Prep. Preheat oven to 400 F and line a baking sheet with parchment paper.
Tomatoes. Toss quartered tomatoes (3 lbs) in olive oil (1/4 cup), salt (1 tablespoon), and pepper (1 1/2 teaspoon) and spread onto a baking sheet. Bake for 45 minutes, or until the edges start to brown (will vary depending on how small your slices are).
Crisp + Saute. Meanwhile, cook bacon (8 pieces) in a large 8-quart stockpot until crisp. Set cooked bacon aside on a paper towel-lined plate. Remove all but 2 tablespoons of bacon grease from the stockpot. Add chopped onion (1 cup) and saute until soft, about 8 minutes. Add minced garlic (1 tablespoon), and cook until fragrant, about 2 minutes.
Simmer. Stir in the roasted tomatoes and any juices from the pan, along with the fresh basil (4 cups), thyme (1 teaspoon), crushed red pepper flakes (1/4 teaspoon), and chicken stock (1 quart). Bring soup to a boil, then reduce to a simmer and cook uncovered for 40 minutes.
Blend. Ladle soup into a blender, along with the bacon and heavy cream. Blend until the soup is smooth.
Serve. Top with fresh basil, and additional crumbled bacon. Enjoy!