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Allan Slaight.Rene Johnston/The Canadian Press

Allan Slaight, Canadian media magnate, rock ‘n’ roll radio pioneer and significant arts philanthropist, had a twinkle-eyed enthusiasm for gamesmanship, with fellow legendary radioman Jack Kent Cooke often on the receiving end of his elaborate ploys.

At the end of the 1950s, the well-established Mr. Cooke owned CKEY, while young Mr. Slaight was the program director at 1050 CHUM. The two stations were Top 40 competitors in the lucrative Toronto market. Mr. Slaight once floated rumours that CHUM was switching from playing rock ‘n’ roll to something more traditional. Promotional spots hinted at a format change: “Stay tuned for the sweet swingin’ sounds of CHUM.”

Then, fully aware that Mr. Cooke listened to competing stations, Mr. Slaight had disc jockey Bob Laine play Glenn Miller’s A String of Pearls on air, ostensibly for an audience of one – Mr. Cooke, who subsequently switched CKEY’s playlist to saccharine, string-laden music in response. He thought he was getting the jump on Mr. Slaight and the nemesis CHUM.

It was a ruse, though. CHUM was sticking to rock. It took weeks before Mr. Cooke realized he’d been hoodwinked into delivering the sock-hop audience to CHUM. “Allan could be quite mischievous,” said David Ben, who wrote the 2013 biography Slaight: Off Hand. “And he especially loved to torment Jack.”

Mr. Slaight died of natural causes on Sept. 19 at his home in Toronto. He was 90.

Mr. Slaight went on to become a broadcasting mogul who was part of the syndicate that rescued the fledgling Global Television network from financial calamity in the mid-1970s.Tibor Kolley/The Globe and Mail

Beginning his career in 1948 as a cub reporter at a station his father owned in Moose Jaw, Sask., Mr. Slaight went on to become a broadcasting mogul who was part of the syndicate that rescued the fledgling Global Television network from financial calamity in the mid-1970s.

At Global, Mr. Slaight trimmed expenses – “sell more than you spend,” was his simple business credo – and commissioned what became a cult-classic comedy series, Second City Television (SCTV).

In 1977, Mr. Slaight and his radio broadcasting company Slaight Communications created the now venerable Toronto rock radio station Q-107 (CILQ). In 1985, he bought Standard Broadcasting, which would endure as the largest privately owned multimedia company in Canada until 2007.

As a boss he was known as a master delegator with limited patience. He wouldn’t read memos if they were more than a page long and would bang a gong at meetings if someone spoke for more than two minutes.

Small in stature, he imposed with a steely eyed stare, a tactical smile and an interrogator’s ability to say nothing. “In negotiations and at board meetings, he would just outwait everybody with pure silence until they caved in in a fit of uncomfortability,” Mr. Ben said.

Mr. Slaight’s most publicized deal was his part-ownership in the expansion Toronto Raptors in 1995.Randy Velocci/The Globe and Mail

Mr. Slaight hired capable people and gave them free rein. “People would walk through brick walls for him, because he gave them autonomy,” Mr. Ben said. “If you needed instruction, you were not the right person to work for him.”

Mr. Slaight had a lifelong obsession with magic, especially feats of mentalism, and wrote or edited several books on the Canadian magician Stewart James, his hero and mentor. His most prized possession was not his collection of radio stations, but his extensive library of magic books.

While he invented his own deceptions, he had no interest in explaining them. Ask him how an abracadabra of his worked, his answer was invariably, “Very well.” Once, when journalist Amanda Lang spoke with Mr. Slaight for The Globe at his home, she pestered him for his presto secrets as he led her toward the door upon completion of the interview.

“You have to tell me how you did it,” she begged. His answer, offered with a smile but with enough insistence to be taken seriously, ended the conversation: “Get out.”

He also abhorred command performances. Once at a dinner party, when asked for a show of magic, Mr. Slaight cut Alberta Premier Peter Lougheed’s tie in half, only to tell him “so sorry,” while feigning that he had forgotten the trick’s culmination.

Mr. Slaight made a fortune and gave away colossal portions of it. The Slaight Family Foundation and Slaight Music, now run by son Gary Slaight, support a variety of charities, with a special focus on health care and music-related endeavours.

He had a weakness for an ambitious lunchtime construction: peanut butter, fried egg, Kraft cheese, lettuce and mayonnaise on Wonder Bread. When it came to musical tastes, he was in favour of jazz, particularly Oscar Peterson, though he was also a friend of the troubadour Gordon Lightfoot.

Mr. Slaight had a lifelong obsession with magic, especially feats of mentalism, and wrote or edited several books on the Canadian magician Stewart James, his hero and mentor.Mike Blake/Reuters

His daily routine involved the scouring of multiple newspapers, crossword-puzzle solving and the ritual watching of Jeopardy! on television. Such was his fanaticism for the quiz show that for his 80th birthday his friends and family arranged for host Alex Trebek to tape a segment of the show (not for broadcast) with all the clues tailored for Mr. Slaight.

At his birthday party, when he went to watch Jeopardy!, a DVD of the special segment was played instead. All of the answers prompted the same question: Who was Allan Slaight?

John Allan Slaight was born July 19, 1931, in Galt., Ont., the first born son to newspaperman John Edgar and Eileen (née Wright) Slaight, a banker’s daughter.

By the age of eight, young Allan was performing tricks for classmates and employees of his grandfather’s bank, where a 15-minute set of magic earned him $2.

As boy he devoured books with “rags to riches” narratives, and while some might say he was born with a silver spoon in his mouth, he definitely acquired a gold front tooth when a schoolyard mishap knocked out the original.

Although his parents wanted him to attend university, at 17 Mr. Slaight instead began his career at CHAB radio in Moose Jaw. He worked as a news reporter, but also hosted a late night jazz program called Spins and Needles.

In 2013, Mr. Slaight, his second wife, Emmanuelle Gattuso, and the Slaight family gave a $50-million gift to the Princess Margaret Cancer Foundation.Handout

At 18, in 1959, he presented Woody Herman and his Woodchoppers at Saskatoon’s Club 400. When ticket sales moved slowly, Mr. Slaight used his Jottings on Jazz column in the Bop City Music Society of Saskatoon newsletter to shame readers into attending the show: “Jazz and Saskatchewan are comparable to cheap wine and a roller coaster ride. They won’t mix.”

At 19, he eloped with Ada Winifred Mitchell, moved to Edmonton, started a family, and jockeyed between local radio stations before becoming news director at CHED in 1953. He also performed as a touring magician-mentalist.

Arriving one afternoon in Clyde, Alta., Mr. Slaight was told to expect a full house because everybody in town wanted the mind-reader to solve a vexing civic concern. “You better be pretty good, sonny,” one wood-whittling old-timer told him, according to Slaight: Off Hand, a biography commissioned by the Slaight family. “Some son of a bitch has been poisoning our dogs, and everybody’s comin’ tonight to find out who done it.”

True enough, the community centre was packed that night. Toward the end of the show, Mr. Slaight declared that he knew the identity of the heinous individual. “It’s a man,” he said, making a safe assumption. “And he’s in the audience right now.”

Mr. Slaight went on to explain to the hushed crowd that a lack of hard evidence prevented him from making the perpetrator’s name public. He did say, however, that within weeks the pooch-poisoner would leave town. It was a bluff, but it worked. No more dogs died.

In 1958, he relocated to Toronto and became the program director of the upstart rock and roll radio station CHUM. Working with visionary promotion man Allen Farrell, Mr. Slaight lifted the money-losing station from third in the market to first by using zany contests, tightening the focus of the playlist and conjuring outrageous publicity.

All-night disc jockey Mr. Laine squeezed into a wet suit, strapped on scuba gear equipped with a special microphone and broadcast for three days underwater at the Sportsmen’s Show. Another DJ, Mike Darrow, became CHUM’s “guy in the sky” by living in a car suspended 60 feet in the air until 300 cars were sold from the lot of a local Chevrolet dealership.

The latter stunt epitomized Mr. Slaight’s mandate: “The primary purpose of CHUM on the air and functioning as a broadcasting station,” he wrote in a memo to the announcers, “is to sell the clients’ products.”

When Beatlemania hit North America in 1963, competing stations in Toronto battled over which one would be the city’s “Beatle station.” CHUM won that unofficial title through an affiliation with a group of Fab Four aficionados. “Sponsoring the Official Canadian Beatles fan club was a clever business move by CHUM, and as a result they left CKEY in their Beatles wake,” said Piers Hemmingsen, author of The Beatles in Canada.

In 1966, Mr. Slaight took his two sons to London, leaving his wife and daughter behind, to become involved with Radio Caroline, an unlicensed British radio station that broadcast offshore in international waters to circumvent BBC’s radio broadcasting monopoly.

He didn’t stick around though, pulling out of England in 1967 before commercial radio was introduced there. In 2005, he told The Globe that the timing of his departure was the biggest mistake in a career marked by little regret.

“I’ve had a pretty full and complete business and personal life,” he said. “I don’t look back and say, ‘I wish …’” Then he added with a laugh, “That’s probably because I’m an insensitive clod.”

In 1970, Mr. Slaight purchased Toronto radio station CFGM-1310 AM with the help of investment partners that included Mr. Lightfoot. The station would become Canada’s first full-time country and western music station. By 2007, his empire included 53 radio and two television stations, a package which he sold to Astral Media for $1.08-billion.

Mr. Slaight’s most publicized deal was his part-ownership in the expansion Toronto Raptors in 1995. Not long into the franchise’s existence, the Ontario Teachers Pension Plan led a buyout of Mr. Slaight from the team and Air Canada Centre (now Scotiabank Arena), giving him a nice return on his investment.

In 2013, Mr. Slaight, his second wife, Emmanuelle Gattuso, and the Slaight family gave a $50-million gift to the Princess Margaret Cancer Foundation. That same year, Mr. Slaight gave $18,000 to restore Fats Domino’s piano, which was damaged in Hurricane Katrina.

“He was a powerhouse and a pussycat,” said Julie Eng, executive director of Magicana, a Toronto-based organization dedicated to the exploration and advancement of magic.

In his 2005 interview with The Globe, Mr. Slaight waved off any connection between his passion for magic and his business acumen – “except, perhaps, the creativity required.”

Still, he couldn’t deny the appeal of the pizzazz, whether selling an illusion or peddling advertising. “The best magic trick in the world will fall flat,” he said, “if the presentation is dull.”

Mr. Slaight leaves his wife of 35 years, Ms. Gattuso; children, Gary, Greg and Marie; a brother, Brian; and grandchildren and great-grandchildren.

Editor’s note: An earlier version of this article said Mr. Slaight sold Standard Broadcasting to Astral Media for $1.2-billion. The selling price was, in fact, $1.08-billion. This version has been corrected.

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