Red Wine-Braised Baby Octopus with Black Olives

 ACTIVE:  40 MIN 
 TOTAL TIME:  1 HR 30 MIN 
 SERVINGS:  6

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

 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. 
 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. 
 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.