Start by thoroughly cleaning the squid under cold running water; ensure it's free of any grit or debris. Drain well and then finely chop the tentacles and fins using a sharp knife, setting them aside for the filling.

In a skillet over medium heat, add 2 tablespoons of olive oil and sauté the chopped squid parts along with one minced garlic clove until the moisture evaporates—about 5 minutes. Transfer the mixture to a food processor, combining it with breadcrumbs, grated Pecorino Romano cheese, chopped parsley, capers, salt, and pepper. Pulse until crumbly, then taste and adjust seasoning as desired.

Using a small spoon, gently fill each squid tube with the prepared filling, taking care not to overstuff them. Once filled, secure the open ends with toothpicks, and prick the squid lightly with a fork to prevent bursting during cooking.

In the same skillet, heat an additional 3 tablespoons of extra virgin olive oil over medium heat. Sauté another minced garlic clove until fragrant, about 1-2 minutes. Deglaze the pan with ¼ cup of dry white wine, allowing it to simmer and reduce for 2-3 minutes before adding the canned tomatoes, olives, capers, parsley, salt, and pepper. Stir well and let it simmer briefly, about 5 minutes.

Gently place the stuffed squid into the simmering sauce, ensuring they are covered. Reduce the heat to low, cover the skillet, and let the squid simmer for 30-60 minutes, or until tender.

Once the squid is cooked, carefully remove it from the sauce and slice as desired. Arrange the slices on a warm platter and spoon the rich tomato sauce over the top. For a complete meal, consider tossing cooked pasta in the sauce.