After a couple of days of pointedly time-sensitive denials, the news that Tim Leiweke is leaving as president and CEO of Maple Leaf Sports and Entertainment within the next 10 months is more than a management shuffle. It’s a decapitation.
The body he leaves behind will continue twitching for a while. Maybe a season or two. But, eventually, it’s going to die.
Mr. Leiweke was more than a manager. MLSE has had a whole bunch of those.
He was a visionary, an 18-hour-a-day dynamo, a man who could work himself near tears thinking about the possibilities (and often did).
He brought in or elevated a series of fellow travellers who now control all aspects of the corporation. In every case, in every conversation, every one of them was keen to tell you who lit the fire underneath them: Tim.
“He is the most incredible person I’ve ever met,” an MLSE exec once told me, with a religious sense of awe.
For the past year, MLSE has been run as a function of one man’s outsized personality. It can’t just go back to being an insurance company that happens to own a hockey team.
Troublingly, they also can’t find another guy who exists at Mr. Leiweke’s level, because such a person does not exist. He wasn’t just the best-connected sports executive in the country. He may have been the most hooked-in entertainment operator in the world.
Take the most famous Leiweke recruit – Drake.
In recent years, the hip-hop star had reached out on several occasions to MLSE, wanting to get involved with the Raptors. He didn’t really care how. This wasn’t a business opportunity. This was a fan with leverage.
No one at MLSE ever returned his calls. Think about that. Seriously. If you’re a fan of any one of MLSE’s teams, have a long think about what you’re going back to.
Eventually, Drake gave up.
Shortly after taking the job in Toronto, Mr. Leiweke was back in L.A. having a friendly chat with Scooter Braun, the man who manages Justin Bieber’s musical career. Mr. Braun mentioned Drake’s interest. Mr. Leiweke made the call.
Drake had no suggestions as to his role. Mr. Leiweke dreamed up the global brand ambassador title. It was all done in days. The effect on the club’s continental reputation has been seismic.
Draw a straight line from Drake to the “We The North” campaign to Kyle Lowry deciding he preferred the Raptors to the Lakers or the Knicks. Draw a line between all those moves and relevance.
Two years ago, that was impossible. Two years from now, without Mr. Leiweke, it’s impossible again.
Mr. Leiweke brought two things that cannot be pulled from the air by a new CEO, regardless of how competent – connections and a single-minded drive to put his personal stamp on every part of a business.
The thing that should give the next man or woman in charge pause is how deeply every important player in this organization is beholden to the last guy.
Without Mr. Leiweke, Masai Ujiri is not the general manager of the Raptors.
Without Mr. Leiweke, Jermain Defoe and Michael Bradley don’t both make risky leaps to Major League Soccer. It was Mr. Bradley’s agent, Ron Waxman, who reached out in the first place to Toronto FC. He’s the one who sold the idea to his player. Why?
“I really liked what Tim was doing there,” Mr. Waxman said. Not the team. Not the GM. “Tim.”
It was Mr. Leiweke who strong-armed MLS into allowing the move to happen. Because he knows everyone at the league. He knows everyone at every league.
Without Mr. Leiweke, Brendan Shanahan does not become the president of the Maple Leafs. Again, it was Mr. Leiweke who smoothed the idea of poaching one of the NHL’s comers by going to another one of his old pals, Gary Bettman.
Notably, Mr. Leiweke did not bring a single employee with him from AEG. He won over most of the existing staff. The ones who didn’t want to be won over, he replaced. The joint is not full of his loyalists. It’s got nothing but.
In replacing him, MLSE has three problems: the past, the present and the future.
The past suggests that this corporation is not a friendly place to spend your peak professional years. In announcing his departure a year after his arrival, Mr. Leiweke hasn’t helped much on that score.
The present is built on a foundation entirely of his creation. Every one of his hires has plenty of other options.
Mr. Ujiri, for one, has been frustrated at the corporation’s initial reluctance to build his team a new $30-million training facility (a key recruiting tool). It’s only happening now because Mr. Leiweke went to war for him at the board level.
What’s keeping Mr. Ujiri here now, aside from a paycheque? Who is his rabbi in management?
The same could be said of Mr. Shanahan. Or Mr. Bradley. Or a bunch of other behind-the-scenes people who’ve been instrumental in this Great Leap Forward.
However, the real issue is the future.
Just a few days ago, we were talking in this space about Oklahoma City Thunder star Kevin Durant, and the possibility that he might choose Toronto in two years’ time. That was always a reach. Without Mr. Leiweke, it’s hopeless. He held that plan together. He knew all the players involved. You can’t hire another person who can do that. There isn’t one.
Before Mr. Leiweke, MLSE worked like a bank. It had money. It offered money to people it wanted, and hoped they’d come. Few did. That mentality is useless when all three of your teams operate in a salary-cap environment.
These days, every ascendant organization rides on one of two things – its history or its personality. No Toronto team has a recent history it wants to talk about.
So all they have to sell the stars of the future and build these clubs into winners is their personality. And it just quit.