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Paul Phelan was born into the family that owned the Cara food empire: Swiss Chalet, Harvey’s, airline catering and more.Fred Lum/The Globe and Mail

Paul David Phelan was a businessman, sailor, athlete, early personal computer user, devoted family man and bon vivant – although not necessarily in that order, as his huge successes in business were certainly matched by his passions for sailing, other sports and family.

He was born into the family that owned the Cara food empire: Swiss Chalet, Harvey’s, airline catering and more. He had a falling out with his sisters and eventually was bought out of the family company but was happy to be on his own and did incredibly well from owning fast-food franchises, including a percentage of Second Cup, and starting Chartright, the second-largest private jet business in Canada.

On top of it all, Mr. Phelan was an astute investor. He used his computer in the 1970s to work out algorithms to trade in commodities and currencies. He had a Bloomberg terminal at home to watch markets.

“One of his great successes was in the cannabis space,” said Fred Farncomb, his stockbroker who knew him when they were both students at Upper Canada College in Toronto. “He recognized it early and exited judiciously. It was perfect timing. He made a ton of dough.”

Mr. Phelan was born in Toronto in 1951. He was often known just by his initials, P.D. His father, Paul James, was known as P.J., and his son Paul’s nickname is P.W.

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Mr. Phelan, centre, also owned a major interest in Aegis, which until the end of April owned the Second Cup coffee chain. It now owns another coffee firm and other interests.Ingrid Johansson Miz Monday Films (aka Miz Monday)/Handout

His mother was Helen Gardiner, whose father, Percy Gardiner, was a successful stockbroker. The Gardiner Museum in Toronto is named after them.

The Gardiner family was also in the food business; they owned Scott’s Hospitality, which brought Kentucky Fried Chicken to Canada.

Mr. Phelan had fast food on both sides of his family.

Mr. Phelan went to Upper Canada College, which was just a short walk from the family’s house on Old Forest Hill Road. At the private school, he was a star athlete playing football, hockey and cricket, according to Mr. Farncomb. As a teenager, he was fascinated by the stock market and would go downtown to visit the Toronto Stock Exchange gallery as well as the trading room of his grandfather’s brokerage firm. After UCC, he went to Huron College at the University of Western Ontario in London, Ont., where he studied English and film.

Mr. Phelan’s great-grandfather, Thomas Phelan, co-founded Cara in 1883. The company began as the Canadian Railway News Co., which ran newsstands in railway stations and diversified over the years into restaurants, catering and airport and in-flight food services. It also expanded into chains such as Swiss Chalet and Harvey’s. Mr. Phelan went into the family business. “He famously started as a line cook, and it was an extremely brief stint before he moved up in the company,” his daughter Jamie Phelan says.

“He played a pivotal role in the business, especially with Harvey’s and Swiss Chalet. There was a concept called twinning to put the stores together, and that was his idea,” another daughter, Jennen Phelan, says.

Mr. Phelan was a senior executive at Cara before his father P.J.’s illness in the 1990s brought about a family crisis and a contest for control of the company. In 1998, two of P.J.’s daughters and a niece took over, acquiring shares in a family holding company from Mr. Phelan.

Mr. Phelan later bought back into the company on the open market, but Cara was taken private in 2004.

Mr. Phelan did not sit still or live on the money he made from the Cara buyout. He was a creative entrepreneur. One of his smaller investments was a combined Swiss Chalet/Harvey’s franchise in Collingwood, Ont.

Perhaps his largest enterprise was Chartright Air Group, which owns and manages private planes, ranging from a Challenger 5000 Global Express GRS, Bombardier’s largest plane capable of flying across the Atlantic, to a twin-engine propeller-driven King Air plane.

Mr. Phelan also owned a major interest in Aegis, which until the end of April owned the Second Cup coffee chain. It now owns another coffee firm and other interests.

But his biggest love by far was sailing, which he was taught by his father. He raced at a competitive level in a Finn, a 15-foot Olympic class sailboat.

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Mr. Phelan's Open 60 sailboat, O Canada, on the open seas during the Transpacific Sailboat Race from Long Beach to Hawaii.Ingrid Johansson Miz Monday Films (aka Miz Monday)

“Paul was a gifted sailor,” says John Curtis, who runs Wind Athletes Canada, which was Mr. Phelan’s idea. “He wanted people to learn the joy of sailing.”

Mr. Phelan sponsored a 60-foot sailboat built to sail by one person, non-stop in an around-the-world race, the Vendée Globe. It is so difficult that more people have been to space than have successfully completed the race.

“Paul was a bit of a Zen master. He was not a perfect person, but he could teach people things,” Mr. Curtis says. “He did not look at things with a dollar figure. You could say that was because he was rich, but it was more than that. He wanted to think things through before someone could say you can’t do that.”

One example was a special instrument that could track where in the ocean the yacht was. It worked when conventional trackers failed. His 60-foot sailboat foundered in the Pacific and didn’t finish the race, but Mr. Phelan had the boat refitted in New Zealand and renamed it O Canada.

Mr. Phelan also sponsored four films about the international single-handed race. They are very dramatic. “These boats can go 30 knots when the average sailboat does six knots,” Mr. Curtis says.

In addition to sailing, Mr. Phelan was an early fan of windsurfing. He competed as far afield as Hawaii and organized windsurfing events in Collingwood. “He spearheaded windsurfing as a sport and later on in life funded windsurfing for the Olympics, particularly for women,” says daughter Jennen, who is a windsurfer herself. Windsurfing was first an Olympic sport for men in 1984 and for women in 1988.

Along with sailing and other charities, Mr. Phelan donated a lot of money to Upper Canada College and to Bishop Strachan School, where his mother attended. He was major donor to UCC’s arena. “My father joked that his father didn’t always came to watch his games, but now he can watch them for eternity,” his son Paul says. “He also funded a scholarship for students to attend Upper Canada who could not afford to go there. Those students came from all over the world and we would get a report every year and he was proud of how well they did.”

Some of his other major donations included funding the National Ski Academy in Collingwood and giving to the Sterling Hall School in Toronto.

Mr. Phelan had a playful side. On Canada Day he liked to strap dozens of fireworks to a chair, douse it with gasoline, then stand back and toss a Roman candle at it and watch the show. He would do this at his country place in Collingwood, but even did it a few times in his backyard in Toronto. “It was known in the family as the burning chair. I don’t know what our neighbours thought,” another daughter, Hayley, says.

Mr. Phelan had been working on a book for years. Its idea was that mankind migrated around the world by sailing rather than trekking overland. It was called The Water’s Edge, but it was never published commercially.

Paul David Phelan was born in Toronto on April 9, 1951. He died in Toronto on May 20, 2021. Predeceased by his daughter Paula, Mr. Phelan leaves his former wife, Rundi Phelan, and their children, Jennen, Jamie, Hayley and Paul, as well as four grandchildren and his two sisters.

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