Calamari Stewed with Tomatoes

Squid can be cooked one of two ways: For the blink of an eye, or for a long, long time. Anything in between and it is rubbery. This dish, which is our version of a Southern Italian classic called calamari in umido, takes the long view of calamari cooking.

Think of this dish as something between a stew and a pasta sauce. It’s every bit as good as-is—with crusty bread, of course—as it is accompanying pasta (go with a short pasta like penne, bowties or fusilli) or, even better, a creamy polenta. You can even add a little cheese to the polenta, if no one’s looking. Italians rarely mix seafood and cheese.

  • Prep: 15 minutes
  • Cook: 1 hour, 20 minutes
  • Yield: Serves 4-6.

You can buy frozen, cleaned squid in the freezer section of many grocery stores. Defrost by placing in refrigerator overnight, or in a bowl of ice water. This recipe does call for an anise-flavored liquor, which you can leave out if you want, but the dish will be better with it in.

Ingredients

  • 2 pounds cleaned calamari (squid), tubes sliced into rings and tentacles roughly chopped
  • 4 Tbsp olive oil
  • 1 sliced onion
  • 1 fennel bulb, chopped
  • 3 garlic cloves, chopped
  • 2 Tbsp tomato paste
  • 1/4 cup Sambuca or other anise-flavored liquor
  • 1 cup red wine
  • 1 28-ounce can of crushed tomatoes
  • Salt and pepper
  • 1/2 cup parsley, chopped
  • 1/4 cup fennel fronds, chopped

Method

1 Heat the olive oil in a large pot over medium-high heat. When the oil is hot, add the onions and fennel. Stir to coat with oil and sauté, stirring occasionally, until it begins to color, about 5-6 minutes. Sprinkle some salt over it. Add the garlic cloves and tomato paste and stir well to combine. Cook this for another 2-3 minutes, stirring once or twice.

2 Add the red wine, stir well, and increase the heat to high. Boil until the liquid is reduced by half.

3 Add the Sambuca or other anise-flavored liquor, and the crushed tomatoes. Stir in the calamari and bring the pot to a gentle simmer. Simmer for at least 1 hour. After an hour, taste a piece of calamari; It should be tender. If it’s not, keep simmering. Check for tenderness every 15 minutes afterward.

4 Once the calamari is tender, taste the stew for salt and pepper, adding if needed. Add the chopped parsley and fennel fronds. Stir well to combine and serve.

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