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Jim Doak with his long-time partner Patricia Best in Paris. ‘Jim was a gentleman, generous, classy and fun,’ she says.

Natalie Liconti

For Jim Doak, the proverbial glass was never half-full or half-empty. Rather, it was filled to the brim at all times, even when he encountered obstacles.

"Patsy, I'm just going to drive on," he was wont to say to his long-time partner, Patricia Best. An irrepressible optimist who parlayed a love for literature, languages, people and numbers into successful careers on Bay Street as an investment analyst, hedge fund manager and business commentator, he believed that as long as he kept moving and looking forward, things would get better. And the sheer force of his character usually made that come true.

"His optimism was a real gift," Ms. Best said. "Jim was a gentleman, generous, classy and fun. He believed in the best in everybody and gave people the benefit of the doubt long after others would give in. He gave his time and he was always pulling out his wallet to buy lunch or charity tickets or cookies from the neighbour's grandson who was selling them to raise money for something or another."

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Larger than life, with an omnipresent grin and a penchant for opera, folk music and anything by Cher, Mr. Doak sent his family and colleagues reeling when he died suddenly on April 22 in Ulan Bator, Mongolia. Mr. Doak, the chairman of Khan Resources Inc., was there with his colleague Grant Edey, the president and CEO. The small uranium exploration and development company had been at the centre of a long legal battle ever since the Mongolian government cancelled its uranium licence in 2009 and expropriated property it had planned to develop as a mine.

An international arbitration panel ruled in March that the government should pay Khan more than $100-million (U.S.) in compensation for its losses, and the brief trip began as a hard-hitting bid to collect payment. Instead, after the two men wound up negotiations on the morning of April 22, it turned tragic when Mr. Doak fell ill during lunch at the hotel and retired to his room to rest before their flight home. When Mr. Edey couldn't raise his friend on the phone, he had hotel staff open the door.

An autopsy performed in Toronto declared his death to be from natural causes related to the late-onset Type 1 diabetes Mr. Doak had been diagnosed with in his 20s. He was 59 years old.

"It's unreal," said Mr. Edey, who accompanied the body back to Canada. "He was a man who would weigh into any subject and he'd up his points with quotes from sources that range from the Romans, the Bible, prime ministers and philosophers. He was never at a loss for an answer and he was never at a loss for words."

Mr. Doak mischievously displayed his knowledge in an e-mail earlier this year to a firm of American lawyers representing Khan with a postscript to two of them who had been unable to attend the company's Christmas party in Toronto, referring to a comment British Major-General Sir Isaac Brock reportedly made as he led his regiments up Queenston Heights in the dark during the war of 1812 to repel American invaders: "Where are the damned Americans?"

The e-mail continued, "I hope after the tribunal's decision, you can quote your Commodore [Matthew] Perry from the same war – 'We have met the enemy and he is ours.'"

James Basil Charles Doak was born in Montreal on Sept. 10, 1955, the youngest of Kenneth and Barbara Doak's four children. His father was a high school science teacher and his mother was a homemaker; the family lived in a comfortable home in Saint-Lambert, a Quebec town on the other side of the St. Lawrence River, one of several communities that make up what is known as the South Shore. The family revelled in books, sports and music. Young Jim and his two older brothers and sister sometimes rode their bicycles down to the riverbank and jumped in, despite their parents' strictest instructions not to do so. He was a proud Boy Scout with multiple badges, and a good student who was part of the province's first French immersion school program in the 1970s – an experience that left him perfectly bilingual and in love with French culture.

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Jean-Claude Duthion, the former director of Toronto's Alliance Française, first met Mr. Doak, a long-time Alliance board member, when he interviewed for the job. The two soon became fast friends. "He was a man of great clarity who could quickly understand situations and sum them up elegantly in both French and English," he said in an interview from Washington, where he is now an educational attaché at the French embassy. "He represented this doubling of riches so well – truly a man of two cultures."

Mr. Duthion continued that he could think of no other person who so deserved the Légion d'honneur that Mr. Doak received from the French government last year – an award he was rightly proud of.

After beginning his studies McGill University, he soon moved to the University of Toronto, where he completed his Bachelor of Arts in economics and, despite an initial dream of becoming a history professor, embarked on a career in business. His first job was with a large stevedore company that had a branch in Saudi Arabia; for a few years, he helped manage the foreign workers and the company's trucking concerns.

Upon his return in the late 1970s, Mr. Doak got a job as an oil analyst with McLeod Young Weir, mostly because he was fluent in French and had worked in Saudi Arabia. A quick study with an even quicker wit and the guts to take on the country's clubby business elite, he never looked back, moving on from analysis into the management of other people's money.

Retired investment analyst Eleanor Barker recalled meeting Mr. Doak for the first time about 30 years ago, when the two were boarding a small plane to fly to Sarnia for a series of mine tours. She had spent hours poring over and preparing papers for the trip. He simply jumped on the plane, flipped through some papers and seemed an expert on the topic within minutes.

"He ended up asking the questions the whole day," Ms. Barker said wryly. "We were rivals and he called me his 'frenemy.' He was a great frenemy to have – and a great communicator who always had this twinkle in his eye when he was about to say something provocative."

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From 1997 to 2002, he was president of Enterprise Capital Management Inc., a Toronto-based investment firm, and then served as president of Megantic Asset Management Inc. until 2014. Recently, he co-founded a new fund company, Sui Generis Investment Partners LP. He also served as a director on a number of corporate boards, including the Quebec-based Cascades Inc., and was chairman of the Toronto Society of Financial Analysts and the non-profit Toronto French School.

In the late 1990s, Ms. Best, then editor of The Globe and Mail's Report on Business magazine, hired him to write an irreverent column. Later, he became a fixture on the Business News Network as a plain-spoken commentator who did not shy away from criticizing poorly managed companies, was always ready with a pithy quote and was unafraid of making predictions.

For instance, he recently said, "How can you forecast Stephen Poloz? He has put the random back in random walk."

And before the recent provincial election in Alberta, he declared: "Jim Prentice will be the next prime minister of Canada. This guy is smooth."

And during a debate on CTV back in April, 2012, he had this to say about Ontario NDP Leader Andrea Horwath's proposal to levy a 2-per-cent provincial tax increase on the rich: "It's nasty. It's ethnic cleansing. She's defining a group not by culture or language but by how much money they make and she wants to get rid of them."

The comment caused outrage, but Mr. Doak was unrepentant, even expanding on his comment in an op-ed published in the Financial Post a week later.

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"I wish my opposition was only the Ontario NDP but it is really [to] all those who want an easy fix, those who envy successful people with money, and those motivated by political greed," he wrote. "Like Visigoths wandering down the Via Aurelia into Rome, the Ontario NDP is in awe. It sees the shining bank towers and, well, it wants them. Its leader, Andrea Horwath, a former community worker, likely knows as much about the capital markets and the financial services industry as the Visigoths knew about marble plumbing and the Forum."

Zing! With his first wife, Daphne Ford Doak, he had four children – Laura, Alex and twins Natalie and Rosalind. He spent much of their childhood shepherding them to early morning hockey practices and ballet classes, and he coached soccer and T-ball teams. He also loved to take them camping, fishing, skiing – and to museums, galleries and the theatre. They were hard-core Montreal Canadiens fans, and NHL games were a part of their coming of age.

"[He taught us] that family comes first, to have strong principles and stand up for what you believe in, to always give back to your community and never stop learning," Laura Doak wrote in an e-mail. "He was a strong, principled man with a sharp mind, a big heart and a goofy sense of humour."

Ms. Best, with whom Mr. Doak became romantically involved after his first marriage ended, said that he delighted in bad jokes. Practically every time they went out for dinner, for example, they'd finish, the bill would come and then he'd announce to the server with grin, "OK, now we're ready to order dinner!"

In a Facebook post, his stepdaughter, Natalie Liconti, thanked him for being her editor, friend and a straight man who loved Cher. "Thank you for sitting through things you didn't sign up for and always being my voluntary, unpaid TA," she continued. "Thank you for our unspoken pacts. [And] thank you for giving my mother so much happiness and love."

Indeed, if Mr. Doak ever had a catchphrase throughout his life, it would have been: "I'm your biggest fan."

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He said it over and again to Ms. Best, to his children and stepdaughter, to friends and colleagues and countless others over the years. It illustrated his faith and confidence in them, and his wish to see them succeed.

Invariably, they thought the same of him.

Along with Ms. Best, his children and stepdaughter, Mr. Doak leaves his three siblings.

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