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Restauranteur Michael Carlevale, right, and Richard Eppstadt in their new restaurant in Toronto, July 12, 1993.Fred Lum/The Globe and Mail

Charming, generous, daring, exacting, Michael Carlevale raised the level of Italian cooking in Toronto and created a series of ristoranti in the 1980s and '90s that set a new standard of sophistication – glamorous places to see and be seen.

The old family-style Italian dishes – lasagna, spaghetti, pizza dripping with tomato sauce – were out. Mr. Carlevale taught his clientele to prefer the simple, fresh cucina nuova, the new cooking, that was then rapidly conquering New York as well as the top restaurants of Italy. The high-water mark was his Prego della Piazza at the corner of Avenue Road and Bloor Street, with its flower arrangements and burnt-orange walls that evoked the feel of dining in Rome.

Prego opened in 1987 but before it took off like a rocket, Mr. Carlevale felt he had to teach Torontonians how to behave in a restaurant. Massimo Capra, then a 29-year-old chef who had come to Canada after training in the Parma area of Italy, witnessed this lesson in the course of a job interview at Prego with Mr. Carlevale. "We were talking, having an espresso on a weekday morning, getting to know each other," he recalls. "About quarter to 12, a large party came in, about 20 people, who probably worked at the same office."

They were served some aperitifs, and given time to study the menu. "Then Michael got up and went to take their order," he recalls. One wanted a salad but without the croutons, another asked for extra cheese on her order, a third wanted a substitution for the mushrooms. Everyone seemed to know better than the trained cooks in the kitchen what should be put in or taken out of a dish.

"Michael put down his pencil and said, 'Ladies, the drinks are on me, but you are going to have to find your lunch elsewhere.'" Mr. Capra was bowled over, since the restaurant was empty: "Such conviction in his beliefs! It was beautiful – I was impressed. A restaurant is not a free-for-all. I said, 'I want to work with you.'"

Mr. Carlevale then showed the young chef around his newly acquired restaurant. While most restaurants want to cram in as many tables as possible, he pointed out tables he wanted to remove. "Some were uncomfortable, or he wanted to facilitate the movement of the servers or he needed a place for flowers. That was a spectacular way of thinking," adds Mr. Capra, who worked 16-hour days as Mr. Carlevale's chef for 10 years until he left to open his own restaurant, Mistura.

Prego proved a magnet for movie stars, producers, publishers and others in the entertainment business, with its patio providing a stylish party venue during the Toronto International Film Festival. Pierre Trudeau ate there, as did Demi Moore, Cher, Catherine Deneuve, Jack Lemmon, John Malkovich, Harper's editor Lewis Lapham and film producer Robert Lantos, among other celebrities, before the festival moved away from Yorkville.

"You could barely get a table if you were not suitably Yorkvillian," observes Joanne Kates, who was The Globe and Mail's restaurant critic from 1974 to 2012.

Mr. Carlevale died in his sleep on Dec. 27 at his home in Osterville on Cape Cod, where he lived with his father. Autopsy results are pending, but the likely cause was a heart attack.

Michael Edward Carlevale was born in Boston on April 13, 1949, the eldest of five children of Edward Carlevale, a high-school teacher, and Lois Carlevale (née MacDonald), a housewife with roots in Cape Breton, N.S.

A good student with an ear for languages, the teenage Michael attended the famous Boston Latin School, the oldest high school in the United States, where admission is by examination and the curriculum includes a heavy dose of Latin. He was close to his Italian-born grandmother, who taught him to cook and to speak Italian. Later, he became fluent in French and was passable in Greek.

He took a BA in classics at Queen's University, in Kingston, where he met Catherine Harris, who became his best friend. According to Ms. Harris, he came to Toronto and worked in construction for about three years, then studied public health at the University of Toronto while supporting himself by cooking privately for a family. That led to work in a series of restaurants, which he found suited him.

"Michael and I worked at Crispins around 1979, [at] Church and Gerrard," recalls restaurateur Joey Bersani, who is also Italo-American. "Michael had an idea for a restaurant to be called Carlevale's on Avenue Road."

"Carlevale's opened with a loan from Michael's father and my father," Ms. Harris recalls. Mr. Carlevale, senior, came from Boston, she says, to do some carpentry to get the small split-level space north of Davenport in shape to open.

With Michael Carlevale in the kitchen, the intriguing new Italian restaurant was filled every night and Mr. Bersani, who had gone back to his native New York for a time, returned to Toronto to help his friend. Just south of Carlevale's, the two opened Bersani and Carlevale's in 1980, and it was a beloved lunch and dinner spot for residents of the Annex and Rosedale for the next 13 years.

"We were two guys in our 30s," recalls Mr. Bersani, whose current restaurant, Cantine, is at the former location of Bersani and Carlevale's. "We featured fresh-made pasta and when we moved here we had catering and take-out Italian food (at the front of the restaurant), sort of like what Pusateri's does today, and we served cappuccino and espresso. That was our time. There was no Starbucks, no Second Cup then."

Following his partnership with Mr. Bersani, Mr. Carlevale ran the food service at the YMCA, did some consulting work, then started Prego. Well-educated, he could talk to anyone and was a warm and flamboyant host – all part of the alchemy of the restaurant business. "We had all the big actors, big producers, writers, musicians," Mr. Capra recalls. "They came into the kitchen to say hello. Michael said, 'This is theatre, and all in my house.'"

According to Ms. Kates, Mr. Carlevale "was a food leader and a great chef at Carlevale's and Bersani and Carlevale's. His Italian cooking had more verve and flavour than most of the rest of the Italian cooks in town, put together. After that, everything he did amounted to creating buzz."

With his friend Franco Prevedello, who owned Centro, he made regular trips to California and to the annual Verona Wine Fair, acquiring an outstanding wine list for Prego while also noting the latest food trends.

"Michael had a strong knowledge of the kitchen, and he was a great host and he was always ready to try something new," Mr. Prevedello recalls. "He was fabulous to travel with, a very intelligent and learned man. We had many conversations about food and wine."

In 1982, Mr. Carlevale and Mr. Capra opened the wine bar Enoteca (cost: $1.5-million) next to Prego, with frescoes copied from a book on Tuscan architecture and banners from the Palio, Siena's traditional horse race. "We had lots of Riedel crystal glasses, a different shape for every wine, and served small plates, tapas-style," Mr. Capra recalls.

Meanwhile, a fruitless search for really good baklava in Toronto gave Mr. Carlevale the idea of opening Byzantium, a beautiful Greek-Mediterranean restaurant on Church Street, serving feta salads, baba ghanoush, koftas, a proper hummus and the incomparable Greek sweets of pastry chef Renée Foote.

Mr. Capra recalls that Mr. Carlevale took a box of Ms. Foote's baklava to a Greek bakery and put it on the counter, just to demonstrate how it should taste. "He said in his Boston accent, 'Throw yo-s in the gaw-bich.'" Byzantium proved unsuccessful, however, and had to be sold.

In 1995, they opened the lavish steakhouse Black and Blue. "I cooked steak and lobster; the steaks were dry cured and properly aged," Mr. Capra recalls. "The place was full every single night. We had specialty dinners for chefs from Italy and France and for the embassies. Michael made connections with people." But with costs running to about $3-million a year, Black and Blue closed after five years.

"Like too many great cooks, Michael turned from what he excelled at – cooking – and did not quite succeed at sustaining large, trendy restaurants," Ms. Kates says.

His most ambitious restaurant in Toronto was the Boston Club on Front St., opposite the Hummingbird Centre (now the Sony Centre for the Performing Arts), a fish and seafood restaurant that he opened in 1998 in homage to his birthplace, at a cost of about $3-million. A bar scene in the film American Psycho was shot there. It had pewter plates, custom chairs, wine buckets on elegant pedestals and a chef hired from Boston, who toured Toronto's fishmongers and pronounced what they sold disgusting. Fresh fish and seafood were thus flown in weekly from Boston at an astronomical cost.

"He tried to do too much and the place went belly-up relatively fast," Mr. Capra says.

Mr. Carlevale eventually declared bankruptcy on Jan. 31, 2008. "He was off the wall but he loved the restaurant business. 'You have to show them how it's done,' he'd say."

Ms. Harris knew another side of her long-time friend. "Michael was a deeply religious man, who went to church regularly," she says. "At Easter he hosted a Seder, using a text adapted for Christians."

Mr. Carlevale, who was gay, never married and maintained close ties with his family. He visited them often in Boston and was extremely generous to them. In 1991, he bought his parents a house on Cape Cod and, in 2010, moved there to live with them. His mother, Lois, died last year. His last venture was a restaurant in Hyannis, on the Cape, that did not work out.

He leaves his father, Edward Carlevale; sisters Jean, Janet and Jennifer; and brother, Edmund.

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