Opinion: Maple Leafs Parting with Kyle Dubas Rings Alarm Bells

It’s been a few days since the Friday afternoon press conference by Brenden Shanahan that seemed to plunge the Toronto Maple Leafs into chaos. 

In Shanahan’s nine-year tenure, he’s mended fences with key alumni such as Dave Keon, restored order to one of hockey’s most recognizable brands and instilled confidence in a fan base that was starved for normalcy. He was brought in by Tim Leiweke, who also brought on Masai Ujiri and Bill Manning – both have won league championships in Toronto.

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Leiweke’s stay was short, but it was impactful. With three hires, he turned around three major league franchises. MLSE has not been the same since his departure, and that has never been clearer. Toronto FC, a club considered to be one of MLSE’s leading brands, has plunged into despair. Bill Manning remains, but there are questions of how much longer he will hold the seat. The Toronto Maple Leafs were chugging along just fine until Friday afternoon when the ghosts of Harold Ballard and the Pension Plan seemed to re-enter the halls of 50 Bay St.

When Canada’s largest telecoms purchased a large majority of MLSE, Larry Tanenbaum remained the face of the company. When Leiweke took over from Richard Peddie as the CEO, he convinced two companies who can never agree on anything to agree on his vision for the company. A decade later, it seems he not only convinced them of his vision but that he was a strong enough voice to shield his team presidents from board involvement.

I worked at MLSE under Leiweke and remain very close with a few people who remain at MLSE. Leiweke leaving set off a chain of events that likely led to Friday’s debacle. MLSE had a culture under Peddie and Leiweke, and many have felt that Michael Friisdahl’s appointment as the CEO was the decision of the telecoms. Regardless of successful teams and profits, sources said the turnover rate and unhappiness have reportedly increased. They also said many company programs were cut, learning opportunities and culture builders that were key under Peddie and Leiweke reportedly disappeared. The board became far more involved in team-level decision-making with the Leafs, Raptors and Toronto FC. One wonders if that was the reason Tanenbaum intervened to save the company from losing Ujiri a few years ago.

Friisdahl left in 2022, and MLSE has not had a permanent CEO since, just an interim CEO. A multi-billion-dollar corporation without a CEO. Without a CEO, team presidents were dealing directly with the board. Instead of the shield Peddie and Leiweke provided, teams have been forced to deal with the demands of ownership. If you know anything about Bell and Rogers, you know a few things: they never agree on anything, and share price is king. Cutting company incentives was the first sign of what was to come under this ownership umbrella without a sport-centric CEO like Leiweke at the helm. With due respect to Friisdahl, he was an Air Canada executive, and shielding teams from ownership involvement is not something you’re prepared for unless you’re familiar with it.

I do not believe for a moment that Friisdahl’s departure coincided with reports of increased involvement from MLSE ownership over the last year. Tanenbaum is always around, in the dressing room and in his seats. He’s affectionately known as Uncle Larry at MLSE, which is to say, he’s well-liked. Most people at MLSE have no idea who the Bell and Rogers executives are, but they can tell you when they’re in the building. When you have empty C-level offices and ghost executives who are reportedly influencing decisions, that can cause problems.

That brings us to this past week. An emotional Kyle Dubas laid bare the impact this season had on him and his young family. It was a rare moment of vulnerability for an executive in a sport that sees any sign of emotion as mental weakness. A franchise lauded for how it treats players showed an executive the door days after he showed vulnerability. Regardless of what happened in between, the optics of that are horrendous.

Shanahan handled the press conference like Real Madrid president Florentino Perez or Bayern Munich CEO Oliver Kahn. That is, he was transparent with the fan base, forthright with the process and clearly, unhappy with how things played out. It took many by surprise because NHL executives aren’t known to peel back the curtain in that manner. However, that level of transparency has been required by supporters in European football for years. Frankly, it should be demanded in hockey given all the skeletons that have been unearthed the past few years. You didn’t have to like what Shanahan said or did to Dubas, but that level of transparency is the norm for all of sport’s global giants. If the Leafs want to be treated as a global sporting giant, they need to act like one.

Whether it is Real Madrid, the New England Patriots or New York Yankees, there is a certain decorum required to be a top sporting club. One of those requirements is to have a CEO who can not only manage the company but can manage the owners. Half the job of C-level executives and presidents of sporting clubs is managing upward. I’d wager that more than half of NHL GMs have more conversations with their ownership group than with other GMs. Having a buffer is important, especially when we’re discussing one of the most valuable NHL teams.

There was supposed to be one between Shanahan and the board and without it, it seems that the buffer between the board and Dubas went away, too. Multiple reports have suggested that the MLSE executive board was far more involved than in the past. Corporate executives who spend their time on share prices needn’t be making decisions on who is traded or signed. Major decisions such as contract extensions require approval from the board, but at no point should an owner be vetoing trades or dictating day-to-day hockey operations. Not in a successful franchise, anyways. Unless your name is Michael Jordan or David Beckham, two owners in their respective sports, the odds that the owners know what trade is best are next to zero. We’ve seen time and time again that meddling ownership is a team’s biggest roadblock to success.

If the reports of Dubas having decision-making power lessened are true, and I have no reason to believe they aren’t, that should raise alarm bells. I say this because it mirrors the current landscape at Toronto FC in that ownership has become more involved in decision-making there as well. The MLSE board and Shanahan had reason to have reservations when Dubas’ agent came back with a significantly different financial package. Anyone would. If that was the reason the parties decided to go their separate ways, MLSE has lost a bright young executive, and Dubas should fire his agent. However, if the crux of the issue was that Dubas wanted control of hockey operations, the department he oversaw, he should have been afforded that. Not a single Leafs fan would say they’d prefer the telecom executive making hockey decisions over Dubas and they’d be correct.

Something Leiweke said when I worked at MLSE has stuck with me years later: “If you’re going to get rid of someone, you better have someone better in mind.” I’ve seen quite a few names in the rumor mill, and I’m not sure any of them are better than Dubas. From a hockey standpoint, there will be arguments. 

From a human standpoint, Kyle Dubas led a forward-thinking, positive culture. It is rare in hockey that not a single person within an organization has a bad thing to say about someone. When Jason Spezza resigns and Auston Matthews is no longer sure about signing an extension, it speaks to how well-respected Dubas is. He’s earned that loyalty.

If the decision to show Dubas the door ends with Matthews following, the blame should lie squarely with MLSE’s board, who will have cost themselves millions of dollars by allowing the most talented player in franchise history to walk because they wouldn’t allow his boss to make the decisions he was hired to make. One thing is for sure, the money MLSE will cost themselves if Matthews leaves is far greater than the money Dubas asked for. No doubt about that. In the end, last week may go down as the one that plunged the Toronto Maple Leafs back into chaos over what seems to be a couple million bucks and boardroom drama. That seems quite ridiculous when the ownership group is worth nearly 100 billion dollars, but I guess this is what real-life Succession is.