Preheat oven to 400°F. Arrange carrots, tomatoes, onion, squash and garlic on sheet (I use parchment on my baking sheet). Drizzle with oil, if using. (I didn't use oil, just a bit of veggie broth). Sprinkle with salt and pepper. Toss to coat. Bake until vegetables are brown and tender, stirring occasionally, about 45 minutes.

Transfer carrots and squash to work surface. Cut into 1/2-inch pieces; set aside. Peel garlic cloves; place in processor. Add tomatoes and onion; puree until almost smooth. Pour 1/2 cup broth onto baking sheet; scrape up any browned bits. Transfer broth and vegetable puree to large pot. Add 5 1/2 cups broth, kale, thyme and bay leaf to pot; bring to boil. Reduce heat; simmer uncovered until kale is tender, about 30 minutes.

Add beans and reserved carrots and squash to soup. Simmer 8 minutes to blend flavors, adding more broth to thin soup if necessary. Season with salt and pepper, any additional spices to kick up the flavor, and a splash of red wine vinegar (totally optional). Discard thyme sprigs and bay leaf. (Can be made 1 day ahead. Cover and chill. Bring to simmer before serving.)