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Far from a mere corporate suit, Ron Osborne loved literature, golf and karaoke; Lady in Red was a particular favourite.© Mike Cassese / Reuters/Reuters

The man credited by many as one of the best corporate directors in Canada and the smartest person at the boardroom table was also the first to say he had a stupid question.

Ron Osborne, a widely respected executive, courted to serve on boards that spanned the landscape of Canadian business – from Sun Life to Tim Hortons to Postmedia – was known for an incredibly sharp (some say "brilliant") intellect, a tough and outspoken personality and a habit for self-deprecation.

Those who sat on boards with him were accustomed to his preambles, which would always come before an insightful question or the kind of surgical analysis that cut clean to the core of a business issue: "I might have lost the thread here, but …," he'd say, or "this is probably a dumb question but I'm going to ask it anyway."

"It was never a dumb question," said Paul House, chief executive officer of Tim Hortons Inc. "He was going to probe – that's what makes a good board member."

Mr. Osborne died in his sleep on the morning of April 9 at his home in Florida, the result of coronary artery failure. He was 66.

Trudy Eagan, a former executive at Sun Media, served on the board with Mr. Osborne in the eighties, after cable and publishing company Maclean Hunter Ltd. took a majority stake in the newspaper chain. She recalled his dedication to know everything there was to know about every company he was involved with.

"Preparing for board meetings, you did all your homework and felt you were ready for any question that might arise. Ron always managed to find that one question that had us all scrambling," she said. "He was a very diligent board member. So wise."

This extended to every facet of the business -- when the Financial Post was transferred to Sun ownership and went from a weekly to daily publication during his tenure, Mr. Osborne counselled against cutting out crossword puzzles to make editorial space. And he was a quick study: when he took over the top job at Ontario Power Generation in the late '90s, he took his friend Paul Godfrey for a tour of the Pickering power plant. The chief executive officer of Postmedia Network Canada Corp., who studied chemical engineering, recalls that the man who began as an accountant could have fooled anyone into thinking he had a degree in nuclear engineering.

His interests went well beyond business – his friends and colleagues call him a "polymath" and "a true Renaissance man." He was a lover of music, literature and history, an enthusiastic and good-humoured golfer, even when he botched a shot, an admirer of cars with big engines, and a lover of travel who spoke four languages.

"He was brilliant. He was my role model, my adviser," said Postmedia CEO Paul Godfrey, who recommended Mr. Osborne to the RioCan board and more recently brought him on as chairman at Postmedia. "There isn't a better CEO, a better board member in Canada. … There's almost no such thing as an irreplaceable person. Ron Osborne is the closest thing."

Ronald Walter Osborne was born May 11, 1946, in the seaside town of Worthing, Britain, about 96 kilometres south of London in West Sussex. His parents, Frederick and Annie Osborne, were grocers. He has one younger sister, Christine.

After graduating from Collyer's School in Horsham,Mr. Osborne studied French and German at Cambridge, receiving a BA in 1968. The following year he married Grace Snead, an Alabaman he met while she was on vacation in England. They celebrated their 44th anniversary last month.

Mr. Osborne immigrated to Canada after seeing a wanted ad for the accounting firm Clarkson Gordon & Co., which was offering jobs in Toronto. He advanced quickly, moving his young family to Rio de Janeiro as a partner in 1976 for a three-year stint that he and Grace always remembered fondly.

He stayed with the firm until 1981, when his acumen drew attention from executives at media company Maclean Hunter Ltd., owner at the time of cable TV services and publications, including Maclean's magazine and the Financial Post. He was hired on as chief financial officer, made president at the age of 38, and CEO two years later.

When Maclean Hunter took a majority stake in the Sun Media chain of newspapers in the early eighties, Mr. Osborne was one of just two MH executives who took a seat on the Sun board. But the somewhat rowdy group of journalists who expected a bean-counter type from the accountant in their midst were soon proved wrong.

"He wasn't just a numbers guy. He was a leader," said Lionel Schipper, who later recommended Mr. Osborne for a spot on the Four Seasons board.

"It's not easy, when you're dealing around the table with Peter Worthington and [Doug] Creighton and people like that. He fit in immediately," recalls Herb Solway, counsel and founding member of Goodmans LLP and a director at Sun Media at the time. "We were surprised how much we liked him. Here someone's taking over the company… . He had an accountant's mind but not an accountant's charm. He was very charming and very likeable."

He loved karaoke so much he had his own setup at home, and would host dinner parties capped off with some time at the mic. At parties where karaoke was involved, he was a standout: Lady in Red was a favourite tune. When not singing, his laugh would reverberate through gatherings.

"He was often the life of a party at the Sun events," Mr. Godfrey said. "Directors usually leave that to the staff, but Ron was always the type of guy who could fit in in any crowd."

Mr. Osborne oversaw the $600-million acquisition of Selkirk Communications Ltd., which strengthened the company's cable assets. Maclean Hunter's strength in cable would eventually attract the eye of Ted Rogers.

But even the takeover bid failed to dampen Mr. Osborne's spirits. As the Globe and Mail's Gordon Pitts wrote in his book Kings of Convergence, after Rogers announced its intention to bid on the company, both executives attended the annual Brazilian Ball in Toronto. There, Mr. Osborne and his group at Maclean Hunter had a faux theatrical poster made, advertising a show called The Phantom of the Offer, with references to the legal and investment advisers in the Rogers camp. They walked the poster by the Rogers table for a bit of fun amid the tension.

Mr. Rogers eventually succeeded, buying the company for $3.1-billion and splitting up some of the cable assets with Shaw Communications Inc.

The deal done, Mr. Osborne went before the country's broadcast regulator to advocate for the acquisition he had fought. He then moved on to Rogers rival Bell Canada, where he took up the post of CEO briefly before accepting the top job at Ontario Power Generation Inc. in 1998.

It was there that he navigated the most difficult and disappointing post of his career. He was charged with bringing the troubled Pickering nuclear plant back to full operation, but the job was marred by cost overruns and conflicting government messages about privatization plans. Though he offered to resign, he was asked to stay on – only to be ousted in late 2003, along with two other executives, in a public move by the new Liberal provincial government.

He remained a well-respected figure on Bay Street, however, and within two years was named chairman of the board of Sun Life Financial Inc., where he had served as a director for years.

People were forever recommending Mr. Osborne for board appointments because of the value he brought to the table, his colleagues recall. Those included Torstar Corp., Four Seasons Hotels Inc., Tim Hortons Inc., RioCan Real Estate Investment Trust and Shell Canada. Reflecting his deep interest in the arts, he also served on the boards of Roy Thompson Hall and Massey Hall in Toronto, and the Shaw Festival in Niagara-on-the-Lake.

"I can certainly speak for RioCan that he made us in his nine years on our board a far better company, and myself a better CEO," said Edward Sonshine. "In his humorous and respectful manner, he elevated our processes, transparency and our whole manner and method of making decisions."

Even after difficult meetings at some companies, he was remembered for taking the time to stop by a corner office with an encouraging word.

"He engendered great loyalty because he was such a good and loyal friend; and great respect because he was so remarkably good at all he did," said Robert Prichard, chairman at Torys LLP and former CEO of Torstar Corp.

Mr. Osborne was a tender grandfather to two-year-old Lucy, and just before he died, he had the pleasure of meeting his first grandson, Dillon, who is one month old. He has three children; David, a musician, Charlotte, who works in advertising at Toronto agency Bensimon Byrne, and James, a postdoctoral fellow in archaeology at Johns Hopkins University.

In recent years, he and his wife had sold their house in Toronto in favour of a condo, to make it easier to spend time at their home in Florida – where he golfed at the Country Club in Delray Beach – and at their cottage in Muskoka, while still serving on boards.

In Florida, his sense of humour had quickly made him friends at the golf course. "He was suddenly the big man on campus," Herb Solway said, adding that it hardly surprised him.

"Ron was always happy. He had that optimistic outlook," he said. "There was always a twinkle, and a laugh. His eyes were sparkling. He was alive."

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