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Jack Singer just outside of Puerto Vallarta in 1973. (Grant Gallelli)
Jack Singer just outside of Puerto Vallarta in 1973. (Grant Gallelli)

BUSINESSMAN AND PHILANTHROPIST, 95

Calgary tycoon Jack Singer was larger than life Add to ...

Mr. Singer’s friend was actually the one smitten by the beautiful young lady, but her parents did not approve of the match. Mr. Singer showed up to convince them that he was her more “acceptable” kind of date, and then planned to hand her off to his buddy.

“But it didn’t end up that way,” Stephen said.

As Mr. Singer recalled in his biography, “I rang the bell at Shirley’s house. I was wearing a powder blue suit and I looked like a gangster. It was love at first sight.”

They quickly became a power couple of Calgary – fashionable, jet-setting party hosts.

They would remain together until Shirley died in 2001, producing two sons, Stephen and Alan.

By the 1950s and 1960s, Mr. Singer and his older brother, Hymie, were introducing Alberta to the strip mall. They would land anchor tenants such as banks and grocery stores, which would help them get financing and snap up land. They would go on to develop other commercial sites around the city, and expand their real estate empire through the West and south to California, Arizona and Texas. Mr. Singer was reported as one of Canada’s richest men with assets worth more than $1-billion, and his generosity extended to Jewish groups, community associations and the arts.

But times weren’t always so good. In the mid-1950s, according to his biography, Ottawa started poking around in Mr. Singer and Mr. Belzberg’s finances on suspicion of tax evasion for failure to report income and property sales.

At the time, Mr. Singer believed “they had me cold” and worried he’d be sent to jail, leaving a wife and two young children at home.

A judge levied fines instead.

When not engrossed in business or family, Mr. Singer’s other passion was sports.

“My dad watched sports every day of his life,” Stephen said.

In 1959, a thoroughbred race horse he co-owned named Tyhawk set a world record over six-and-a-half furlongs at one minute 14.4 seconds at Turf Paradise in Phoenix. In 1960, Tyhawk won the Highlander Stakes at Woodbine Racetrack in Toronto, matching a course record of 1 minute 10.2 seconds over six furlongs on dirt.

Mr. Singer couldn’t have been more proud. Tyhawk was later inducted into the B.C. Horse Racing Hall of Fame, considered “possibly the top British Columbia sprinter of all time.”

Still, Mr. Singer had one great regret: never picking up a professional sports team, though he did try.

In 1997, he attempted to hand over $70-million to help buy the Toronto Blue Jays, but his dream of owning a Major League Baseball team was blocked by an old boys club of insiders who didn’t take kindly to his involvement in a 1982 lawsuit. Even though the lawsuit was filed by Mike Shapiro, who was previously thwarted, along with Mr. Singer, in their bid to buy the Kansas City Royals, baseball doesn’t like anyone involved in challenging the system – especially outsiders.

As then-commissioner Bowie Kuhn said at the time: “Baseball is quarrelsome enough. It doesn’t need people with a propensity for litigation.”

“All that stuff, it happened 16, 17 years ago,” Mr. Singer told The Globe and Mail during his failed attempt to purchase the Jays. “I was a witness [for Mr. Shapiro]. I didn’t shoot baseball.”

Still, baseball didn’t want him or his money.

Other failed ventures included an effort to bring an NFL franchise to Los Angeles, and another to buy the Empire State Building in New York. He also tried his hand with a Calgary-based energy company and ended up flushing $75-million down dry holes.

But he famously wound up with a movie studio, thanks largely to serendipity.

In 1981, he was golfing in Palm Springs when he was asked if he was interested in touring Mr. Coppola’s movie studio, where the director of The Godfather films was shooting One From The Heart. He loved movies, so Mr. Singer tagged along looking for a signature, not a deal.

But he met the director, the pair hit it off, and soon Mr. Singer injected $3-million into the film. But it was an expensive box-office flop that pushed Mr. Coppola into receivership.

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