preheat oven to 400 degrees

• Wash and dry tomatoes. Drizzle 1 tablespoon of olive oil on baking sheet. Cut roma tomatoes in half place on sheet. Smash garlic and remove skins place on sheet with tomatoes. Remove outer skin of shallot and slice add to pan. Drizzle with 1 tablespoon of olive oil and sprinkle with salt and pepper. Place baking sheet in oven for 45 minutes or until tomatoes are browning nicely and the garlic is caramelized.
• Remove leaves from basil stalks and rinse in cold water. Spin out in a salad spinner or pat dry on paper towels. Measure out two cups of basil leaves and then chop.
• While tomatoes are roasting. Add last tablespoon of olive oil and butter to 6 quart soup pot or dutch oven, add chopped onion and saute over medium heat until soft.
• Remove roasting tomatoes from oven and add to pot with onions, making sure to get every bit of juice and all the yummy roasted bits.
• Add sugar, red pepper flakes, can of whole tomatoes and all the sauce, and chicken stock to the pot. Cook until starts to boil lower temperature and simmer for 15 minutes. If you have an immersion blender add basil and blend soup until a smooth consistency. Simmer for an additional 15 minutes.
• Regular Blender: If you do not have an immersion blender you can use a regular blender place half of the soup at a time in blender with basil and blend until smooth. CAUTION when blending hot liquid it can blow the top off the blender so keep a firm hand on the top of the blender while blending. Return to pot and cook another 15 minutes.