to medium. 
- Transfer half of soup to a blender. (Or use your immersion blender and leave everything in the pot.) 
- Add one tablespoon oil and process until soup is smooth and creamy, 2 to 3 minutes. Transfer to large bowl and repeat with remaining soup and oil. 
- Return the soup to the pot and add two cups of chicken broth, or enough to reach your desired consistency. 
- Season to taste with salt and pepper.