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A group of Toronto Telegram city hall reporters, including Don Obe in shirtsleeves on the right, ham it up in the city council chamber.

Courtesy of Lynn Cunningham

Gruff of mien, blunt of speech and with eyebrows that spoke a language of their own, Don Obe was a journalist of the classic, crusty old school: a hard-working, hard-drinking and hard-living teller of stories.

And if he weren't surrounded by a halo of tobacco smoke, it was probably because he had misplaced his own package of cigarettes and was coming to cadge one, or six, from others.

As a newspaper writer, then editor at Maclean's, The Canadian and Toronto Life, Mr. Obe, who died on Nov. 7 of a heart attack in a Toronto hospital while being wheeled on a gurney to a medical test, didn't always follow the rules.

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Sometimes, he had a concept and a headline that he wanted a story to fit. He loved to draw readers in with something at once clear and opaque, something in the tradition of "Frank Sinatra has a cold," the title of Gay Talese's famous profile of the singer in Esquire magazine.

After graduating in 1959 with a diploma in journalism from what is now Ryerson University, Mr. Obe thought he would spend no more than a decade working for newspapers before quitting to write the great novel.

"You'd get your speed down, your style down [and] pay off your debts," he recalled in an interview with Bill Reynolds, director of the graduate program in Ryerson's journalism department.

Then Mr. Obe discovered the literary journalism that was so prevalent in the 1960s and 1970s, in which writers such as Mr. Talese, Tom Wolfe and Hunter Thompson filtered their reporting through their own impressions.

"You could stay in journalism and get the artistic satisfaction," Mr. Obe explained in that same interview. "You could experiment, you could write in your own voice. You could write stories."

And he did. Through stints at The Vancouver Sun and Toronto Telegram, he honed his craft, garnering notes from editors that read "Good stuff, kid" and National Newspaper Award nominations for stories on subjects such as Quebec's Quiet Revolution.

Then, fingers poised over his typewriter, he froze. It was writer's block and it turned him into an editor and mentor of others.

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"People believed in him," said Globe and Mail columnist Roy MacGregor, who first met Mr. Obe at Maclean's magazine and went to work for him at The Canadian, a weekly insert for newspapers across Canada that featured some of the best writing in the country.

"Don had this Jack Kerouac side to him. He could talk writing the way others talked hockey or girls," Mr. MacGregor said.

Mr. Obe went to the wall for his writers, refusing to cave to outside pressures, no matter how powerful.

Mr. MacGregor recalled an article he wrote in 1977 for The Canadian about then-transport minister Otto Lang's political missteps, such as an attempt to have his family's nanny fly home to Scotland for free on a government plane. When Mr. Lang received an advance copy by accident, he tried to get an injunction to prevent the story's publication and filed notice of a libel lawsuit. To make matters worse, two newspapers in Saskatchewan, Mr. Lang's home province, announced they would never carry the magazine again.

"I was 28 and trying to make it in the business and here I was, slapped with a lawsuit from the minister of transport," Mr. MacGregor recalled.

"Don called me in for a meeting and said 'We don't back down. We stand by our story.' And then he asked, 'Are you sure of your facts?' I don't know what I would have done if he hadn't have backed me all the way."

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Don Obe was born on March 1, 1936, in Brantford, Ont., the eldest of George Obe and Mabel Willson's five children. His father, a Mohawk from Oka, Que., was a welder, as were two of his three brothers. To help make ends meet, his mother worked at the local hospital and in a factory that made electric blankets.

Young Don was a talented athlete who could play all manner of sports and was quarterback of his high-school football team.

But he was ambitious, a dreamer who was bigger than the bounds of his home town; he yearned to escape, experience the world and come home occasionally to entertain the family with his adventures.

"When he was at The Vancouver Sun, I remember him rolling into town with a buddy of his named Tiny," said his brother George Obe, who was born 18 years after his eldest sibling. "They'd driven from the West Coast in a '49 Oldsmobile and they told me all sorts of stories from the road. I was 9 or 10 at the time and I thought this was fantastic."

After graduating from Brantford Collegiate Institute and Vocational School, Mr. Obe worked two jobs to scrape together tuition for the journalism program at Ryerson, which he completed in 1959. His first job was as a correspondent in the mostly rural Chatham bureau of The Windsor Star.

He never looked back, and he rarely compromised. As associate editor at Maclean's under Peter Newman, Mr. Obe was wont to explode, announce he was quitting and stalk out the door – once over the removal of the word "booze" from a story because it was deemed too racy.

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As editor of The Canadian, he once called Mr. Macgregor back to Toronto from Winnipeg, where the young writer was covering a golf tournament.

"Why?" Mr. MacGregor asked. "Because we need you," Mr. Obe replied.

At the time, their press softball baseball team was in the playoffs and the editor, who played first base, wanted his catcher to be behind the plate the next evening to take on the much reviled Toronto Star. After the game, Mr. Obe flew Mr. MacGregor back to Winnipeg, all expenses paid.

At one point, however, The Canadian's owner, Torstar Corp., decided the magazine needed to focus solely on Canadian heroes, which made Mr. Obe quit and take on the top job at Toronto Life magazine.

In 1981, he stepped down from Toronto Life because, after years of editing, he wanted to write again.

Among his projects was a short-lived media column for the magazine; he won a National Magazine Award for one column called "The Dissident Rabbi," about Reuben Slonim, a former Toronto newspaperman turned rabbi who believed Israel could survive only if it revived the spirit of fraternity, justice and reconciliation as preached by the prophets.

But, as Mr. Obe told Michael Thomas in the summer 2013 issue of the Ryerson Review of Journalism, his writing was rusty and after a breakup with his first wife, Sheila Gormley, he was broke.

In 1983, he landed at his alma mater as the head of the Ryerson's school of journalism, back in the familiar roles of teaching and mentoring. At the same time, he started the review; the first issue appeared at the end of the spring term of 1984.

He retired from Ryerson in 2001, becoming a professor emeritus.

David Hayes, who took over the column at Toronto Life and would become an instructor at Ryerson, said he had Mr. Obe review his own writing and relied on him for advice.

"He had so much experience and wisdom, an uncompromising attitude and a passion for great writing," Mr. Hayes said. "Long after he retired, I would call him up for an ethics consult or other problems because I knew his advice would be solid."

Throughout Mr. Obe's life, drinking and carousing played a big role, often bigger than it should have. He wasn't a belligerent drunk but he could put away massive quantities of wine and alcohol without blinking – two bottles of wine at dinner, endless drinks with his cronies at a local bar. He was from the generation of liquid lunches, afternoons and evenings. And although he quit drinking after his retirement from Ryerson, by 2003 he was at it again.

It wasn't unexpected. In 2002, his only child, daughter Kira, long a troubled soul, died from an alcohol and drug overdose.

A decade earlier, his young grandson Andrew, who was born with fetal alcohol syndrome, came to live with Mr. Obe and second wife, Lynn Cunningham, a writer and instructor at Ryerson.

Ms. Cunningham was adamant that they take care of the boy. Her husband wasn't so sure. He was never good at domestic chores, never mind relationships or caring for someone who depended on him.

"Don was well into his 50s and suddenly, we had a tiny kid in the house," she recalled. "To care for him effectively, we had to spend a great deal of time educating and advocating for him."

The couple split up, although they remained on friendly terms and never divorced. Andrew remained with Ms. Cunningham; he is now in college and studies independent music production.

Mr. Obe leaves Ms. Cunningham, three of his siblings and his grandson.

Mr. Obe survived two bouts of cancer and was battling non-Hodgkin's lymphoma at the time of his death. After episodes of absentmindedness, he was told last fall that he had dementia, a diagnosis that upset Ms. Cunningham more than him.

"Things were going so well at the time. He was living his life on his own terms, most of the time was not in any real discomfort," she said. "But it didn't seem to be an issue for him, what potentially lay ahead.

"I hope that a whole lot of people he taught will replicate his enthusiasm for good non-fiction writing," Ms. Cunningham continued.

"Given that he died around Remembrance Day, he's like the cenotaph of what once was in the world of journalism – if it isn't still."

Editor's Note: An earlier version of this story incorrectly said Mr. Obe and his wife Lynn Cunningham got custody of Mr. Obe's grandson Andrew in 2002. In fact, it was in 1992.

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