3 tablespoons olive oil or butter
1 onion, medium or large
1 and 1/2 teaspoons kosher salt
1/2 teaspoon black pepper
1/4 teaspoon red pepper flakes, or to taste
1 tablespoon dried oregano
1/2 teaspoon dried basil
3 cloves garlic, smashed and minced
1 (28 ounce) can whole tomatoes*
1 (15 ounce) can fire-roasted diced tomatoes
4 cups chicken broth**
1/2 to 1 cup cream
1/2 cup fresh basil, chopped
Heat a large soup pot over medium high heat. Add the oil or butter. When the oil shimmers (or the butter melts), add 1 chopped onion.
Season with 1 and 1/2 teaspoons kosher salt, 1/2 teaspoon black pepper, 1/4 teaspoon red pepper flakes, 1 tablespoon dried oregano, and 1/2 teaspoon dried basil.
Saute until the onions are lightly browned, 5-8 minutes.
Add 3 cloves of minced garlic (about a tablespoon) and saute for 1 more minute.
Add the can of whole tomatoes (with juices) and the can of diced tomatoes (with juices). Add 4 cups chicken broth.
Turn the heat up to high and bring the mixture to a boil. Once it boils, turn the heat down to a low simmer and cook for at least 10 minutes, or up to 45 minutes if you have the time.
Turn off the heat and use an immersion blender to puree the soup. If you do not have an immersion blender (why, why??) then let the soup cool for a couple minutes before transferring to a blender. You will have to do it in a few batches. Do not fill the blender to the fill line; add less than you think. The soup is very hot and will expand when blended, which could overflow your blender and splatter you with molten hot lava tomato soup. The other thing I recommend is to take out the little spout at the top of the blender and hold a towel over the top of the lid while blending. This will allow steam to escape and you will be able to avoid tomato soup Pompeii.
Once all the soup is blended, heat it back up again on the stove if necessary. Turn off the heat and slowly stir in 1/2 to 1 cup cream.
If you want, chop up about 1/2 cup basil and stir it into the soup, or top each serving with fresh basil.
Serve warm with grilled cheese sandwiches! If you want you can cut sandwiches into tiny “croutons” and put them in your soup like in the photos. But…they get soggy pretty much right away. So unless you are taking photos of your soup to put on the internet, I say just dip your sandwich!