Preheat oven to 375°
In a large, high sided baking dish, combine tomatoes, ¼ cup olive oil, garlic, ½ cup basil leaves, 1 teaspoon salt & ½ teaspoon pepper. Toss to combine. Roast for 60 minutes, or until tomatoes are soft & wilted. Once cooked, remove basil & garlic & set aside.
In a large heavy bottom pot or Dutch Oven set to medium heat, sauté onion in remaining olive oil with ½ teaspoon salt & ¼ teaspoon pepper, until soft, but not browned, about 7-10 minutes.
Once onions have cooked, turn the heat to medium high & add 6-8 cloves from roasted garlic, thyme, oregano, red pepper flakes & anchovy paste. Cook for 1 minute, until herbs have toasted & anchovy paste has fully disappeared into the onions. Next, add wine & using a wooden spoon, scrape up any browned bits from the bottom of the pan. Cook until wine has reduced by half.
Add cooked tomatoes, remaining basil leaves, tomato puree & broth to the pot. Stir to combine.
Bring the soup to a boil, then reduce the heat to a low simmer. Simmer for 5 minutes.
To blend the soup in a blender: pour half of the soup into a high powered blender & blend until smooth. Repeat with remaining half, then return soup to the pot.
To blend the soup with a hand blender: place hand blender directly into the pot & carefully blend until smooth.
Taste the soup & if needed, add more salt. If the soup needs more broth, add extra both 1 tablespoon at a time until you reached your desired consistency.
Serve, drizzled with olive oil.
