No. 172: KEITH PELLEY / Chief executives in sports style themselves as corporate sharks. Like the real-life ocean predators, they know if they stop moving they will die. Career-wise, anyways.

Maple Leaf Sports & Entertainment recruited an exec they knew & one familiar to many in Toronto. Don't mistake it for a lifetime appointment. Or even a long-term one. The nomads in the corner offices.

An older, flattering picture of Keith Pelley from a Golf Digest profile, circa his hiring by the European Tour. Don’t be surprised if MLSE strikes a deal with Warby Parker.

THE BUSINESS OF PROFESSIONAL SPORTS is clubby and if you labelled it a boys’ club you’re within your rights. If you want to sprinkle the description with terms like “middle-aged” or “white privilege” or whatever, ditto. It ain’t exactly the school-tie signal-sending system of old, but it’s not that far removed.

It’s also a business of turn-over at the executive level. Based on no data, just impressions, business that thrive in other realms have generational turn-over and often the reins are turned over from matriarch or patriarch to kinder, which is to say there’s no real turn-over at all. Pro sports isn’t, say, radio, where the only real fixtures are the mics and mixing boards and the decision-makers’ job security is only as good as the last set of ratings. But if things go bad, owners of sports franchises seem disinclined to ask execs in charge of operations to change course; their usual course of action is to open the trap doors or hit the button on the ejector seats and then interview candidates, the more familiar their names and mote extensive their track record the better.

A few enter the circle and just when you become accustomed to them in certain roles, the savviest suddenly announce they’re heading off to a new job—they know that nothing is a lifetime appointment and it’s best to get out ahead in the process. They know when there are storm clouds ahead. They don’t need a weatherman to know which way the wind is blowing. There are the survivors and then there are thrivers.

Okay, enough of the didactic.

Keith Pelley is a thriver. Pelley, 60, is stepping out of his role as head of golf’s European Tour and assuming the presidency of Maple Leaf Sports and Entertainment. (His tenure heading up the European Tour is playing to mostly but not entirely positive reviews, per this Golf Digest feature last week, linked here: “How do you assess Keith Pelley’s legacy with the DP World Tour? It’s complicated—and unfinished.”)

Among those that know him, that he’d one day be a CEO of MLSE would have been somewhere between a possibility and foregone conclusion. In Toronto he has been a name in media circles for three decades and his start at TSN goes back farther than that. A mover-and-shaker. (He should be thankful that Bob McCown’s nickname for him never caught on: “Thing 1,” cribbed from The Cat in the Hat.)

In the flesh, I’ve only spoken to Pelley a couple of times. When I was at Rogers Sportsnet, he occupied the corner office on a floor that I didn’t have access to, but at company events I’d bump into him. He’d usually be situated in the middle of a crowd of wannabes and suck-ups and even casual readers of this SubStack know that ain’t me in the remotest. Don’t have the careerist gene.

I doubt Pelley even knew me to see me. I suspect he did know my name—a fading memory maybe—because I wrote a profile of him. Yeah, we know a lot of the same people and some of them are even my friends. And there was some overlap in our time at the school that’s now called Toronto Metropolitan University. But really, though, he’d know my name from the profile I wrote of him for the National Post Business Magazine in 2008—you’ll find my uncorrected first draft below the paywall at the foot of this story.

Pelley in 2012, in honeymoon days as CEO of Rogers Media, being honoured by ye olde alma mater. His term at Sportsnet would, like the name of the school, be a matter for reassessment.

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I drew the assignment when Pelley resigned from the presidency of the Toronto Argonauts to head up the Canadian media consortium that was ramping up for the 2010 Olympics in Vancouver. That consortium paired Bell and Rogers, previously rivals, adversaries or blood enemies. What had previously been a competitive business environment was going to be a collaborative one and he had to ensure that the kids shared the toys, as it were. If you’re trying to connect the dots, yes, the two major consortium members are in their own unlikely partnership these days, as MLSE’s proprietors. Coincidence? I think not. If he could bring peace to the playground the first time in the short run, he might be able to do it again.

Pelley knows the business cultures at Bell and Rogers. As I would lay out in the mag profile, he broke into the business at TSN, which has long been Bell’s crown sporting jewel. And as I put together from the social notes about company parties, Pelley worked at Rogers with Sportsnet—he came in at One Mount Pleasant as the rainmaker shortly after the consortium’s successes in Vancouver made him the most desired free agent in the business.

Back to 2008: I had real hopes for the piece. Certainly it was timely and it was also an opportunity to go behind the scenes. Everyone sees what’s on the screen, but not much at all on the other side of the cameras. And I thought that someone managing a hydra-headed media monster would value a profile in a mag that would be read by many folks in the business sector, those who’d actually be looking at investing advertising budgets and coming along for a ride with the consortium.

And there were personality and history. Pelley occasionally dropping in on Bob McCown’s Prime Time Sports. I even sat across from him on the TSN show. As I’d note in the final piece.

MAYBE YOU’VE SEEN Keith Pelley on TSN¹s “Off the Record.” If you haven’t, take it from someone who has sat across from him: Three other panelists and the host are instantly transformed from contributors to a dialogue to an audience for a monologue. He has all the answers to every question and would run laps around the set if they let him.

Sigh. One piece of advice I can offer sportswriters and writers outside the sandbox: Media types can be difficult to deal with. And they don’t mind big-footing you. Many, not necessarily the best, enjoy big-footing you.

Given the hectic schedule and pressing matters, Keith Pelley didn’t have a crazy amount of time to spare me, something he emphasized when he scheduled and cancelled a couple of meetings with me. I started to wonder if I was going to have to go into the full “Frank Sinatra Has a Cold” mode a la Gay Talese (the full classic linked here).

I’ve written before about the “write-around,” the composition of a profile without the profile’s subject’s participation and often at the subject’s objections. In No. 109: MICHAEL JORDAN & WILLIAM BEDFORD / The write-around in Chicago, Part II I recount how getting stiffed by MJ landed me in the office of the coach of Marshall High’s Commandoes, the inner-city team in “Hoop Dreams.” In No. 121: MAX DOMI & FATHER / Fit to be untied, I walk through how the infamous Tie helped me arrange time with his son … so long as Tie wasn’t quoted or his name even mentioned.

While I waited for a private audience with Pelley, I had a few useless interviews with Pelley’s colleagues, co-workers and friends. I talked to Scott Moore, another grad of Ryerson who went from the radio-and-television program to TSN in its early days. Moore did the James Brown—talked about, said nothing. Brian Williams, the longtime master of Olympic ceremonies for CBC, was the same story—I kept waiting for him to say something like, “It’s 4 p.m. here in Torino.” I didn’t bother including either in my final story and more than a half dozen other familiar names in sports-media fell into that category. There’s only so much room for the formula platitudes, “great guy,” “ridiculously talented,” et cetera.

When I finally got my time with Pelley, well, he kept looking at his watch. He was determined to do the bare minimum. He was always fine to do broadcast like McCown or Landsberg’s shows, where get he could get his message out without filtering, laughs and elbows in the ribs and all. A magazine piece? He was too used to be a director and producer to take pointed questions from anyone who wasn’t signing his paycheques. There’s a difference between real talk and talk-show banter.

Pelley landing with MLSE has prompted speculation. Will he be the one to apply pressure to Brendan in the hockey department and Masai with the Raptors? Is he going to spearhead a bid by MLSE to acquire a franchise in the Premiership? I wouldn’t race out to bet on the Leafs finally get a championship under his stewardship, not on the Raps doing likewise. Go back to his gig after the Olympics, when he signed on with Rogers—his successful push to acquire NHL rights for Sportsnet at the cost of $5-billion never came close to going according to plan. Of course, by the time that was plain to all, he was out of the building faster than Elvis and packed his bag for the golf job.

Even if Pelley were wildly successful, he’ll almost certainly be on the move again soon enough. As I said at the outset, there are no lifetime appointments—that’s the nature of the business.

A lot of people thought MLSE won the executive lottery when they landed Tim Leiweke, another rainmaker, back in the spring of 2013. Leiweke had a rep from his time with the outfit that had the Kings and Galaxy and a piece of the. Lakers in L.A. and he did bring in Shanahan to run the Leafs and Ujiri to do likewise with the Raptors. Yeah, I too remember his promise of the Leafs winning the Stanley Cup (the CBC.ca story linked here). For those who can’t hit the link because of laughter, here’s the money quote.

But 18 months after the vaunted hire, Leiweke announced he was going to be on the move again, back out west, this time with the outfit that was bringing the NHL into Seattle and doubtless he was neither taking a cut in pay nor opting for a scrappy start-up.

Without further ado, here’s the Pelley profile from back in the day. Thanks for reading.

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From the National Post Business Magazine:

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IT was nothing planned. It just sort of happened. One of the people at the table in Hy¹s Steakhouse boasted that he could identify a California Cabernet with just a drop on his palate. Keith Pelley made it happen. He flagged the waiter and ordered an array of wines. They were brought out so that only the waiter knew the American from the French. In Vancouver, the Games of the XXI Winter Olympiad were underway.

Okay, so wine-tasting isn’t really an Olympic event, and it was January 2008, about 750 days away from opening ceremonies. No matter, Keith Pelley was thinking Olympics -- just what you¹d expect of the freshly appointed president of the CTV-globemedia-Rogers Communications consortium that will broadcast the Winter Games from Vancouver and Whistler. The others at the table were on Pelley’s bandwith, including Alon Marcovici, president of the consortium’s digital and research division, and members of his ever-expanding staff. This meeting was a get-acquainted session, the wine-tasting an impromptu, interactive component.

When Pelley was recruited for this job last year, he knew where his learning curve would be steepest: Online. That’s what had changed most since he went from the presidency of TSN, Canada’s No. 1 sports network, to be president and CEO of the CFL’s Toronto Argonauts in 2004. Then again, everyone was learning, because the digital world was, is and will be changing right through the Games -- whether it’s the technology, the public’s ability to access it, or corporation’s success at profiting from it.

For the group at the table, this potential was heady stuff. “Vancouver will be the first digital Olympics,” Marcovici declared. “By 2010 the digital natives, the Gen Yers, will out-number the digital immigrants, the Baby Boomers.” Pelley, too old to be a native, recognized the challenge: A television broadcast of a sports event is like wine-tasting; whether it’s going from one camera to another or sorting out Cabernets, it’s making educated guesses, drawing on history; digitizing the Olympics, having Canadians watch it on 12-inch and 2-inch screens, was going to require a vision of the future. “These Olympics will make history and so will we,” he told them. “We’ll set the standards for every Olympics to come.”