These are troubling times for the MLSE esports giant given the turmoil at the Maple Leafs, Raptors and Toronto FC

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Brendan Shanahan is looking for a General Manager, possibly a Coach.

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Masai Ujiri is on the lookout for a head coach and a way to quickly reshape his squad.

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Bill Manning looks for the occasional win – and doesn’t find many.

These are not the best of times for the presidents at the helm of Maple Leaf Sports and Entertainment, owner of the largest sports conglomerate in this country’s history.

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The greatest teams under the MLSE umbrella have never been worth so much. But here they are, each in some difficulty, seeking leaders, victories, and a new sense of direction.

Years ago, Tim Leiweke smashed into Toronto like a hurricane, knocking over people and buildings, attacking complacency, pushing for Ujiri to be recruited from Denver, pushing for Shanahan to join the Maple Leafs from the NHL front office, pushing on money for it you have to blame it on the terrible football team who, while having loyal fans, didn’t have much to show for it.

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Leiweke invested, and the Leafs started winning, and the Raptors started winning, and Toronto FC won an MLS championship (and probably should have won three). And when Larry Tanenbaum and others at MLSE couldn’t get along with Leiweke – he’s a handful and more – they mutually agreed to part ways.

But a culture was built of winning — and using financial power to win and achieve what others couldn’t.

Shanahan has had a pretty remarkable nine-year tenure as Leafs president, despite what didn’t happen in the playoffs. When he first took the job, he knew one thing: this is the Maple Leafs, they deserve the best.

So when he needed a coach, he overpaid for Mike Babcock, who won two Olympic gold medals and a Stanley Cup victory in Detroit. And when he needed a general manager, he recruited his former mentor, Lou Lamoriello, who was already in the Hockey Hall of Fame, and brought him to Toronto. In between, he explored all of junior hockey and identified three people he wanted to hire: Kyle Dubas, Mark Hunter, and Kelly McCrimmon.

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He got two of them.

Dubas became his general manager. McCrimmon became general manager in Vegas. Following Dubas’ appointment, Hunter returned to London, Ontario as general manager.

Now Shanahan is under pressure. He ousted Dubas. His special assistant, Jason Spezza, chose to accompany him. The Leafs’ front office is thinner than it has been since Shahanan’s arrival. The new general manager may need a coach – it’s up to him to decide – who needs new staff. That’s a lot of movement for a team with the fifth-best record in the NHL this season, which faces big decisions about the futures of Auston Matthews and William Nylander.

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Is there a Lamoriello out there? The Edmonton Oilers went in that direction, hiring Ken Holland, who had slightly more success than Dubas in his stable with Connor McDavid and Leon Draisaitl. Are there any other legendary general managers in the NHL right now? Most of them are faceless former players like Don Sweeney or Jim Nill. Some are former stars like Steve Yzerman or Ron Francis or Rob Blake or Joe Sakic. Two-thirds of NHL GMs played professional hockey. But some of the best — Julien BriseBois in Tampa, McCrimmon, Doug Armstrong — didn’t.

The challenge for Shanahan now is to stick to his original plan: How do you find the best when you’re short on time and the stakes are so high? Arguably the best GM in the NHL today is Boston’s Don Sweeney.

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Gone are the days when the NHL was occupied by power players like Harry Sinden, Glen Sather, Cliff Fletcher and Bill Torrey. You can’t go and steal a Fletcher like the Leafs did in 1991. Or maybe yes.

Ujiri must find a way to replace Nick Nurse who played a pivotal role in that fabulous 2019 championship run. Ujiri was also a tremendous effort in that win. He traded for Kawhi Leonard when that seemed impossible. He swapped for Marc Gasol on the deadline. If he doesn’t take those two steps, there’s no run and no cheering. And if he doesn’t hire a nurse, the same applies.

Now he has a mediocre NBA roster at a time when the Miami Heat are likely to be playing for the championship. The Heat have won 44 games this season. The Raptors have won 41. One team seems close, the other so far away. But this has got to be the summer of Ujiri: hire the right coach, make the right deals, and make the Raptors meaningful again.

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Toronto FC is still a long way from that. This is Manning’s biggest mess. He is the president of the CFL’s football team and Argonauts. The Argos have clinched an unlikely Gray Cup win in a city that only seems to shrug at the accomplishments of its oldest franchise. The problems of the Argos are almost insoluble. But TFC is about a product that is borderline terrible.

What’s even more discouraging about TFC is that they have the second-worst record in MLS while also spending the most on payroll. Cincinnati has the best record in the east. It pays its players $12 million. Runner-up Nashville spends $5 million. TFC tops the league with a salary of $26 million.

It all adds up to two wins this season, not a single away, and the 28th-best record in a 29-player league.

The 2017 TFC Championship and the 2019 Raptors title seem so long ago. It’s not as long ago as the Leafs’ last Stanley Cup, but that’s always another story.

MLSE, with all its money and power, faces challenging days for its team presidents.

Big decisions await. Uncertainty is the norm today.

ssimmons@postmedia.com

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