Preheat oven to 400°F.
Place drained diced tomatoes on a baking sheet. Drizzle with 1 tablespoon of olive oil. Season with salt and pepper, to taste.
Place in preheated oven and roast for about 40 minutes (Watch them and stir around if they start to burn). Remove from oven and set aside.
In a large stock pot, heat 1 tablespoon olive oil and butter over medium high heat.
Add garlic. Cook for 30 seconds.
Add onion, celery and carrots. Sauté until vegetables are softened and onions are translucent.
Add roasted tomatoes, reserved tomato juice, chicken stock and sugar. Simmer until soup starts to thicken, about 15 minutes.
Add the half and half, basil and oregano. Mix well.
Taste. Add salt and pepper, to taste. Mix well.
Pour soup into a food processor fitted with a steel blade. Purée for 2 - 3 minutes or until the soup is smooth.
Return soup to the stove top and bring to a simmer.
Taste. Add salt and pepper, or any other seasoning, to taste, if necessary. Mix well. Serve hot with croutons and fresh basil.