Making Italian stuffed olives is a ton of work but it brings my family together

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They’re called Olive all’Ascolana but in our family, they’re just “stuffed olives.”

Unfortunately, the words “stuffed olives” don’t come close to capturing the history, culinary effort and gastronomic pleasure that these little appetizers represent. These are not the “stuffed olives” that you find in jars with a sad sliver of red pimento sticking out of each end.

No, these are lovingly handmade fried balls of meat and olive with a history that dates back centuries. In our family, they have a cult-like status. Like many specialty ethnic dishes, they only make an appearance once or perhaps twice a year. For us, it’s Christmas. That’s it. And because of the ridiculous time and effort that goes into making them, we have deemed that not every guest is worthy of stuffed olives. You don’t get served the stuffed olives of Ascoli if you say, “I don’t really like olives.” Or if, in the past, you grabbed the first one and carelessly popped the whole thing into your mouth like a Malteser.

Every year in December I get together with my two sisters and two brothers to make them. We are following in the footsteps of our mother and her sisters, who would gather annually to make the stuffed olives and a few other seasonal dishes such as cheese pizza (which is not really pizza, but that’s another story) and anisette biscotti.

Our roots are Italian on both sides: my father, Ugo Benedetti, grew up in Conegliano, Treviso, and was a proud Trevisan. My mother, Mary Carpani, was born in Canada, but her parents, Agostino and Julia, hailed from the town of Ascoli Piceno, in the region of Le Marche, (The Marches in English) which made her Marchigian. Le Marche, one of Italy’s 20 regions, is not as famous as its neighbours Emilia-Romagna, Umbria and Tuscany, but it is a beautiful collection of five provinces nestled between the Apennine Mountains and the Adriatic Sea. Le Marche is famed for its picturesque medieval villages, including Ascoli, which boasts stunning Travertine piazzas and a history of great food. Growing up, our household cooking oscillated between my father’s favourite Venetian dishes, many of which featured butter, veal, cream and the king of cheeses, Parmigiano-Reggiano, and my mother’s Marchigiano meals, redolent with chicken livers, tomato, green olives and topped with the sheep milk cheese, Pecorino, or what we called Romano. We loved all our mother’s family’s food, but the hands-down favourite were the meat-stuffed olives of Ascoli.

Olive all’Ascolana, like dumplings or perogies, is a relatively simple dish that is time consuming, fussy and, for the most part, historically executed by groups of women. Like ravioli or gnocchi, once you decide to make stuffed olives, you may as well commit to making a lot of them, so my siblings and I set aside a full day. In a way, making the olives was a bit of an excuse for getting together. Our family gatherings at Easter and Good Friday and Christmas always revolved around food – veal cutlets alla Milanese, steaming tortellini soup, fried calamari, trays of cannelloni, the list goes on and on. But, as each of our families grew, it became harder and harder to all come together in one place for holiday dinners. Then, when our parents were both gone, we were faced with a dilemma. Our family hub – our parent’s house where we had grown up – was sold and for a while we stopped gathering for holiday meals. Then, one winter, my sister Rosanne suggested an alternative: Why don’t we all get together for a cooking day, specifically to make the famed stuffed olives? We all jumped at the chance.

One of the reasons you need a team of people and a whole day is because the first step in making stuffed olives is peeling the olives. That’s right. Each olive has to be hand peeled. If this sounds crazy, that’s because it is crazy. You need a sharp paring knife, steady hands and a lot of time. You cannot rush peeling an olive. There’s a certain knack to it and if you do it right you will delicately slice off most of the flesh of the olive in an unbroken spiral, like perfectly peeling an apple. When it works you get a ribbon of olive that you can wrap around the ball of meat stuffing. That’s the key to stuffed olives: you don’t actually stuff the olive; rather you gently encase the meat in the olive skin creating a perfect ball of deliciousness.

Making stuffed olives requires co-ordination and teamwork. It’s a production line. Rosanne and Paula roll the meat stuffing into perfect small balls. We briefly debate the size. I like them bigger; Rosanne prefers them smaller. “They’re not supposed to be golf balls, " says my brother, Robert.

“More like ping pong balls,” says Joe.

We carefully wrap each ball in olive and place them on the tray. Then we dip each ball in egg, roll it in flour, dip it again in egg and bread crumbs. Then we carefully drop the balls into hot oil. As they become golden brown, we scoop them out and deposit them on a paper-towel-lined tray. The assembly line goes on until all of the olives are fried. On most olive days, we work from 10 in the morning to past 6 p.m. By day’s end, we have peeled, stuffed, rolled and fried about 300 olives. Of course, as we work, we talk and talk and talk: updates about our kids, health woes and, while we leaf through a stack of old family photo albums, we exchange stories about our parents and relatives, our friends and our shared childhood. We also stop for a delicious lunch that includes wine and a lot of laughs.

At day’s end, we divide the olives by five and carefully pack them into plastic containers. Then, it’s hugs all around and we each head home, exhausted.

And so when I reheat the stuffed olives in the oven this Christmas and carefully take my first bite, I will think of the craft and the care that went into making them. I will think of the love and the laughter of my siblings as we worked all day together in the kitchen. I will think of our Carpani family roots in Ascoli Piceno and mostly I will think of my parents, especially my mother, standing in the kitchen with her apron and her hairnet, lovingly making her famous stuffed olives for Christmas.

Maybe that’s why they taste so good.

Paul Benedetti lives in Hamilton, Ont.