With calamari you either need to cook it quick or let it stew. There is no in-between. Once added to the hot pot, it will cook almost immediately, but within a few minutes will become rubbery. By stewing them in the tomatoes, they will become tender once again. The wonderful thing is, once you’ve stewed them, you can cool the sauce and reheat it later on.
1/3 cup extra-virgin olive oil
2 medium yellow onions, thinly sliced into half moons
8 cloves garlic, thinly sliced
1 teaspoon red pepper flakes, plus more for serving, optional
1/2 cup dry red wine
One (90-ounce can) San Marzano whole peeled tomatoes, crushed by hand
2 pounds calamari, cleaned, tubes sliced into 1/2-inch rounds, tentacles halved
1/4 teaspoon freshly ground black pepper
2 pounds linguine, cooked to al dente
Salt, to taste
Parsley, for serving
1.Combine the oil and onions in a large Dutch oven.
2.Cook, stirring often, until the onions are softened but have not taken on any color, about 10-12 minutes.
3.Add the garlic and red pepper flakes and cook for 2 additional minutes.
4.Add the wine and cook until it is almost fully evaporated, about 2 minutes more.
5.Add the tomatoes, calamari and pepper and bring to a simmer.
6.Cook, stirring often, until the calamari is tender, about 1 hour.
7.Season with salt, to taste.
8.Serve with linguine and garnish with chopped parsley.