Toronto Maple Leafs: Who Are the Biggest Trade Deadline Losers?

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The Toronto Maple Leafs had a pretty good trade deadline.

Even as someone who isn’t a particular fan of anything the Toronto Maple Leafs did in the last month, it’s hard to be too critical.

They added a Selke winning, Conn Smythe winning ex-superstar who is only 31 and who could easily regain those heights. The risk is really only in the opportunity cost, since the acquisition cost of Ryan O’Reilly was dirt cheap.

(Criticism of rental players is misplaced, as its better to have cap-space than the vast majority of players).

They also added Jake McCabe, who is one of the NHL’s best players at preventing shots in the crease area, a noted weakness of the player he is replacing (Rasmus Sandin).

While I wish the Leafs did something more in line with what I was hoping for, I’m going to give the professionals the benefit of the doubt (sagacious, I know!) and see what happens. I still think they are probably the NHL’s best team (along with Carolina who is also outperforming their shot and save percentages).

But which NHL Teams dropped the ball at the Trade Deadline? Two in particular jump to mind.

WASHINGTON, DC – FEBRUARY 12: Erik Karlsson #65 (Photo by Scott Taetsch/Getty Images) /

The NHL’s Trade Deadline Losers (Not the Toronto Maple Leafs!)

The San Jose Sharks

You don’t want to be the first team to trade the Norris Trophy winning in the middle of the season, but come on.

Failing to move Erik Karlsson was an abject failure by a team who got a magical gift and threw it directly into the garbage.

Erik Karlsson found a time machine and is back to being the best defensemen since Nic Lidstrom retired. He could potentially hit 100 points. He has four more points at 5v5 than Connor McDavid (in one less game) to lead the NHL in the most important category.

He has a 56% Expected Goals rating on what without him would hockey’s worst team.

The fact that San Jose couldn’t/didn’t trade him is one of the biggest failures in NHL history.

The Toronto Maple Leafs supposedly looked into it and decided they couldn’t make the cap work. They should have tried harder, as there wasn’t another player within 100 miles of how good Karlsson is available.

Erik Karlsson has a 56% xGoals rating on what without him is the worst team in the NHL + leads the NHL in 5v5 points, with 4 more than McDavid has in 1 less game. He is going to win the Norris Trophy, and it's a shame he wasn't traded to a playoff team, specifically the Leafs.
— Editor in Leaf (@EditorinLeaf) March 7, 2023

Additionally, the Sharks traded superstar Timo. Meier to the Devils and all they got back was a B level prospect and three picks, include a very low first. What an awful return.

If you are reading this post, congratulations, you are qualified to be the GM of at least one NHL team. I didn’t think someone could make Ken Holland look good, but at least Mike Grier can say he’s a rookie, an excuse his counterpart in Tampa certainly can’t use.

William Nylander #88 of the Toronto Maple Leafs shoots past the defense of Erik Cernak #81 of the Tampa Bay Lightning (Photo by Mike Carlson/Getty Images) /

2. The Tampa Bay Lightning

Tanner Jeanott will go down as the weirdest, most inexplicable trade in NHL history.

I guess when you’ve won two Cups and gone to three straight finals, it’s pretty hard to doubt yourself, but Lightning GM Julien Brisebois should probably retire after making what has to be the single worst trade the NHL has seen in years.

Probably have to go back to Hall for Larson to see a trade whose failure was so instantly obvious.

Jeanoot netted the Predators a first round pick, a second round pick, a third round pick, a fourth round pick and a fifth round pick. And also former first round pick Cal Foote.

That amounts to almost an entire year’s picks (they are in different years) and a former top prospect (though one who is basically in bust territory).

Jeanott is about as good as Noel Acciari or Sam Lafferty, two players the Leafs picked up along with two borderline star players (with cap retention) for arguably less overall.

The Leafs paid 2 x firsts, 2 x seconds, and third + some duds, for McCabe, Lafferty, O’Reilly, Pillar and Acciari.

Compared to what the Leafs paid for their package of potential stars, Tampa paid about 10 x more. It is inexplicable.

If the Leafs kept one of those firsts and all the players, but they received just Acciari, that would be equal to what Tampa did.

Next. Leafs Top 10 Prospects. dark

And that is what makes Tampa the biggest loser at this year’s Trade Deadline, even a bigger loser than the Sharks.

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