SIMMONS: Troubling times for the giant that is MLSE

Brendan Shanahan is looking for a general manager, possibly a coach.

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Masai Ujiri is looking for a head coach and a way to quickly shake up his roster.

Bill Manning is looking for the occasional win — and isn’t finding many.

These are not the best of times for the presidents who occupy top billing with Maple Leaf Sports and Entertainment, owner of the largest sporting business conglomerate in the history of this country.

The biggest teams under the umbrella of MLSE have never been worth more. Yet here they are, each in some difficulty, searching to find leaders and victories and a new sense of direction.

Years ago, Tim Leiweke burst into Toronto like a hurricane, knocking over people and buildings, attacking complacency, pushing for Ujiri to be hired out of Denver, pushing for Shanahan to arrive with the Maple Leafs from the NHL front office, pushing for money to be thrown at the terrible soccer team that had dedicated fans, but not much to show for them.

Leiweke spent 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 deal with Leiweke anymore — he is a handful and then some — they mutually agreed to part ways from each other.

But a culture was built around winning — and utilizing financial power to win and accomplish what others could not.

Shanahan has had a rather remarkable nine-year run as president of the Leafs, all that in spite of what hasn’t happened in the playoffs. When he first took over the job, he was clear about one thing: These are the Maple Leafs, they deserve the best.

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

He got two of them.

Dubas became his general manager. McCrimmon became general manager in Vegas. Hunter, after the Dubas appointment, returned to London, Ont., as general manager.

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Now Shanahan is under the gun. He pushed Dubas out. His special assistant, Jason Spezza, chose to walk with him. The Leafs’ front office is thinner than it has been since the time Shanahan arrived. The new general manager may need a coach — his call, I suppose — who will need a new staff. That’s a lot of movement for a team with the fifth-best record in the NHL this season and facing huge decisions about the futures of Auston Matthews and William Nylander.

Is there a Lamoriello out there? The Edmonton Oilers went in that direction in hiring Ken Holland, who has had slightly more success than Dubas, with Connor McDavid and Leon Draisaitl in his stable. Are there any other legendary general managers hanging around 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 the NHL GMs played professional hockey. But some of the best — Julien BriseBois in Tampa, McCrimmon, Doug Armstrong — did not.

The challenge for Shanahan now is to keep to his original plan: How do you identify the best, with very little time, with so much at stake? The best GM in today’s NHL is arguably Boston’s Sweeney.

The days of the NHL being occupied by power players such as Harry Sinden, Glen Sather, Cliff Fletcher and Bill Torrey are no more. You can’t go and steal a Fletcher the way the Leafs managed in 1991. Or maybe you can.

Ujiri has to find a way to replace Nick Nurse, who was central to that fabulous championship run of 2019. Ujiri was enormous too in that victory. He traded for Kawhi Leonard when that seemed impossible. He traded at the deadline for Marc Gasol. If he doesn’t make those two moves, there is no run, no celebration. And if he doesn’t hire Nurse, the same is true.

Now he has a middle-of-the-pack NBA roster at a time when the Miami Heat will likely play for the championship. The Heat won 44 games this season. The Raptors won 41. One team seems close, the other so very far away. But this needs to be the summer of Ujiri: Hire the right coach, make the right trades, and make the Raptors significant again.

Toronto FC is so far away from that. This is Manning’s biggest mess. He is president of the soccer team and the CFL’s Argonauts. The Argos are coming off an unlikely Grey Cup win in a city that seems to shrug at the successes of its oldest franchise. The Argos’ problems are almost unsolvable. But with TFC, it’s about a product that is borderline terrible.

What’s more discouraging about TFC is that they have the second-worst record in MLS while spending the most on payroll. Cincinnati has the best record in the East. It pays its players $12 million. Second-place Nashville spends $5 million. TFC tops the league with $26 million in salaries.

That all adds up to two wins this season, none on the road, and the 28th-best record in a league of 29.

The TFC championship in 2017 and the Raptors title of 2019 seem so very long ago. Not as long ago as the Leafs’ last Stanley Cup, but that’s another story, always.

MLSE, with all its money and all its might, is facing challenging days for its team presidents.

Huge decisions await. Uncertainty is now the standard of the day.