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George Taylor Richardson ran the family business for nearly three decades.

On a business trip to Rotterdam back in 1954, George Taylor Richardson found himself being taken on a short flight in a helicopter. For the 30-year-old scion of the Winnipeg-based grain and securities empire James Richardson & Sons Ltd., it was love at first sight. Utterly enthralled by the experience, he obtained his pilot's licence, acquired a small chopper and took to the skies.

Throughout his life, Mr. Richardson, who died of natural causes at the age of 89 on May 14, flew himself all over the country by helicopter instead of relying on the more traditional forms of transportation available to wealthy business owners, such as chauffeured limos and private jets.

He would rely on the low-flying, versatile vehicle for fact-finding missions – checking out the crops and rail spurs and prairie grain elevators that formed the backbone of JRSL's sprawling business. And he'd use his chopper to get to his office in the Richardson Building in downtown Winnipeg, as well as the family cottage on a Lake of the Woods island.

But perhaps most significantly, Mr. Richardson regarded his helicopter as a means of exploring Western Canada and the North. "He loved just getting in the helicopter and picking a destination," says his son Hartley Richardson, who describes his father as relentlessly inquisitive and curious about the world.

Those journeys didn't always go smoothly. According to a commissioned biography published in 2010, Mr. Richardson, his wife, Tannis, and another couple once flew from Winnipeg to Churchill, Man., a remote community on Hudson Bay. On the way back, they flew into a wall of bad weather and had to make an emergency landing on an isolated patch of tundra.

Instead of radioing for assistance, Mr. Richardson dug out emergency provisions and found some firewood, and the four middle-aged adults camped out overnight. The weather was still dodgy the next day, however. As soon as the clouds broke slightly, Mr. Richardson tossed all the unnecessary objects off the helicopter and powered the vehicle up toward clearer skies.

"We used to say he had a PhD in common sense," says Chuck Winograd, who worked for JRSL's securities division for 27 years before assuming senior leadership positions with the Royal Bank of Canada. "He was a very logical guy who had a good feel for things."

Western Canadian royalty

Born in Winnipeg on Sept. 22, 1924 to James and Muriel Richardson, George was part of the fourth generation of a family that had dominated Winnipeg's business community for decades. "Mother always said I was born with a cigar in my mouth and a gear shift in my hand," he told biographer Tim Higgins.

Like Montreal's Desmarais clan or the Irving family in New Brunswick, the Richardsons are like royalty in Western Canada, says Mr. Winograd. According to a Canadian Business magazine ranking in 2013, their net worth is $4.45-billion, making them the ninth-richest family in Canada.

JRSL traces its roots to Kingston, in 1823, which was when James Richardson arrived in Canada as a 4-year-old from northern Ireland. He set himself up as a grain merchant in 1857. In the 1890s, the company relocated to Winnipeg's Grain Exchange, where it managed a far-flung trading and exporting empire that included the iconic Pioneer grain elevators located across Western Canada and in key ports such as Thunder Bay and Vancouver.

By the Depression, the company had a customer base of more than 55,000 farmers, and later established a radio station, an airline (later known as Canadian Airways, the country's first commercial carrier) and a securities division to help Western Canadian firms raise capital.

Named after an uncle killed in France in the First World War, Mr. Richardson – the third of four children – excelled in both sports and academics at Winnipeg's Ravenscourt School for Boys.

Mr. Richardson knew if he wanted to get a university degree, though, he would have to pay his own way. So he bought several head of beef cattle, rented some pasture land and gradually sold the growing herd to generate the funds he needed.

Despite that entrepreneurial start, he didn't do especially well in his first year in commerce at the University of Manitoba. In 1942, the following year, he transferred to Queen's University, in Kingston, but was promptly sidelined after he crushed several vertebrae playing rugby.

Mr. Richardson spent four months in a body cast recovering from surgery, and many more recuperating in Winnipeg. His elder brother James – later a cabinet minister in the Trudeau government – enlisted in the armed forces, but the back injury prevented George from following suit.

It was a tumultuous period at the company: James A. Richardson, George's father and the head of the family business, died unexpectedly in 1939. His funeral drew thousands of mourners and made headlines in Winnipeg. But when it ended, the Richardson family had to figure out what to do with the company. Against the advice of her advisers, Muriel, George's mother, took the helm, becoming the first woman to run a major Canadian corporation.

In 1946, after he'd completed a commerce degree, George Richardson went to work for JRSL. He spent one summer working in menial jobs at Pioneer's massive grain elevator in Thunder Bay, Ont., but soon became Muriel's "eyes and ears," travelling extensively to check up on the company's domestic and international operations.

Two years later, he married Tannis Thorlakson, the daughter of a prominent Winnipeg surgeon and a member of Manitoba's large community of Icelanders. They had four children: Pamela, David, Hartley and Karen.

At the height of the Cold War, JRSL, working through a client of Richardson Securities' Hong Kong office, landed a $20-million grain sale to China, ending a long-standing ban by the Communist government on Western imports.

George Richardson, who had overseen the development of the Richardson office tower at Portage and Main, was appointed president in 1966 (brother James was named chairman at the same time), and soon began focusing on a plan to repatriate the venerable Hudson's Bay Co., which, despite its chain of prime retail locations, was still chartered as a British corporation, with its board based in London.

It was more than just a business deal. From childhood, Mr. Richardson had known how to work a trap line on his family's farm, catching mink, ermine and even coyote, according to journalist and historian Peter C. Newman. Mr. Richardson, according to his biographer, had even tried to sell skins to a Hudson's Bay Co. "raw fur warehouse."

During negotiations, Mr. Richardson devised a plan to have his company's securities division buy large blocks of Hudson's Bay Co. shares in the U.K., break them up and sell them to Canadian investors. He also insisted that the archives be transferred to Canada. It was a herculean task, Mr. Newman points out, which involved shipping almost 70 tonnes of files to Winnipeg.

Once the deal was consummated, on Hudson's Bay Co.'s 300th anniversary, Mr. Richardson became its first Canadian governor. He'd fly to remote trading posts and even commissioned the construction of a replica of an early company ship, the HMS Nonsuch. Mr. Richardson also oversaw the expansion of the chain, acquiring Zellers and then Simpsons, the chief rival to Eaton's in Eastern Canada.

But he didn't hold the position for long: In 1979, newspaper baron Ken Thomson and his senior adviser John Tory Sr. orchestrated a takeover bid; the Richardsons ultimately sold their holdings, for $38.50 per share.

George Richardson (or "GTR," as he was known inside the family business) took a highly pragmatic approach to sustaining and growing the company. As a manager, Mr. Winograd says, he eschewed the role of the remote CEO. "He was always around. He didn't know the difference between people. To him, the Queen of England and someone working in the cafeteria were the same person. He just had an affinity for people."

Joe Martin, an expert in Canadian business history at the University of Toronto's Rotman School of Management, points out that Mr. Richardson carefully steered the private company, successfully avoiding the family feuds and commercial implosions that afflicted clans such as the Eatons and the McCains.

"What's the old saying? From shirt sleeves to shirt sleeves in three generations. Well, they're hardly in shirt sleeves now."

Time for tough decisions

Mr. Richardson never seriously considered taking the company public, Mr. Winograd says, and made difficult corporate decisions at times, such as moving Richardson Securities (later Richardson Greenshields, the last of Canada's large independent brokerage houses, which was acquired by RBC Dominion Securities in 1996) from Winnipeg to Toronto in the 1980s. "That's where the talent was, so [the move] had to happen," Mr. Winograd says. "His head was in it, but his heart wasn't. He couldn't understand why things couldn't be operated from Winnipeg. It wasn't something that made him happy."

After Mr. Richardson retired as CEO in 1993, Hartley Richardson says, he would "watch for rocks" from the bow of the corporate ship, but never attempted to second-guess his son's decisions. "He knew I had to make some of my own mistakes."

Mr. Richardson's track record as a deal maker wasn't flawless. In 1998, he triggered a legal battle with Albert Cohen, another Winnipeg businessman, over a $39-million offer to buy part of an oil and gas company. In court, Mr. Cohen alleged that Mr. Richardson had tried to back out of the hand-shake deal after a dispute over the value of the offer. A trial judge agreed, and Mr. Richardson failed to overturn the decision on appeal.

About a decade ago, Mr. Richardson, then in his late 70s, decided to locate a Canadian Airways Fokker bush plane that belonged to his father, and which had gone down without a trace in Charron Lake, in Manitoba, in the 1920s.

With a team of divers and naval equipment, Mr. Richardson found the so-called "ghost of Charron Lake" and salvaged the fuselage, which was completely in tact. "That was Dad," Hartley Richardson says. "He was damned determined he was going to find that plane, and he did."

Mr. Richardson is survived by his wife, Tannis; sons David and Hartley; sister, Kathleen; and nine grandchildren. He is predeceased by daughters Pamela and Karen.

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