Winners, Losers and the Toronto Maple Leafs: Evaluating the NHL Off-Season

The Toronto Maple Leafs are among the losers, unfortunately
May 4, 2024; Boston, Massachusetts, USA; Toronto Maple Leafs left wing Matthew Knies (23) and Boston Bruins right wing David Pastrnak (88) speak after the Bruins defeated the Leafs in overtime in game seven of the first round of the 2024 Stanley Cup Playoffs at TD Garden. Mandatory Credit: Bob DeChiara-USA TODAY Sports
May 4, 2024; Boston, Massachusetts, USA; Toronto Maple Leafs left wing Matthew Knies (23) and Boston Bruins right wing David Pastrnak (88) speak after the Bruins defeated the Leafs in overtime in game seven of the first round of the 2024 Stanley Cup Playoffs at TD Garden. Mandatory Credit: Bob DeChiara-USA TODAY Sports / Bob DeChiara-USA TODAY Sports
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The Worst Summer of Any Team In the NHL

It's not that the Toronto Maple Leafs made bad moves, it's that they do not understand the concept of risk vs reward.

Want to give Timothy Liljegren $3 million? Fine, but get some cheap years out of him. Only 2 years? What are they thinking? If they gave him $4 million but got some extra years that would clearly at least give them the chance of getting some team-friendly years.

If Liljegren ends up being worth the $3 million, they will just have to immediately extend or trade him, which means it's a bad contract.

Same exact thing with Joseph Woll. They are betting that a tandem of "maybes" is worth risking Auston Matthews prime over, but if it actually works out they won't get much value because Woll's deal is only for three years.

Woll has combined to play about a full season over the last four years and is an extreme injury risk, so giving him a guaranteed contract that doesn't the team a chance to cash in if they bet right just makes no sense.

Also, Nick Robertson, their top prospect, more or less, has asked for a trade.

The Leafs entered the off-season with a clear need to finally pair Auston Matthews and Mitch Marner with one of the NHL's best goalies. They failed.

They needed to upgrade on Pontus Holmber at 3C. They failed.

In fact, they lost Tyler Bertuzzi and their forward lines took a huge hit. If Robertson is also gone, that's two impact players lost and zero incoming.

They gave an objectively bad contract to Max Domi that was insanely long and which no other team would likely have even considered. Like all Leafs contracts, it begs the question "who were they negotiating against?"

The Leafs also needed to clear cap space by moving out the dead-weight on their roster but they also failed, as of now anyways, to do that.

The only thing they accomplished was improving their blue-line which they did by giving an injury prone 34 year-old a six-year contract, and doubling the salary of a 33 year-old third pairing vet they hope can now play in the top four. Apparently the Leafs are not interested in things like "up-side" and "value."

But their biggest problem is that they have no appetite for risk. The entire Toronto Maple Leafs front-office needs to sign up for a course in risk vs reward management.

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Weirdly, this could all work out because, like Edmonton, the pieces already in place are so good even a brutally unqualified GM can't screw it up too badly.