Red Wine-Braised Baby Octopus with Black Olives

• HEALTHY
• MAKE-AHEAD

Ingredients

1. 3 tablespoons extra-virgin olive oil
2. 1 large onion, cut into 1/2-inch dice
3. 1 large carrot, cut into 1/2-inch dice
4. 2 garlic cloves, minced
5. 2 celery ribs, cut into 1/2-inch dice
6. 1/4 teaspoon crushed red pepper
7. 1 bay leaf
8. One 14-ounce can chopped tomatoes
9. 2 pounds baby octopus—cleaned, heads halved, tentacles quartered
10. Salt and freshly ground pepper
11. 2 cups dry red wine, such as Syrah
12. 1 cup pitted kalamata olives, rinsed
13. 1/2 cup chopped parsley
14. 6 slices of sourdough bread, toasted

1. In a medium enameled, cast-iron casserole, heat 2 tablespoons of the oil. Add the onion, carrot, garlic, celery, crushed red pepper and bay leaf and cook over moderately high heat, stirring, until softened, about 8 minutes. Add the tomatoes and their juices and simmer for 2 minutes, until slightly reduced. Remove from the heat.
2. In a large skillet, heat 1 1/2 teaspoons of the oil until shimmering. Add half of the octopus, season with salt and pepper and cook over high heat, stirring, until starting to brown, about 2 minutes. Scrape the octopus into the casserole. Repeat with the remaining 1 1/2 teaspoons of oil and octopus. Add the red wine to the skillet and bring to a boil, scraping up the browned bits on the bottom. Pour the wine into the casserole.
3. Simmer the stew until the octopus is tender, 30 minutes. Add the olives and simmer for 5 minutes longer. Discard the bay leaf. Season the stew with salt and pepper and stir in the parsley. Set the toasts in bowls, top with the stew and serve.