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Keith Pelley, president of Rogers Media

This used to be date night for Keith Pelley and his wife.

Seventeen years ago, the then-newlyweds designated Tuesday evenings as sacrosanct. It served them well, maybe even saved their marriage, especially in its early days when Mr. Pelley was a frenzied hockey and football producer for Fox Sports, based in New York.

"I was travelling 230, 250 games a year," he explains, sipping a half pint of amber dry in a rambling, family-style Italian restaurant out on The Queensway in Toronto's west end. "Then I'd go over to Europe for three, four months to do NFL Europe. I was never home.

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"When we got married, I would say maybe 50 per cent of the people at our wedding would have given us a chance, to be honest with you."

A little while ago, though, date night got moved to Thursday. Which is how it came to be that, on this summery Tuesday in June, Mr. Pelley, the president of Rogers Media, finds himself talking about business in a place where he usually goes to escape all of that.

Mamma Martino's is his regular haunt: He and his wife Joan are here so often, they simply call it "the restaurant." (In fact, one Valentine's Day, it's where he proposed to her.) But he's a born showman, too, with more than 30 years of experience in television production, and he knows how to sell. Over a two-hour dinner, like an eager talk show guest he reels off a series of anecdotes, beginning each one: "Oh, this is a good story."

So, never mind that Mr. Pelley's compensation in 2013, according to a Rogers proxy circular, was a sniff more than $1.8-million. Ignore the shirt cuffs with their monogrammed "KWP." (Walter is his father's name.) Forget it was he who oversaw Rogers's astonishing 12-year, $5.2-billion purchase of the NHL broadcast rights last winter, a deal that has plenty of Canadian hockey fans worried they'll have to pay to see games that used to be free. The folks at this straight-up Etobicoke restaurant are his constituency. He kibitzes with the owner, Bruno, and compliments Bruno's waitress, Jane, on her dress.

Mamma's pastas, pizzas and veal marsala go for less than $10 each, statuary and fountains are out front, clusters of fake grapes and old family photos adorn the exposed brick walls, and there's even a picture of the Mona Lisa for good measure. Parents bring their kids here for dinner, then everyone saunters over to Tom's Dairy Freeze next door for a cone or a banana split and watches the sun melt slowly in the distance.

But if Mr. Pelley is here to escape, his business finds him, anyway: In the other room, a TV tuned to Sportsnet is showing the Toronto Blue Jays; Rogers Media owns both the channel and the team. Under Mr. Pelley's leadership since September, 2010, the high-profile division of Rogers Communications owns more than 20 conventional and specialty channels (including the City network, Omni, F/X and seven Sportsnet TV services), more than 50 radio stations, and dozens of consumer and business publications as well as the all-you-can-read digital magazine service Next Issue Canada.

When he took over the helm from the Rogers lifer Tony Viner, Mr. Pelley told associates he intended to make the company No. 1. "Yeah, I'd say I'm competitive," he says, his head low over the table now; he is practically whispering. "Oh yeah."

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The drive to be No. l has been bumpy. Sportsnet has been on a tear, and will benefit enormously from the NHL games. Still, in the past two years, Rogers has launched City stations in both Montreal and Saskatchewan. But it doesn't have a full national footprint, leaving the network a persistent also-ran behind Shaw Communications Inc.'s Global Television and Bell Inc.'s CTV Network. (Bell owns 15 per cent of The Globe and Mail.)

In an appearance before the Canadian Radio-television and Telecommunications Commission during the spring, Mr. Pelley said the conventional television industry's well-chronicled troubles were intensifying: He noted that Rogers had lost $38-million on City in 2012 and $42-million in 2013, and that he couldn't even trust the sales projections his executives had made five months earlier.

"Where's it going?" he asks, now rhetorically. "Isn't it changing like – " he snaps his fingers – "changing at a torrid pace?"

So how, he is asked, can he make a five-year plan with any legitimacy?

"The only thing you know about that five-year plan? That it's wrong," he chuckles. His voice jumps an octave, as it tends to do when he is excited. "It's the only thing you know! It's the only thing!"

We pause to order dinner from Jane. He requests the meat ravioli and another half pint of amber dry. But when the complimentary garlic bread arrives and neither of us wants it, he tries to give it back and is disappointed to learn that health codes prevent it from being given to someone else after it has touched our table. "Well, now, that drives me crazy," he says. "So much food is wasted. That's an interesting lesson. Next time, I'm gonna say, 'Don't bring the bread.' See? You learn something every day."

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Then, back to business: "I think over the next five years, we'll be the dominant player in the media and the content space." Hockey is the linchpin. Mr. Pelley won't give away many clues about what's to come – he won't confirm or deny the possibility of equipping players' helmets with cameras – but says the 12-year deal makes Rogers and the NHL true partners, because neither is just positioning for the next contract.

One thing is for sure: Rogers will use all of the media platforms at its disposal to build the game. "Today's Parent will be involved," he says. "Chatelaine. Cityline." So, maybe P.K. Subban's favourite fall recipes? "Yeah, that kind of concept," he nods. "There'll be far more emphasis on the stars of the game than on the business stories."

The industry was very different when Mr. Pelley first got into the business as a student in the radio-television arts stream at what was then known as Ryerson Polytechnical Institute. Still, it took commitment. He spent one summer working days at Ronald H. Chisholm Ltd., a food importer-exporter where his father was a vice-president, then clocked in for a nightly 6:30 p.m. to 2:30 a.m. shift as an editorial assistant at TSN.

"It was $35 a shift, but I couldn't say no to getting into the business." His boss was Scott Moore, who now works for him as Rogers's president of Sportsnet and NHL Properties.

After graduating from Ryerson, Mr. Pelley landed a producer gig at TSN. He bought a townhouse near the studios, where a number of the people he is working with now – including Mr. Moore and Dave Randorf, whom he just hired away from TSN for the Rogers hockey broadcasts – were roommates. "Joel Darling, he worked at Hockey Night in Canada as an associate producer, he would bring home the Stanley Cup."

Wait, I ask: Doesn't the Cup travel exclusively with that guy in the white gloves? "Nah. Joel brought it home in a big tuba case, and we'd all get in the bathtub and take pictures with it." He adds quickly: "With our clothes on." Then he smiles at the memory and forks into his ravioli.

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Within a decade or so, Mr. Pelley was heading up programming at the CTV-owned sports channel. A few years later, he was named its president. In 2003, he left to become president of the Toronto Argonauts, helping stabilize the CFL club after a tumultuous period.

"It was pretty hands on," he says, chuckling wryly again.

"I'd speak at the opening of a letter, if I thought I could sell a couple of tickets."

Four years later, he was lured back by his old bosses at CTV to head up the Olympic Broadcast consortium for the Vancouver 2010 Games, overseeing an unprecedented effort that brought together the TV and radio properties of Bell Media and rival Rogers. In the run-up to the Games, he tub-thumped relentlessly to convince his normally restrained countrymen to unleash their patriotism.

"The Americans celebrate their stars, they celebrate their heroes. I think Canadians need to be a little bit more nationalistic. We were that in Vancouver," he says. "It became a rallying cry for a nation."

It also became a nice notch in Mr. Pelley's CV, one that proved he could manage a gargantuan operation. A few months after the Games wrapped up, Rogers came calling.

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As president of Rogers Media, he is now doing battle with some of his closest former colleagues. "It's just business," he says, and though he shrugs, he has a glint in his eye. He looks down, grabs the garlic bread, and sops up the extra sauce on his plate. "It's very good." He orders another half pint of amber dry.

Joan calls, and he tells her he'll be home soon. After he hangs up, he says he works very hard to carve out time for his wife and two children, Jason, 11, and Hope, 7. It's not easy. "I could work all the time. I love it," he says. Still: "At Jason's graduation, at Hope's graduation, and their marriages, at their weddings, it's very important to me that I've been a significant part of their life, and Joan hasn't raised them [alone]."

Family is why he came back from the U.S., to be near his parents. Almost five years ago, as a perk for organizing the Olympic torch relay, he got to be one of the 12,000 torchbearers. In a nod to his father's Newfoundland origins, he chose to run in Corner Brook. His dad had left there decades ago, arrived in Toronto "on the back of a pickup truck, and worked his way up."

His mom and dad were there with him last January to celebrate his 50th birthday, when Mr. Pelley's friends David Cynamon and Howard Sokolowski – the owners of the Argos when he was president – rented the Mod Club in Toronto's Little Italy. "It was really neat."

"They threw a great party, and then they brought out Burton Cummings. And at 12:30, he came out for the third time, and I sang Takin' Care of Business with him. Oh, it was cool."

Was he friends with Burton Cummings? "I'd never met him before in my life!" he says. "But I love B.C. Love him."

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Born

Jan. 11, 1964, Toronto

Family

Married 18 years to Joan Pelley

Two children: Jason, 11, and Hope, 7

Two dogs: Taffy and Bella

Education

Radio and television arts degree, Ryerson Polytechnical Institute

Diploma in speech and drama, Trinity College, London

Career highlights

President, Rogers Media (as of Sept., 2010)

President, Canada's Olympic Broadcast Media Consortium

President and CEO, Toronto Argonauts Football Club

President, TSN

NFL and NHL producer, Fox Broadcasting Company

A rocky beginning

In high school, Mr. Pelley and a buddy started a DJ company called 4D Sound.

"I've been to more weddings than you will ever be at in your life!"

Their motto: "Music that takes you one dimension beyond."

He recalls: "We started on albums, moved to tapes, and ended on CDs. But in the early days, I did one wedding – this was an hour and a half, two hours away, and the first song was Sharing the Night Together. So we get to the sound check, and I go: 'Dr. Hook, do you have it?' 'I didn't get it. I said you were to get it.' 'Well, I didn't get it!' Think of that concept now; you can download everything! Back then? You've got to go meet the bride, and say you don't have the first song."

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