Adapted from original recipe by Michael Chiarello
For the soup:
12 large (about 4 pounds) tomatoes, stemmed and quartered
1/2 cup extra-virgin olive oil, divided
1/4 cup good-quality balsamic vinegar
12 large garlic cloves, peeled
1/2 teaspoon freshly ground black pepper
1 cup chopped yellow onions
2 cups lightly packed fresh basil leaves, plus few leaves torn for garnish
2 cups cold water
For the Matzah Toasts:
5 pieces square matzah
Extra-virgin olive oil
Preheat the oven to 500 degrees.
Prepare the tomatoes. In a large bowl, mix the tomatoes, 1/4 cup of the oil, the vinegar, garlic, salt, and pepper to taste. Spread the tomatoes out on a non-reactive baking sheet. Roast the tomatoes in the oven until very dark in spots, 35 to 40 minutes. Remove and allow to cool a bit.
Prepare the matzah toasts: Lightly brush the matzah on both sides with oil and season with salt. Place the slices on a baking sheet and toast in the oven until the matzahs are golden brown and just beginning to crisp, about 4 minutes.
In a large saucepan over medium heat, combine remaining 1/4 cup oil, the onions, and a pinch of salt. Cook until the onions are very soft, 8 to 10 minutes, stirring occasionally. Add the 2 cups basil leaves and saute with the onions for about 1 minute.
Add the roasted tomatoes and water to the saucepan. Bring the mixture to a simmer and cook for 10 minutes. Season with salt and pepper, to taste. Purée the tomato mixture in an immersion blender right in the pot. The mixture should be very smooth. You should have about 8 cups. You can prepare the soup to this point and refrigerate it. When ready to serve, pour the soup into a medium saucepan and bring it to a slow simmer over medium heat or serve at room temperature. Add the matzah toasts to the top.
Garnish with torn basil leaves.