This is such a warm and comforting dish. It is also a dish that you can tailor to your own personal taste and with what you have in your pantry and refrigerator. You can add fried bacon, guanciale or Italian sausage for a meaty and hearty dish. For richness, you can add a Parmesan rind. Or go vegetarian and use vegetable or mushroom broth instead of chicken. You can also tear the country loaf into pieces and fry them in olive oil and garlic for rustic croutons. However you make this dish, you are going to love it!
Place the tomatoes in a medium bowl and poke small holes in them with a fork or paring knife. (This will prevent them from exploding and shooting seeds everywhere when you crush them.) Crush the tomatoes with your hands, a potato masher or a fork, and break them up into small pieces. Set aside.
Stir 1/4 cup plus 2 tablespoons oil and half of the garlic in a small bowl and let sit until ready to use.
Heat the remaining 3 tablespoons oil in a heavy-bottomed large pot over medium-high heat. Add the carrots, celery, onions, remaining garlic, oregano, red pepper flakes, bay leaves, 1 tablespoon plus 2 teaspoons salt and 1/2 teaspoon ground black pepper. Cook, stirring occasionally, until the vegetables are tender and just begin to brown, 8 to 10 minutes.
Add the reserved tomatoes and any accumulated juices and cook until the liquid evaporates, about 3 minutes. Add the chicken broth, cover and bring to a boil. Cook until the vegetables are just cooked through, about 5 minutes. Add the beans, kale and pasta and cook, stirring occasionally, until the pasta and kale are tender, about 9 minutes.
Meanwhile, make the garlic toast. Brush the top of each slice of bread with the reserved garlic oil, pushing the garlic into the crumb of the bread. Heat a large skillet over medium heat and melt 1 tablespoon butter. Add half of the bread, oiled-side up, and cook until deep golden brown, 2 to 3 minutes.
Flip and cook until golden brown, 2 to 3 minutes. (You want this side slightly less toasted so that the garlic doesn’t burn and taste bitter.) Transfer to a platter and repeat with the remaining 1 tablespoon butter and bread.
Stir the parsley into the soup and season with salt, if necessary. Divide among bowls and top with a drizzle of olive oil, some shaved Parmesan and cracked black pepper. Serve with the garlic toast.