2 pounds assorted heirloom tomatoes, cut into wedges
1 pound assorted small tomatoes, larger tomatoes cut in half
2 tablespoons minced fresh chiles, such as jalapeño
Bring a small saucepan of water to a boil. Prepare a bowl of ice water.
Add the green tomato to the boiling water and cook until slightly softened and the skin is pale, about 7 minutes. Drain and transfer to the bowl of ice water and cool thoroughly, then drain again. Peel and core the green tomato and cut it into large chunks.
In a blender, combine the green tomato chunks with the vinegar and sugar and puree until the tomato is finely chopped. With the machine on, add the oil in a slow stream and blend until smooth. Season with salt and pepper.
Arrange all of the tomatoes on a large platter. Sprinkle with the chiles and season with salt and pepper. Drizzle the dressing all over the salad and serve.
The green tomato vinaigrette can be refrigerated for up to 3 days before serving.