Oleson made world more interesting

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Longtime Free Press editorial writer Tom Oleson, who died Thursday morning at 66, left a legacy of erudite, forthright opinions expressed in well-chosen words.

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The Winnipeg Free Press lost one of its most fearless voices - and one of its most loyal friends -- Thursday. Longtime editorial writer Tom Oleson died in hospital just after dawn. He was 66 years old.

In his wake are a lifetime of well-chosen words, polished sentences and great stories. He was at the Free Press for 45 years, and there's a story behind each and every one.

It started almost by accident. Oleson was born a professor's son in 1946 and grew up buried in books. After graduating high school, he enrolled at the University of Manitoba, where he studied archeology and anthropology.

He might have stayed on that academic path, but his mother Elva had a friend who worked for the Free Press and thought that Tom might be well-served by meeting him. So in 1967, Tom landed a job as a copy boy. Within months, he was hooked: Although he took a brief sojourn to Europe and back to university, he "clung to (the Free Press) like a barnacle," he wrote last year.

Two years after starting, Oleson was promoted to the foreign desk, where he bonded with former Free Press editor Bob Saunders -- the "grandfather he never had," Tom's cousin, Bob Oleson, recalled. Under Saunders's wing, Oleson learned the newspaper biz inside and out and began to hone his strong and distinctly literary voice.

Over time, Oleson would hold a number of positions within the paper, including literary editor. But he was best known for the editorials and columns he wrote after being named literary editor and a member of the editorial board in 1974.

The sum total of those writings is challenging. Nothing was hidden from Oleson's purview: He wrote about everything from cosy Winnipeg watering holes to daunting foreign boondoggles, Berlusconi to Bellamy's Restaurant. He thrived on politics and delved deeply into poetry. But whatever he wrote, he penned with a certain self-effacing humour and sharp, acerbic flair.

True, Oleson's opinions didn't always land on the right side of history -- for instance, many in Winnipeg still remember the sting of his 1990s columns critiquing same-sex marriage, though recent columns on the subject showed he had long since changed his view.

Most importantly, whether readers agreed or disagreed, Tom held his job with the gravity that it was due: He never shied away from what he perceived to be the truth. His dad was a straight-shooter; Tom Oleson was certainly that, too.

"Tom was a gifted writer, but he was also fearless," said Free Press comment editor Gerald Flood, who worked with Oleson for 15 years. "He had no qualms about being politically incorrect, and what he believed, he believed fiercely."

On that note, his last column for the Free Press, an April 28 call to continue debating abortion law, left little doubt on which side of the debate he stood. "(Tory MP Stephen) Woodworth's motion may be hopeless, but it does not have to be useless if it can unlock the shackles of political correctness that have bound us for so many years," he wrote. "We should be able to debate publicly about abortion without one side being damned as dinosaurs and the other evangelized as angels."

Tom was no angel either, and he'd insist on the unvarnished truth in an obituary. He suffered from depression, did not take good care of his health and once mocked those who claimed problems were really opportunities by writing that meant he had an opportunity with alcohol.

His colleagues on the Free Press editorial board were optimistic when he recently was admitted to hospital, hoping it would help him get his health on track. It was not to be: He died at 6 57 a.m. Thursday of multiple organ failure.

There had been hard knocks in recent years. In March, after 32 years of marriage, Tom buried his wife Laurie, who died suddenly of a stroke; she'd been battling terminal cancer. Two years earlier, in March 2010, the couple's son Kristofer was killed in a tragic accident at the age of 24. Oleson captured the loss of these two loves in a poignant column on April 15, one in which he quoted Rudyard Kipling and British rhymester Harry Graham. It was a beautiful piece of writing. With Tom, it usually was.

It was family first with him, Bob Oleson recalled, and intellectual curiosity second. He had a wicked sense of humour and was a regular at the old Winnipeg Press Club, where he'd keep his fellow journalists laughing long into the night. (It was also, memorably, where he met his wife.)

"In some ways, Tom is the end of an era," Flood said.

Tom lives on in the hearts of his two sisters, his cousins, his children -- daughters Kaitlyn and Jennifer, sons Michael and Kristjan and stepson Michael -- and his grandchildren.

At the Free Press, friends and colleagues remember a mentor and editor, and most of all a gifted writer committed to his craft. In recent years, he moved quietly amongst us, ready with a nod and a kind word about a story or a sentence or a lede.

And, of course, Tom will be remembered by thousands of readers, many of whom probably hated to love him.

"There were," Bob Oleson said, "a lot of happy times."

Those happy times live on best in Tom's own words, in the columns that increasingly turned to his family and friends and to the joy he took in watching the next generation spread its wings and take flight. It was a generation he often thought of -- and often with the distinct hint of an otherwise uncharacteristic pride.

"The baby boomers' legacy consists mainly of a considerable financial burden for our children and the coming society to bear, or so our heirs might think," he wrote on New Year's Eve 2010. "But as we fade away, we can take solace in the fact that if we didn't actually leave the world a better place, we left it a far more interesting one."

Republished from the Winnipeg Free Press print edition May 18, 2012 A12