Pair of ex-Leafs GMs are now in nightmare job scenarios

It’s often said that being the general manager of the Toronto Maple Leafs is one of the hardest jobs in sports.

But what about the job you take after that one?

Well, a pair of former Leafs general managers are finding out the hard way that the grass isn’t always greener on the other side.

Kyle Dubas, now with the Pittsburgh Penguins, and Lou Lamoriello, now with the New York Islanders, are the last two men to hold one of the top executive jobs in Toronto.

Dubas was initially hired by Toronto’s front office in 2014 as an assistant GM, and Lamoriello joined in 2015.

Lamoriello was the general manager for three years before he left in 2018 and eventually ended up with the Islanders, with Dubas running the show from 2018 through his contract expiry in 2023 before he ended up in Pittsburgh less than a month later.

In both cases, there were less than ceremonious exits from Toronto.

The Leafs declined to renew Dubas’ contract in the week following a polarizing press conference where he admitted that he wasn’t totally sure about if his future was in Toronto and that the past year had taken a personal toll on him, while Lamoriello was pretty much given a handshake on the way out, with no real role for him in the up-and-comer Dubas’ front office.

Maybe their time in Toronto was up, but their chances of finding true NHL success in their new homes haven’t exactly been all that swell, either.

Lamoriello’s Islanders are currently down 3-0 in a playoff series to the Carolina Hurricanes, the same team who knocked them out of the first round a year prior.

And in the first year on the job, Dubas’ Penguins fell short of finishing in the top eight slots in the Eastern Conference, signalling a second straight year for that franchise without any postseason action.

And while neither team is horrible, that’s perhaps the problem. They’re both currently too far out of position to have a reasonable shot at a top pick via the NHL Draft Lottery and seem set on contending for a Stanley Cup with the group of players that they have.

A look at both rosters and their respective salary cap situations shows that both teams feature aging cores without a ton of young talent on the horizon.

The Islanders have 10 players (including two goalies) locked in through at least 2026, which doesn’t exactly give them the easiest flexibility in a tight salary cap world.

And if we’re being honest with ourselves, it’s unclear how much longer Lamoriello himself will be in charge, as the league’s oldest-ever general manager.

At 81 years old, Lamoriello is clearly in the job for nothing more than a pure passion for the game. While he might’ve won three Stanley Cups with the New Jersey Devils from 1995 through 2003, it’s hard to see him winning another one in New York.

The Penguins face a different contract puzzle.

Though they don’t have the litany of long-term deals that New York has, star players Sidney Crosby and Evgeni Malkin will be 36 and 37 years old when next season starts. With the team missing the playoffs each of the last two seasons, past history hasn’t exactly indicated they’re on the way up.

Unless you put on the rosiest of glasses, it’s hard to imagine a path back to contention for either franchise, despite clearly putting their best foot forward to construct winning rosters right now.

Being stuck in mediocrity is about the biggest nightmare scenario, but it’s one both former Leafs general managers currently find themselves in.