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For some reason, I really don’t know why, I’ve always been afraid to cook calamari. As I was growing up, it was always one of my favorite meals on a Friday, when meatless meals were still mandatory for Catholics. More often than not, my aunt would prepare them stewed in a simple marinara sauce. They were either whole, stuffed with softened white bread that she combined with the chopped tentacles, eggs, and parsley, or cut up into rings. The stuffed version were usually served with pasta; the rings, with friselle, which might best be described as thick, rectangular, twice-baked bread biscuits, which were used to sop up the sauce. Once in a while, my aunt would also serve them cut into rings, lightly battered, and deep-fried, accompanied only by lemon wedges—but never with tomato sauce.

Wanting to recreate these dishes at home, I eventually confronted my fear of cooking these delectable creatures and started to deep fry calamari with, I might add, considerable success. Cooking them in sauce, however, continued to remain a challenge—until last Friday. That morning, I had intended to buy some Manila clams, which I intended to cook with Sardinian fregola. But when I got to the fish market, I spotted some beautiful calamari, glistening a lustrous white interlaced with light purple from the tentacles. I decided that it was time to take the plunge and stew them in tomato sauce.

Although I was confident about the sauce, I wasn’t quite sure how long I needed to cook the calamari. Almost every source I consulted warned against overcooking them, which would make them rubbery. Indeed, I knew this from my experience with frying. In fact, the majority of recipes I read suggested preparing the sauce separately and then adding the squid and cooking them for two minutes. Somehow, I wasn’t comfortable with this method, as I really wanted my sauce to be deeply flavored with the calamari and vice versa. I was certain that my aunt simmered her calamari slowly, but I wasn’t sure for how long.

Finally, I turned to one of my go-to books on Neapolitan cooking, Naples at Tableby Arthur Schwartz. It was here that I found a recipe that resembled closely my aunt’s preparation. It called for preparing a classic marinara and adding the calamari to the sauce after the first five minutes of cooking. The fish and the sauce are then gently simmered uncovered for about 30 minutes or until the sauce has thickened and the calamari are tender.

This was the recipe I used, and with some only minor variations (adding some salt and increasing the amount of tomatoes), I came very close to replicating my aunt’s stewed calamari. I served them over pasta. Next time, however, I’ll stuff them.

Calamari In Cassuola (Squid Stewed with Tomatoes) adapted from Naples at Table by Arthur Schwartz

The ingredients

The ingredients

3 tablespoons extra-virgin olive oil
2 large cloves garlic, lightly smashed
¼ teaspoon or more hot red pepper flakes
1 28-ounce can imported whole peeled tomatoes, preferably San Marzano, with their juices
¼ teaspoon dried oregano
Salt to taste
1½ fresh, cleaned calamari cut into ¼-inch rings, tentacles cut in half
¼ cup finely cut flat-leaf parsley

The cut calamari

The cut calamari

1. In a 2½ – to 3-quart saucepan or stovetop casserole, over low heat, combine the olive oil, the garlic, and the hot pepper. Cook until the garlic is soft and beginning to color on all sides, pressing the garlic into the oil a few times to release its flavor. Remove the garlic.

The cooked garlic

The cooked garlic

2. Add the tomatoes, the oregano, and the salt to taste and, with a wooden spoon, break up and coarsely crush the tomatoes. Increase the heat to medium high and simmer briskly, uncovered, for 5 minutes.

The sauce after 5 minutes

The sauce after 5 minutes

3. Reduce the heat to low, stir the calamari into the sauce and continue to simmer steadily, uncovered for about 30 minutes, or until the sauce has thickened and the calamari are tender. Some calamari may take longer to cook, in which case you may need to add a tablespoon or as many as a few tablespoons of water so the sauce doesn’t become too reduced.

The cooked calamari

The cooked calamari

4. Add the parsley and cook for another 15 seconds.

Cooked calamari with the parsley

Cooked calamari with the parsley

Note: I added the parsley after transferring the calamari to a skillet for tossing with the pasta.

5. Serve very hot, as is, with bread, or over freselle, or, as I did, tossed with pasta.

Wine Pairing: Lacryma Christi del Vesuvio Rosso

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