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Kildare Dobbs.Linda Kooluris Dobbs

Satire was sparse in Canada in 1962 when Kildare Dobbs, an Irishman by way of India and Africa, published his first book, Running to Paradise. Stephen Leacock had been dead for more than 20 years, Mordecai Richler had yet to publish either The Incomparable Atuk, his detonation of Canadian cultural nationalism, or Cocksure, his salacious takedown of Hollywood film moguls.

Perhaps it was to encourage wit, keen observation and skilfully turned phrases that the judges that year for the Governor-General's literary awards ignored actual fiction, including Brian Moore's brilliant An Answer from Limbo, and instead honoured Running to Paradise, in a bizarre category, redolent of apples and oranges, called fiction and autobiographical writings.

Besides, they had reserved the non-fiction laurels for Marshall McLuhan's The Gutenberg Galaxy, a prophetic treatise on technology's power to shape communications and human behaviour.

Reading Running to Paradise, 50 years after its publication, constitutes more than an homage to Mr. Dobbs, who died at 89 of kidney and congestive heart failure in a Toronto hospice on Monday, April 1 – no joke intended.

The memoir of Mr. Dobbs's adventures in various parts of the former British Empire, with its title borrowed from his countryman, W.B. Yeats, is the first of his more than a dozen books.

It remains one of his best in the breadth of experience and the sharpness of his descriptions of human foibles and frailties, especially his own.

He is hilarious about his suspicious reception when he takes up a job as a schoolteacher in the early 1950s in a hamlet in Southwestern Ontario, which he calls Venice.

"There was no-one in sight, but the hair on the back of my neck bristled with awareness of Unseen Watchers," he writes of the taciturn inhabitants of the real town of Florence, named not after the Italian city, but the British heroine of the Crimean war.

Mr. Dobbs has his way with Ontario prudery and homophobia in a spoof about attending a gay orgy, and sends up the 1960s penchant for the "happiness" pill by describing a Christmas morning program he broadcast while stoned on drink and drugs. Two furious listeners objected to him referring to Westminster Abbey as "a national bone-house and television studio for royal appearances."

Not all of the pieces, many of which he wrote originally for broadcast or print in a relentless pursuit of a living wage, are played for laughs.

In Night Junction, we see him, a descendant of Irish gentry, serving as a lowly rating in the Royal Navy, sluicing his loneliness with drink in a wartime railway pub. An American G.I. "swaying gently," his "medalled tunic unbuttoned," appears without the usual props of "his" sort: "a gum-chewing girl" or a "hometown buddy."

The soldier, "alone with his money, his medals, his skinful of liquor," is desperate for friendship in a pub full of stony men hiding behind their broadsheets and their pints. He offers to buy a round and is repulsed with a "shocked flurry" of newspaper rattling.

In a few deft sentences, Mr. Dobbs has captured the niggardly British resentment of American largesse and disregard for decorum.

But the story doesn't end there. Mr. Dobbs steps forward and is joined by a Canadian, an officer in the Royal Canadian Air Force. They gently escort the drunken soldier to a grimy couch and then repair to the Canuck's room to drink whisky and exchange tales about books and writers. When the sound of the train pulling into the station interrupts their conversation several hours later, they wish each other luck and part – perhaps forever. Mr. Dobbs walks through the lobby, around the sleeping G.I., touching his cheek to check that it is still warm, and boards his train. "Sulphur fumes burned eyes and throat while I felt in pockets for ticket and papers. Soon I too would sleep."

Solitary journeys, befriending strangers and weird encounters were integral parts of Mr. Dobbs's life and career.

A man with a twinkle in his eye and an enticing Irish purr, he spoke so softly that listeners forced to lean in to hear his bon mots were often snared by his charm and his trove of historical anecdotes and literary allusions.

Although he had one vocation – writer – he lived in several outposts of Empire stretching over four continents, and he had many jobs: an official in the British Colonial Service in what was then Tanganyika (now part of Tanzania), teacher, travelling book salesman, book editor at Macmillan under the legendary stewardship of the late publisher John Gray, staff writer and editor at a series of now-defunct magazines from The Toronto Star Weekly to Saturday Night, books columnist at the Toronto Star, member of the editorial board of The Tamarack Review, and stalwart freelance writer and broadcaster for myriad venues.

His romantic life was a tangle and several of his love affairs ended in rage and recriminations, to the puzzlement of friends who only knew him as a genial and engaging conversationalist. But then the dire details of other people's domestic arrangements are often shrouded in platitudes.

At 58, he had the good fortune to meet and fall in love with Linda Kooluris, a painter and photographer half his age. Their interests, talents and personalities melded happily for more than 30 years and the publication of The Gardens of the Vatican, for which she took the photographs and he wrote the text.

She fell in love "with his brilliant and witty voice on the radio," as she worked at her drafting table when she was a freelance illustrator in Montreal. After she moved to Toronto in the late 1970s, she was "bowled over" by his prose.

They met late in 1980 at a farewell party for Mr. Dobbs, who was about to set off on a writing trip. He sent her a postcard from Rome: "It has been my experience that beautiful women usually have unworthy men in their lives. I want you to know that I am as worthless as the next guy."

Some might have run, if not to paradise, at least in the other direction, but she was charmed by his "big heart" and within a few months they were married.

As Mr. Dobbs wrote in 2005 in Running The Rapids (a final memoir that narrowly escaped foundering on editorial shoals): "I married three times, first when I was just 21 during World War II, committing to life at a time when foresight was impossible. Two sons were born to us before we parted after 10 years. The second marriage lasted 13 years, with two daughters. The third marriage will last my time."

And so it did, with Ms. Kooluris Dobbs elevating the wifely definition of help-mate to celestial reaches.

Kildare Robert Eric Dobbs was born on Oct. 10, 1923, the first son after several daughters for Evelyn and Maud Dobbs. Irish Protestant gentry, the Dobbs family was well placed in the Church, the academy and British Colonial administration. Mr. Dobbs was acting commissioner in Meerut, Uttar Pradesh, when his son Kildare was born.

The family's decline echoed the Empire's, with several illustrious members slaughtered in northern France and Flanders in the First World War and others falling afoul of affirmative action in the Raj, and the inevitable rise of local talent in the Indian bureaucracy.

The senior Mr. Dobbs found himself retired at 50 and living with his large family in a world he barely recognized back in Dublin. When women were invited to join one of his luncheon clubs, he resigned in indignation.

From a childhood of servants, lush gardens, nights interrupted by whooping hyenas, prowling leopards and tigers, and daily rides on the family's government-issued elephant, Kildare and his younger brother, Bernard, grew up in lessened circumstances in Dublin and the traumatizing effects of British boarding schools.

Although Ireland was officially neutral during the Second World War, Mr. Dobbs enlisted in the Royal Navy in 1941 and survived both German submarines and hurricanes on convoy duty in the Atlantic.

As a married veteran and father of two sons, he went on scholarship to Jesus College, Cambridge.

Like his father before him, he took his family to the colonies in 1948, signing on as a teacher and then a district officer in Tanganyika in East Africa. Things went horribly wrong in the African twilight of Empire, not only in neighbouring Kenya, where the Mau Mau rose up against their imperial masters, but for Mr. Dobbs personally. He was charged and convicted of shooting an elephant and confiscating the animal's mammoth ivory tusks for his own gain, rather than the government's profit.

Whether he was set up by a mendacious superior, was a dupe of native profiteers or was guilty is murky at this distance, but the incident, which led to a prison term of several months, haunted Mr. Dobbs for many years. He turned the experience into fiction in Pride and Fall in 1981.

A review by William French in The Globe and Mail praised the novella for catching "the mood of decadence, the sense of inevitability and futility that seemed to prevail" and the author for the way he "effectively contrasts tribal customs and civil service protocol" and ends the story with "an unexpected moral twist."

Humiliated, and dependent on his father's grudging generosity, Mr. Dobbs set out, after his release from prison, for another outpost – Canada – where he made his way in a largely untilled cultural landscape.

For the most part, the country and the writer suited each other, which is more than can be said of most relationships stretching more than half a century. In an unforgiving occupation, Mr. Dobbs never surrendered to the regular paycheques offered by advertising agencies and public relations firms, earning his cultural capital in literary awards and membership in the Orders of Ontario and Canada.

He published his last book, Casanova in Venice: A Raunchy Rhyme, in 2010. He was 87.

The last three years were tough as his health declined and his kidneys and his heart faltered. The spirit didn't flag, though, even when he decided late in March that it was time for palliative care.

"I understand they'll give you anything you want there," he remarked to a friend. "I will tell them I want gin," he said with his trademark half-chuckle. And then he added: "With apologies to Dylan Thomas, I have no intention of not going gentle into that good night. I want to go as gently as possible, with no pain."

And that's what happened, with the help of caring doctors and nurses and the ministrations of friends and his wife, Linda, who arranged for music and song to soothe the way.

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