There is something deeply twisted about stuffing an animal’s body with its own legs, then cooking it. But in this case, it’s also extremely delicious. Stuffed calamari are part of virtually every Italian island culture; the seasoning and components of the bread crumb mixture change slightly from place to place, but the concept is the same: the calamari bodies are stuffed, then cooked until perfectly tender. I have chosen the Bay of Naples and Pontine Islands as inspiration here, as their versions are quite similar. To make the recipe more Sicilian, use ¼ cup toasted pine nuts and 2 tablespoons currants or raisins, soaked in water to plump them up, instead of, or in addition to, the olives and capers.
Pro Tip: Use a food processor to chop the squid tentacles; pulse until the pieces have reached the desired size.
8 squid (about 3 pounds total), cleaned, bodies separated from tentacles
4 tablespoons extra-virgin olive oil
1 garlic clove, smashed and peeled
2 cups coarse plain bread crumbs or panko
2 large eggs, beaten
½ cup finely grated aged pecorino or Parmigiano- Reggiano cheese
¼ cup black olives (I like Gaeta), rinsed, pitted, and chopped
2 tablespoons salted capers, rinsed, soaked until their saltiness mellows, then drained and chopped
2 tablespoons finely chopped fresh flat-leaf parsley, plus more for garnish
½ cup dry white wine
2 cups cherry tomatoes, halved
Chop the squid tentacles into ¼-inch pieces. Heat 1 tablespoon of the olive oil in a pan over low heat. When the oil begins to shimmer, add the garlic and cook just until it takes color, about 3 minutes. Add the tentacles to the pan, increase the heat to high, and cook, stirring frequently, for 30 to 40 seconds. Remove from the heat. Discard the garlic.
Transfer the tentacles to a medium bowl. Add the bread crumbs, eggs, pecorino, olives, capers, and parsley and stir to combine. Season with salt. The mixture should be moist but not wet. If it seems dry, add a bit of water a tablespoon at a time until it reaches the consistency of wet sand.
Use a spoon to hold open the cavity. Fill each squid body with the bread crumb mixture, dividing it evenly and packing down lightly while taking care not to overstuff the bodies, as the squid will shrink as it cooks. Seal the bottom of the bodies shut with a toothpick.
Meanwhile, heat the remaining 3 tablespoons olive oil in the same pan over medium-high heat. When the oil begins to shimmer, add the stuffed squid and cook for 11/2 to 2 minutes per side, until they become opaque. Add the wine and cook until the alcohol aroma dissipates, about 1 minute. Add the tomatoes, season with salt, and cook, covered, until the squid is tender and cooked through, 20 to 25 minutes.
Plate the stuffed squid and spoon the tomatoes and sauce over the top. Serve sprinkled with fresh parsley.