Tomato Butter Sauce:
- 2 tablespoons olive oil, plus more for drizzling
- ½ teaspoon crushed red chili flakes
- 4 cloves garlic, minced
- 1 bay leaf
- 1 medium yellow onion, minced
- 1 sprig rosemary
- 6 tablespoons butter, cubed
- 2 cans whole peeled tomatoes, 28 ounces each, crushed by hand
- ½ cup pitted green Castelvetrano olives, halved
- ¼ cup finely grated Pecorino Romano
- 2 tablespoons fresh oregano, roughly chopped
- 1 large bunch Swiss chard, stems removed and chopped (about 6 cups)
- 5 tablespoons olive oil
- ¼ cup homemade bread crumbs
- 1 large onion, finely diced
- 3 tablespoons fresh parsley, roughly chopped
- 1 teaspoon rosemary, chopped
- 4 anchovy fillets in oil, chopped
- 4 cloves garlic, minced
- Pinch of red chili flakes
- 2 teaspoons lemon zest
- 1 pound of cleaned squid, bodies and tentacles separated
- 1 cup white wine
- Arugula and lemon for serving
To Make the Tomato Sauce:
Add the olive oil to a 5 QT Dutch oven and heat it over medium heat. Stir in the onion and sauté until translucent, about 4-5 minutes. Add the garlic, rosemary, bay leaf and chili flakes. Pour in the hand-crushed tomatoes and butter, and season it with salt and pepper. Bring the sauce to a simmer and then lower the heat. Cook uncovered until the sauce thickens and is reduced, about 30-40 minutes. Add the olives and oregano and season if necessary.
For the Calamari:
Toast the breadcrumbs in a small skillet over medium heat. Add one tablespoon of olive oil and breadcrumbs, cooking until they are browned. Pour them into a medium bowl.
In a large sauté pan, heat 1 tablespoon of oil over medium heat. Mix in the chard, season it with salt and pepper and sauté until it is wilted, about 5 minutes. Let the chard cool slightly, then squeeze out any excess liquid and add it to the bowl with the breadcrumbs.
Wipe out the sauté pan and add 2 tablespoons of olive oil. Heat it over medium heat and sauté the onions until they are soft, about 8 minutes. Mix in the parsley, rosemary, anchovies, garlic and chili flakes, cooking about 2 minutes more. Transfer the mixture to the bowl with the breadcrumbs. Stir in the lemon zest and season if necessary.
Rinse the calamari well and pat it dry. Fill each squid body with a few teaspoons of the chard mixture, securing the ends with a toothpick. Season both the stuffed bodies and the tentacles with salt and pepper.
Heat a large 12” skillet over medium-high heat. Pour in 1 tablespoon of olive oil and add the squid bodies. Cook, flipping once, about 4-5 minutes total. Add the tentacles around the bodies and pour in the wine. Turn the heat to high. Cook for about 2 more minutes while the wine boils and reduces.
Remove the toothpicks from the calamari. Spoon some of the warm tomato sauce on a large plate or platter. Place the calamari over the sauce and garnish with the arugula and lemon wedges. Drizzle the entire dish with more olive oil.