“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.”