Pour the tomatoes and juice into a large bowl. Crush the tomatoes with your hands and set aside.
Pour the olive oil into a large soup pot or Dutch oven set over medium-high heat until shimmering. Add the onion, carrots, ½ teaspoon salt and ½ teaspoon pepper. Cook, stirring frequently, until the onion is soft, about 5 minutes.
Reduce the heat to medium. Add the garlic, red pepper flakes and tomato paste. Cook, stirring constantly until the mixture darkens and starts to stick to the bottom of the pan, 3 to 4 minutes. Sprinkle the flour over the vegetables. Cook, stirring constantly for about 2 minutes, scraping up the browned fond on the bottom of the pot.
Pour the crushed tomatoes into the pot. Add the bay leaf, basil, chicken broth and brown sugar. Simmer uncovered for 30 minutes, stirring occasionally.
While the soup is simmering, prepare the tortellini according to package directions. Drain and toss with a teaspoon or two of olive oil. DO NOT overcook the tortellni pasta.
REMOVE the bay leaf and discard. Carefully move the soup pot from the stovetop. Using a stick or immersion blender, process the soup until smooth. Season with salt and pepper, to taste. Add the cream (if using) and blend until incorporated. Return the soup to the stovetop and cook on low for 10 minutes, or until heated through.
Serve each bowl of soup topped with 4 or 5 tortellini, a drizzle of pesto, Parmesan cheese and black pepper, as desired.
Alternately, add the tortellini to the soup pot and stir to incorporate.