For the calamari:
- 11 clean medium calamari tubes, about 5 to 6 inches long
- 1/2 pound peeled, deveined medium shrimp, roughly chopped
- 3 cloves garlic, smashed and coarsely chopped
- 2 cups coarsely chopped baby spinach
- 2 eggs
- 1/2 to 3/4 cup bread crumbs
- 1/2 cup grated Parmigiano-Reggiano
- 1/2 bunch fresh oregano, leaves chopped
- 2 pinches crushed red pepper flakes
- Kosher salt
For the sauce:
- Extra-virgin olive oil
- 1 large or 2 small onions, finely diced
- Pinch crushed red pepper flakes
- Kosher salt
- 2 cloves garlic, smashed and finely chopped
- 3/4 cup dry white wine
- 1 (28-ounce) can Italian plum tomatoes
To make the calamari:
Roughly chop 3 of the calamari tubes and add to a food processor with the coarsely chopped shrimp and garlic. Pulse into a coarse paste. Remove to a large bowl and add the spinach, eggs, bread crumbs, cheese, herbs, and pinch of crushed red pepper. Season with salt and stir to combine. The mixture should be a little chunky but moist and holding together. Test the seasoning of the mix by making a mini patty, cooking it in a small pan and eating it. It should taste really good! If it doesn't it is probably missing salt. Add more salt, to taste. Divide the stuffing among the 8 remaining calamari bodies and secure closed with toothpicks.
To make the sauce:
Coat a large, wide skillet or saucepan with olive oil and add the onions and a pinch of crushed red pepper. Season with salt and put the saucepan over medium heat. Saute the onions until they are soft and aromatic, about 7 to 8 minutes. Add the garlic and cook another 2 minutes until fragrant. Stir in the wine and cook until the wine has reduced by half. Pass the tomatoes through a food mill or puree them in a food processor and add them and 1 cup of water to the pan. Season with salt, to taste, and simmer the sauce for 15 minutes.
Add the calamari to the pan and cook for 20 to 25 minutes turning them over halfway through the cooking time. Remove the calamari from the pan and remove the toothpicks. Reduce the sauce to thicken, if needed. Arrange the calamari on a serving platter and cover with the sauce before serving.